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{{Short description|Organic compound (C₆H₅NH₂); simplest aromatic amine}} |
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{{Other uses}} |
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{{Other uses}} |
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{{Distinguish|text = the amino acid ], or ]}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 408756658 |
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| verifiedrevid = 443390967 |
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| Name = Aniline |
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| ImageFileL1 = Aniline.svg |
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| Name = Aniline |
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| ImageFile = |
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| ImageSizeL1 = 100px |
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| ImageFileL1 = Structural formula of aniline.svg |
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| ImageNameL1 = Aniline |
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| ImageNameL1 = Structural formula of aniline |
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| ImageFileR1 = Aniline-3D-balls.png |
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| ImageClassL1 = skin-invert |
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| ImageSizeR1 = 150px |
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| ImageNameR1 = Aniline |
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| ImageFileR1 = Aniline-3D-vdW.png |
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| ImageSizeR1 = 140px |
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| IUPACName = Phenylamine |
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| ImageNameR1 = Aniline |
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| OtherNames = Aminobenzene<br/>Benzenamine<br/> |
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| PIN = Aniline<ref name=iupac2013>{{cite book |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) |publisher=] |date=2014 |location=Cambridge |pages=416, 668 |doi=10.1039/9781849733069-FP001 |isbn=978-0-85404-182-4 |quote=Aniline, for C<sub>6</sub>H<sub>5</sub>-NH<sub>2</sub>, is the only name for a primary amine retained as a preferred IUPAC name for which full substitution is permitted on the ring and the nitrogen atom. It is a Type 2a retained name; for the rules of substitution see P-15.1.8.2. Substitution is limited to substituent groups cited as prefixes in accordance with the seniority of functional groups explicitly expressed or implied in the functional parent compound name. The name benzenamine may be used in general nomenclature.}}</ref> |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = Benzenamine |
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| DrugBank = DB06728 |
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| OtherNames = Phenylamine<br/>Aminobenzene<br/>Benzamine<br/> |
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| IUPACName = |
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| Section1 = {{Chembox Identifiers |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB06728 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17296 |
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| ChEBI = 17296 |
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| SMILES = Nc1ccccc1 |
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| SMILES = Nc1ccccc1 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 538 |
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| ChEMBL = 538 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5889 |
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| ChemSpiderID = 5889 |
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| PubChem = 6115 |
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| PubChem1 = 8870 |
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| PubChem1_Comment = (]) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = SIR7XX2F1K |
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| UNII = SIR7XX2F1K |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 576R1193YL |
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| UNII1_Comment = (]) |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00292 |
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| KEGG = C00292 |
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| EC_number = 200-539-3 |
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| RTECS = BW6650000 |
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| UNNumber = 1547 |
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| Gmelin = 2796 |
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| Beilstein = 605631 |
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| 3DMet = B00082 |
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| InChI = 1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 |
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| InChI = 1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 |
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| InChIKey = PAYRUJLWNCNPSJ-UHFFFAOYAP |
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| InChIKey = PAYRUJLWNCNPSJ-UHFFFAOYAP |
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| StdInChIKey = PAYRUJLWNCNPSJ-UHFFFAOYSA-N |
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| StdInChIKey = PAYRUJLWNCNPSJ-UHFFFAOYSA-N |
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| CASNo = 62-53-3 |
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| CASNo = 62-53-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 142-04-1 |
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}} |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| Section2 = {{Chembox Properties |
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| CASNo1_Comment = (]) |
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| Formula = C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> |
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| MolarMass = 93.13 g/mol |
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| Appearance = colorless liquid |
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| Density = 1.0217 g/mL, liquid |
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| Solubility = 3.6 g/100 mL at 20°C |
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| SolubleOther = |
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| Solvent = ] |
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| MeltingPtC = -6.3 |
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| BoilingPtC = 184.13 |
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| pKb = 9.3 |
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| pKa = |
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| Viscosity = 3.71 ] (3.71 ] at 25 °C |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaHf = |
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| DeltaHc = -3394 kJ/mol |
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| Entropy = |
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}} |
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| Section7 = {{Chembox Hazards |
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| EUClass = Toxic ('''T''')<br />]<br />]<br />Dangerous for<br />the environment ('''N''') |
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| NFPA-H = 3 |
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| NFPA-F = 2 |
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| NFPA-R = |
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| RPhrases = {{R23/24/25}} {{R40}} {{R41}} {{R43}} {{R48/23/24/25}} {{R68}} {{R50}} |
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| SPhrases = {{S1/2}} {{S26}} {{S27}} {{S36/37/39}} {{S45}} {{S46}} {{S61}} {{S63}} |
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}} |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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| OtherFunctn = ]<br />] |
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| OtherCpds = ]<br />]<br />] |
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}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = {{chem2|C6H5NH2}} |
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| C=6|H=7|N=1 |
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| Appearance = Colorless liquid |
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| Density = 1.0297 g/mL |
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| Solubility = 3.6 g/(100 mL) at 20 °C |
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| SolubleOther = |
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| Solvent = ] |
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| MeltingPtC = −6.30 |
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| BoilingPtC = 184.13 |
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| pKa = {{unbulleted list |
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| 4.63 (conjugate acid; H<sub>2</sub>O)<ref name="VS">{{cite book |author1= Vollhardt, P. |author2= Schore, Neil |year=2018 |title=Organic Chemistry |edition=8th |publisher=W. H. Freeman |isbn=9781319079451 |page=1031}}</ref> |
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}} |
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| Viscosity = 3.71 ] (3.71 ] at 25 °C) |
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| VaporPressure = 0.6 mmHg (20 °C)<ref name=PGCH/> |
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| MagSus = −62.95·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| RefractIndex = 1.58364 |
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}} |
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| Section3 = |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaHf = |
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| DeltaHc = −3394 kJ/mol |
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| Entropy = |
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}} |
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| Section5 = |
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| Section6 = |
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| Section7 = {{Chembox Hazards |
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| NFPA-H = 3 |
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| NFPA-F = 2 |
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| NFPA-R = 0 |
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| NFPA_ref =<ref>{{cite web|url=https://cameochemicals.noaa.gov/chemical/2485|title=Aniline |publisher=US NOAA Office of Response and Restoration|website=cameochemicals.noaa.gov|access-date=2016-06-16}}</ref> |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}{{GHS09}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|317|318|331|341|351|372|400}} |
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| PPhrases = {{P-phrases|201|202|260|261|264|270|271|272|273|280|281|301+310|302+352|304+340|305+351+338|308+313|310|311|312|314|321|322|330|333+313|361|363|391|403+233|405|501}} |
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| FlashPtC = 70 |
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| AutoignitionPtC = 770 |
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| PEL = TWA 5 ppm (19 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0033}}</ref> |
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| MainHazards = potential occupational carcinogen |
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| REL = Ca <ref name=PGCH/> |
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| IDLH = 100 ppm<ref name=PGCH/> |
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| ExploLimits = 1.3–11%<ref name=PGCH/> |
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| LC50 = 175 ppm (mouse, 7 h)<ref name=IDLH>{{IDLH|62533|Aniline}}</ref> |
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| LCLo = 250 ppm (rat, 4 h)<br/>180 ppm (cat, 8 h)<ref name=IDLH/> |
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| LDLo = 195 mg/kg (dog, oral)<br/>250 mg/kg (rat, oral)<br/>464 mg/kg (mouse, oral)<br/>440 mg/kg (rat, oral)<br/>400 mg/kg (guinea pig, oral)<ref name=IDLH/> |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunction_label = ]s |
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| OtherFunction = ]<br/>] |
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| OtherCompounds = ]<br/>]<br/>] |
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}} |
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}} |
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'''Aniline''' ({{ety|pt|anil|]}}, and ''-ine'' indicating a derived substance)<ref>{{Cite web|title=aniline {{!}} Etymology, origin and meaning of aniline by etymonline|url=https://www.etymonline.com/word/aniline|access-date=2022-02-15|website=www.etymonline.com|language=en}}</ref> is an ] with the ] {{chem2|C6H5NH2}}. Consisting of a ] ({{chem2|\sC6H5}}) attached to an ] ({{chem2|\sNH2}}), aniline is the simplest ]. It is an industrially significant ], as well as a versatile starting material for ] synthesis. Its main use is in the manufacture of precursors to ], dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten ]. It ] readily, burning with a smoky flame characteristic of aromatic compounds.<ref name=Ullmann/> It is toxic to humans. |
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Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in ] reactions. Likewise, it is also prone to ]: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Aniline can be diazotized to give a ] salt, which can then undergo various nucleophilic substitution reactions. |
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Like other amines, aniline is both a ] (p''K''<sub>aH</sub> = 4.6) and a ], although less so than structurally similar ] amines. |
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Because an early source of the benzene from which they are derived was ], aniline dyes are also called '''coal tar dyes'''. |
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==Structure== |
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] of aniline from the ] at 252 K]] |
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===Aryl-N distances=== |
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In aniline, the C−N bond length is 1.41 ],<ref>{{Cite journal|last1=Zhang|first1=Huaiyu|last2=Jiang|first2=Xiaoyu|last3=Wu|first3=Wei|last4=Mo|first4=Yirong|date=April 28, 2016|title=Electron conjugation versus π-π repulsion in substituted benzenes: why the carbon-nitrogen bond in nitrobenzene is longer than in aniline|url=https://pubmed.ncbi.nlm.nih.gov/26852720/|journal=Physical Chemistry Chemical Physics|volume=18|issue=17|pages=11821–11828|doi=10.1039/c6cp00471g|issn=1463-9084|pmid=26852720|bibcode=2016PCCP...1811821Z}}</ref> compared to the C−N bond length of 1.47 Å for ],<ref>{{Cite journal|last1=Raczyńska|first1=Ewa D.|last2=Hallman|first2=Małgorzata|last3=Kolczyńska|first3=Katarzyna|last4=Stępniewski|first4=Tomasz M.|date=2010-07-12|title=On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems|journal=Symmetry|language=en|volume=2|issue=3|pages=1485–1509|doi=10.3390/sym2031485|bibcode=2010Symm....2.1485R|issn=2073-8994|doi-access=free}}</ref> indicating partial ] between C(aryl) and N.<ref>G. M. Wójcik "Structural Chemistry of Anilines" in Anilines (Patai's Chemistry of Functional Groups), S. Patai, Ed. 2007, Wiley-VCH, Weinheim. {{doi|10.1002/9780470682531.pat0385}}.</ref> The length of the ] of {{chem2|C(])\sNH2}} in anilines is highly sensitive to ]s. The C−N bond length is 1.34 Å in ] vs 1.44 Å in ].<ref>{{cite book |doi=10.1002/9780470771662.ch1|chapter=Structural chemistry |title=Amino, Nitrosco and Nitro Compounds and Their Derivatives: Vol. 1 (1982) |year=1982 |last1=Sorriso |first1=S. |pages=1–51 |isbn=9780470771662 }}</ref> |
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<!--Structural chemistry |
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S. Sorriso |
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Book Editor(s):Saul Patai |
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First published: 28 April 1982 https://doi-org.proxy2.library.illinois.edu/10.1002/9780470771662.ch1 |
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Book Series:PATAI'S Chemistry of Functional Groups--> |
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===Pyramidalization=== |
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The ] in anilines is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between ]. The nitrogen is described as having high p character. The amino group in aniline is flatter (i.e., it is a "shallower pyramid") than that in an aliphatic amine, owing to conjugation of the ] with the ] substituent. The observed geometry reflects a compromise between two competing factors: 1) stabilization of the N lone pair in an orbital with significant s character favors pyramidalization (orbitals with s character are lower in energy), while 2) ] of the N lone pair into the aryl ring favors planarity (a lone pair in a pure p orbital gives the best overlap with the orbitals of the benzene ring π system).<ref name=":0">{{Cite book|last=Alabugin, Igor V. |title=Stereoelectronic effects : a bridge between structure and reactivity|year=2016|isbn=978-1-118-90637-8|location=Chichester, UK|oclc=957525299}}</ref><ref>Alabugin I. V.; Manoharan, M.; Buck, M.; Clark, R. J. Substituted Anilines: The Tug-Of-War between Pyramidalization and Resonance Inside and Outside of Crystal Cavities. THEOCHEM, 2007, 813, 21-27. http://dx.doi.org/10.1016/j.theochem.2007.02.016.</ref> |
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Consistent with these factors, substituted anilines with electron donating groups are more pyramidalized, while those with electron withdrawing groups are more planar. In the parent aniline, the lone pair is approximately 12% s character, corresponding to sp<sup>7.3</sup> hybridization.<ref name=":0" />{{clarify|reason=Incorrect statement! The sp7.3 hybridization does not exist! What is this, a typo? Do you mean sp2.3 hybridization?|date=June 2023}} (For comparison, alkylamines generally have lone pairs in orbitals that are close to sp<sup>3</sup>.) |
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The pyramidalization angle between the C–N bond and the bisector of the H–N–H angle is 142.5°.<ref>{{cite book|title=Organic chemistry|last=Carey|first=Francis A.|date=2008|publisher=McGraw-Hill Higher Education|isbn=9780073047874|edition= 7th|location=Boston|oclc=71790138}}</ref> For comparison, in more strongly pyramidal amine group in ], this value is ~125°, while that of the amine group in ] has an angle of 180°. |
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'''Aniline''', '''phenylamine''' or '''aminobenzene''' is an ] with the ] C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub>. Consisting of a ] attached to an ], aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to ]. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. Aniline is colorless, but it slowly ] and resinifies in air, giving a red-brown tint to aged samples. |
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==Production== |
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==Production== |
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Industrial aniline production involves ] of ] (typically at 200–300 °C) in the presence of metal ]s:<ref>{{Cite patent|number=US3136818A|title=Production of aniline|gdate=1964-06-09|invent1=Heinrich|invent2=Guenter|invent3=Joachim|invent4=Anton|inventor1-first=Sperber|inventor2-first=Poehler|inventor3-first=Pistor Hans|inventor4-first=Wegerich|url=https://patents.google.com/patent/US3136818A/en}}</ref> Approximately 4 billion kilograms are produced annually. Catalysts include nickel, copper, palladium, and platinum,<ref name=Ullmann/> and newer catalysts continue to be discovered.<ref>{{cite journal |doi=10.1038/nchem.1645 |title=Heterogenized Cobalt Oxide Catalysts for Nitroarene Reduction by Pyrolysis of Molecularly Defined Complexes |date=2013 |last1=Westerhaus |first1=Felix A. |last2=Jagadeesh |first2=Rajenahally V. |last3=Wienhöfer |first3=Gerrit |last4=Pohl |first4=Marga-Martina |last5=Radnik |first5=Jörg |last6=Surkus |first6=Annette-Enrica |last7=Rabeah |first7=Jabor |last8=Junge |first8=Kathrin |last9=Junge |first9=Henrik |last10=Nielsen |first10=Martin |last11=Brückner |first11=Angelika |last12=Beller |first12=Matthias |journal=Nature Chemistry |volume=5 |issue=6 |pages=537–543 |pmid=23695637 |bibcode=2013NatCh...5..537W |s2cid=3273484 }}</ref> |
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Aniline is mainly produced in industry in two steps from ]. First, benzene is ] using a concentrated mixture of ] and ] at 50 to 60°C, which gives ]. In the second step, the nitrobenzene is ], typically at 200-300 °C in presence of various metal ]s: |
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:C<sub>6</sub>H<sub>5</sub>NO<sub>2</sub> + 3 H<sub>2</sub> → C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + 2 H<sub>2</sub>O |
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Originally, the reduction was effected with a mixture of ferrous chloride and iron metal via the ]. |
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:] |
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As an alternative, aniline is also prepared from ] and ammonia, the phenol being derived from the ].<ref name=Ullmann>Thomas Kahl, Kai-Wilfrid Schröder, F. R. Lawrence, W. J. Marshall, Hartmut Höke, Rudolf Jäckh "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry 2007; John Wiley & Sons: New York.{{DOI|10.1002/14356007.a02_303}}</ref> |
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The reduction of nitrobenzene to aniline was first performed by ] in 1842, using sulfide salts (]). The reduction of nitrobenzene to aniline was also performed as part of reductions by ] in 1854, using iron as the reductant (]). These stoichiometric routes remain useful for specialty anilines.<ref>{{Citation|last=Porter|first=H. K.|title=The Zinin Reduction of Nitroarenes|date=2011|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/0471264180.or020.04|work=Organic Reactions|pages=455–481|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/0471264180.or020.04|isbn=978-0-471-26418-7|access-date=2022-02-01}}</ref> |
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In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and ]s; and aniline oil for ], which contains aniline and ortho-], and is obtained from the ] (échappés) of the ] fusion.{{Citation needed|date=May 2010}} |
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Aniline can alternatively be prepared from ammonia and ] derived from the ].<ref name="Ullmann"/> |
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In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and ]s; and aniline oil for ], which contains aniline and ortho-] and is obtained from the ] (échappés) of the ] fusion.{{sfn|Chisholm|1911|p=48}} |
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===Related aniline derivatives=== |
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===Related aniline derivatives=== |
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Many analogues and ] of aniline are known where the phenyl group is further substituted. These include ]s, ]s, ]s, ]s, ]s, and many others. They also are usually prepared by nitration of the substituted aromatic compounds followed by reduction. For example, this approach is used to convert ] into toluidines and ] into ].<ref name="Ullmann"/> Alternatively, using Buchwald-Hartwig coupling or Ullmann reaction approaches, aryl halides can be aminated with aqueous or gaseous ammonia.<ref>{{Cite web|url=https://www.organic-chemistry.org/synthesis/C1N/amines/anilines.shtm|title = Aniline synthesis by amination (Arylation)}}</ref> |
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Many derivatives of aniline can be prepared in similar fashion from nitrated aromatic compounds. Nitration followed by reduction of ] affords ]s. Nitration of ] and related derivatives and reduction of the nitration products gives aniline derivatives, e.g. ]. |
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==Reactions== |
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==Reactions== |
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The chemistry of aniline is extremely rich because the compound has been cheaply available for many years. Below are some classes of its reactions. |
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The chemistry of aniline is rich because the compound has been cheaply available for many years. Below are some classes of its reactions. |
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===Oxidation=== |
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===Oxidation=== |
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], a colorless liquid when pure, illustrating the tendency of anilines to air-oxidize to dark-colored products.]] |
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The oxidation of aniline has been heavily investigated, and can result in reactions localized at nitrogen or more commonly results in the formation of new C-N bonds. In alkaline solution, ] results, whereas ] produces the violet-coloring matter violaniline. ] converts it into ], whereas ], in the presence of certain metallic salts (especially of ]), give "aniline black". Hydrochloric acid and potassium chlorate give ]. ] in neutral solution oxidizes it to ], in alkaline solution to ], ammonia and ], in acid solution to aniline black. ] gives ] and para-amino ]. Oxidation with persulfate affords a variety of ]s compounds. These polymers exhibit rich redox and acid-base properties. |
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The oxidation of aniline has been heavily investigated, and can result in reactions localized at nitrogen or more commonly results in the formation of new C-N bonds. In alkaline solution, ] results, whereas ] produces the violet-coloring matter violaniline. ] converts it into ], whereas ]s, in the presence of certain metallic salts (especially of ]), give ]. Hydrochloric acid and potassium chlorate give ]. ] in neutral solution oxidizes it to ]; in alkaline solution to ], ammonia, and ]; in acid solution to aniline black. ] gives ] and para-amino ].{{sfn|Chisholm|1911|p=48}} Oxidation with ] affords a variety of ]s. These polymers exhibit rich redox and acid-base properties. |
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]s can form upon oxidation of aniline.]] |
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===Electrophilic reactions at carbon=== |
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===Electrophilic reactions at ortho- and para- positions=== |
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Like ]s, aniline derivatives are highly susceptible to ] reactions. Its high reactivity reflects that it is an ], which enhances the electron-donating ability of the ring. For example, reaction of aniline with ] at 180 °C produces ], H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>SO<sub>3</sub>H, which can be converted to ]. Sulfanilamide is one of the ]s, which were widely used as ]s in the early 20th century. The largest scale industrial reaction of aniline involves its alkylation with ]: |
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Like ]s, aniline derivatives are highly susceptible to ] reactions. Its high reactivity reflects that it is an ], which enhances the electron-donating ability of the ring. For example, reaction of aniline with ] at 180 °C produces ], {{chem2|H2NC6H4SO3H}}. |
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:2 C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + CH<sub>2</sub>O → CH<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>)<sub>2</sub> + H<sub>2</sub>O |
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If bromine water is added to aniline, the ] is decolourised and a white ] of ] is formed. To generate the mono-substituted product, a ] with acetyl chloride is required: |
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] |
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The reaction to form ] is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline. |
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The largest scale industrial reaction of aniline involves its alkylation with ]. An idealized equation is shown: |
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:{{chem2|2 C6H5NH2 + CH2O → CH2(C6H4NH2)2 + H2O}} |
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The resulting diamine is the precursor to ] and related diisocyanates. |
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The resulting diamine is the precursor to ] and related diisocyanates. |
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===Reactions at nitrogen=== |
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===Reactions at nitrogen=== |
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====Basicity==== |
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====Basicity==== |
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Aniline is a weak ]. ]s such as aniline are, in general, much weaker bases than ] amines because of the electron-withdrawing effect of the phenyl group. Aniline reacts with strong acids to form ''']''' (or phenylammonium) ion (C<sub>6</sub>H<sub>5</sub>-NH<sub>3</sub><sup>+</sup>).<ref>{{McMurry3rd}}</ref> The ] forms white plates. Although aniline is weakly basic, it ] ], ], and ] salts, and, on warming, expels ] from its salts. The weak basicity is due to a negative inductive effect as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring. |
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Aniline is a weak ]. ]s such as aniline are, in general, much weaker bases than ] amines. Aniline reacts with strong acids to form the ] (or phenylammonium) ion ({{chem2|C6H5\sNH3+}}).<ref>{{McMurry3rd}}</ref> |
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Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp<sup>2</sup> carbon and resonance effects, as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring. (see the picture below): |
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] |
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Missing in such an analysis is consideration of ]. Aniline is, for example, more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution.<ref>{{March6th}}</ref> |
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====Acylation==== |
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====Acylation==== |
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{{Main|Anilide}} |
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Aniline reacts with carboxylic acids<ref>{{OrgSynth | author = Carl N. Webb | title = Benzanilide | |collvol = 1 | collvolpages = 82 | year = 1941 | prep = cv1p0082}}</ref> or more readily with ]s such as ] to give ]s. The amides formed from aniline are sometimes called '''anilides''', for example CH<sub>3</sub>-CO-NH-C<sub>6</sub>H<sub>5</sub> is ]. Antifebrin (acetanilide), an anti-pyretic and analgesic, is obtained by the reaction of ] and aniline. |
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Aniline reacts with ]s such as ] to give ]s. The amides formed from aniline are sometimes called ]s, for example {{chem2|CH3\sC(\dO)\sNH\sC6H5}} is ]. At high temperatures aniline and carboxylic acids react to give the anilides.<ref>{{OrgSynth|author=Carl N. Webb|title= Benzanilide |collvol=1|collvolpages=82|year=1941|prep=cv1p0082}}</ref> |
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====''N''-Alkylation==== |
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====''N''-Alkylation==== |
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N-methylation of aniline with ] at elevated temperatures over acid catalsts gives ''N''-methylaniline and ]: |
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''N''-Methylation of aniline with ] at elevated temperatures over ] gives ] and ]: |
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:{{chem2|C6H5NH2 + 2 CH3OH → C6H5N(CH3)2 + 2H2O}} |
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:C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + 2 CH<sub>3</sub>OH → C<sub>6</sub>H<sub>4</sub>N(CH<sub>3</sub>)<sub>2</sub> + H<sub>2</sub>O |
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Methyl and dimethylaniline are colourless liquids with ] of 193-195 °C and 192 °C, respectively. These derivatives are of importance in the colour industry. Aniline combines directly with ]s to form secondary and tertiary amines. |
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''N''-Methylaniline and ''N'',''N''-dimethylaniline are colorless liquids with ]s of 193–195 °C and 192 °C, respectively. These derivatives are of importance in the color industry. |
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====Carbon disulfide derivatives==== |
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====Carbon disulfide derivatives==== |
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Boiled with ], it gives sulfocarbanilide (diphenyl]) (CS(NHC<sub>6</sub>H<sub>5</sub>)<sub>2</sub>), which may be decomposed into phenyl ](C<sub>6</sub>H<sub>5</sub>CNS), and triphenyl ] (C<sub>6</sub>H<sub>5</sub>N=C(NHC<sub>6</sub>H<sub>5</sub>)<sub>2</sub>). |
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Boiled with ], it gives sulfocarbanilide (diphenyl]) ({{chem2|S\dC(\sNH\sC6H5)2}}), which may be decomposed into phenyl ] ({{chem2|C6H5\sN\dC\dS}}), and triphenyl ] ({{chem2|C6H5\sN\dC(\sNH\sC6H5)2}}).{{sfn|Chisholm|1911|p=48}} |
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====Diazotization==== |
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====Diazotization==== |
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Aniline and its ring-substituted derivatives react with ] to form ]s. Through these intermediates, aniline can be conveniently converted to -OH, -CN, or a ] via ]s. This diazonium salt can also be reacted with NaNO2 and phenol which produces a dye which is benzeneazophenol, this process is called coupling. |
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Aniline and its ring-substituted derivatives react with ] to form ]s. One example is ]. Through these intermediates, the amine group can be converted to a ] ({{chem2|\sOH}}), ] ({{chem2|\sCN}}), or ] group ({{chem2|\sX}}, where X is a ]) via ]s. This diazonium salt can also be reacted with ] and ] to produce a ] known as ], in a process called '']''. |
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The reaction of converting ] ] amine into diazonium salt is called diazotisation. |
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In this reaction primary aromatic amine is allowed to react with ] and 2 moles of ], which is known as "ice cold mixture" because the temperature for the reaction was as low as 0.5 °C. The benzene diazonium salt is formed as major product alongside the byproducts ] and ]. |
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===Other reactions=== |
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===Other reactions=== |
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It reacts with nitrobenzene to produce ] in the ]. Hydrogenation gives ]. |
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It reacts with nitrobenzene to produce ] in the ]. Hydrogenation gives ]. |
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Being a standard reagent in laboratories, aniline is used for many niche reactions. Its acetate is used in the ] for carbohydrates, identifying pentoses by conversion to ]. It is used to stain neural ] blue in the ].{{Citation needed|date=May 2010}} |
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Being a standard reagent in laboratories, aniline is used for many niche reactions. Its acetate is used in the ] for carbohydrates, identifying pentoses by conversion to ]. It is used to stain neural ] blue in the ].{{Citation needed|date=May 2010}} |
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In addition, aniline is the starting component in the production of ].<ref name="Panda 2019 38">{{Cite book |last=Panda |first=Dr H |title=Epoxy Resins Technology Handbook (Manufacturing Process, Synthesis, Epoxy Resin Adhesives and Epoxy Coatings |publisher=Asia Pacific Business Press Inc |year=2019 |isbn=978-8178331829 |edition=2nd |pages=38}}</ref> ] is the other main ingredient.<ref name="Panda 2019 38"/><ref>{{Cite journal |last1=Jung |first1=Woo-Hyuk |last2=Ha |first2=Eun-Ju |last3=Chung |first3=Il doo |last4=Lee |first4=Jang-Oo |date=2008-08-01 |title=Synthesis of aniline-based azopolymers for surface relief grating |url=https://doi.org/10.1007/BF03218555 |journal=Macromolecular Research |language=en |volume=16 |issue=6 |pages=532–538 |doi=10.1007/BF03218555 |s2cid=94372490 |issn=2092-7673}}</ref> |
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==Uses== |
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==Uses== |
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Aniline is predominantly used for the preparation of methylenedianiline and related compounds by condensation with formaldehyde. The diamines are condensed with ] to give ], a precursor to urethane polymers.<ref name="Ullmann">{{cite book |last1=Kahl |first1=Thomas |url=https://books.google.com/books?id=qGc2yQEACAAJ |title=Ullmann's encyclopedia of industrial chemistry |last2=Schröder |first2=K. W. |last3=Lawrence |first3=F. R. |last4=Elvers |first4=Barbara |last5=Höke |first5=Hartmut |last6=Pfefferkorn |first6=R. |last7=Marshall |first7=W. J. |publisher=Wiley: New York |year=2007 |isbn=978-3-527-20138-9 |editor-last=Ullmann |editor-first=Fritz |chapter=Aniline |doi=10.1002/14356007.a02_303 |oclc=11469727}}</ref> |
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The largest application of aniline is for the preparation of ] (MDI). The majority of aniline serves this market. Other uses include ] processing chemicals (9%), ] (2%), and dyes and pigments (2%).<ref name="CPoA">{{cite news|title=Aniline|publisher=The Chemical Market Reporter|url=http://www.the-innovation-group.com/ChemProfiles/Aniline.htm|accessdate=2007-12-21}}</ref> As additives to rubber, aniline derivatives such as ]{{Disambiguation needed|date=June 2011}} and ], are antioxidants. Illustrative of the drugs prepared from aniline is ] (acetaminophen, ]). The principal use of aniline in the dye industry is as a precursor to ], the blue of ].<ref name=Ullmann/> |
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:], a precursor to polyurethanes.]] |
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Other uses include ] processing chemicals (9%), ]s (2%), and dyes and pigments (2%).<ref name="CPoA">{{cite news|title=Aniline|publisher=The Chemical Market Reporter |url=http://www.the-innovation-group.com/ChemProfiles/Aniline.htm|access-date=2007-12-21 |url-status=dead |archive-url=https://archive.today/20020219104231/http://www.the-innovation-group.com/ChemProfiles/Aniline.htm|archive-date=2002-02-19}}</ref> As additives to rubber, aniline derivatives such as ]s and ], are antioxidants. Illustrative of the drugs prepared from aniline is ] (acetaminophen, ]). The principal use of aniline in the dye industry is as a precursor to ], the blue of ].<ref name=Ullmann/> |
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Aniline is also used at a smaller scale in the production of the ] ]. |
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], which is prepared from aniline.]] |
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Aniline oil is also used for mushroom identification. |
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Kerrigan's 2016 Agaricus of North America P45: (Referring to Schaffer's reaction) "In fact I recommend switching to the following modified test. Frank (1988) developed an alternative formulation in which aniline oil is combined with glacial acetic acid (GAA, essentially distilled vinegar) in a 50:50 solution. GAA is a much safer, less reactive acid. This single combined reagent is relatively stable over time. A single spot or line applied to the pileus (or other surface). In my experience the newer formulation works as well as Schaffer's while being safer and more convenient."<ref>Kerrigan, Richard (2016). Agaricus of North America. NYBG Press. p. 45. ISBN 978-0-89327-536-5.</ref> |
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==History== |
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==History== |
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Aniline was first isolated from the destructive distillation of ] in 1826 by ],<ref>{{cite journal |
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Aniline was first isolated in 1826 by ] by ] of ].<ref>{{cite journal |
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| title = Ueber das Verhalten der organischen Körper in höheren Temperaturen |
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|title=Ueber das Verhalten der organischen Körper in höheren Temperaturen |
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|trans-title=On the behaviour of organic substances at high temperatures |
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| author = Otto Unverdorben |
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|author=Otto Unverdorben |
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| journal = ] |
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|journal=Annalen der Physik und Chemie |
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| volume = 84 |
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|volume=8 |
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| issue = 11 |
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| pages = 397–410 |
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|pages=397–410 |
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| year = 1826 |
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|year=1826 |
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|url=https://books.google.com/books?id=zx0AAAAAMAAJ&pg=PA397 |
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|doi=10.1002/andp.18260841109|bibcode=1826AnP....84..397U |
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| doi = 10.1002/andp.18260841109}}</ref> who named it crystalline. In 1834, ] (''Pogg. Ann.'', 1834, 31, p. 65; 32, p. 331) isolated from ] a substance that produced a beautiful blue colour on treatment with ], which he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that, by treating indigo with caustic potash, it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, from ] anil "the indigo shrub" from ] an-nil "the indigo" assimilated from al-nil, from Persian nila, from nili "indigo" with ''Indigofera anil'', anil being derived from the Sanskrit ''नीली'' ''nīla'', dark-blue, and ''nīlā'',<ref>http://www.etymonline.com/index.php?term=aniline</ref> the indigo plant. About the same time ] found that, on reducing nitrobenzene, a base was formed, which he named benzidam. ] investigated these variously-prepared substances, and proved them to be identical (1855), and thenceforth they took their place as one body, under the name aniline or phenylamine. |
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|issue =11}}</ref> He called it ''Crystallin''. In 1834, ] isolated a substance from ] that turned a beautiful blue color when treated with ]. He named it ''kyanol'' or ''cyanol''.<ref>F. F. Runge (1834) "Ueber einige Produkte der Steinkohlendestillation" (On some products of coal distillation), ''Annalen der Physik und Chemie'', '''31''': (see page 65), ; and '''32''': (see page 331).</ref> In 1840, ] (1808–1871) treated indigo with ] and obtained an oil that he named ''aniline'', after an indigo-yielding plant, anil ('']'').<ref>J. Fritzsche (1840) (On aniline, a new decomposition product of indigo), ''Bulletin Scientifique'' , '''7''' (12): 161–165. Reprinted in: |
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*J. Fritzsche (1840) "Ueber das Anilin, ein neues Zersetzungsproduct des Indigo", ''Justus Liebigs Annalen der Chemie'', '''36''' (1): 84–90. |
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*J. Fritzsche (1840) , ''Journal für praktische Chemie'', '''20''': 453–457. In a postscript to this article, Erdmann (one of the journal's editors) argues that aniline and the "cristallin", which was found by Unverdorben in 1826, are the same substance; see .</ref><ref>synonym , ultimately from Sanskrit "nīla", dark-blue.</ref> In 1842, ] reduced ] and obtained a base that he named ''benzidam''.<ref>N. Zinin (1842). "Beschreibung einiger neuer organischer Basen, dargestellt durch die Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure" (Description of some new organic bases, produced by the action of hydrogen sulfide on compounds of hydrocarbons and hyponitric acid ), ''Bulletin Scientifique'' , '''10''' (18): 272–285. Reprinted in: N. Zinin (1842) , ''Journal für praktische Chemie'', '''27''' (1): 140–153. Benzidam is named on page 150. |
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Fritzsche, Zinin's colleague, soon recognized that "benzidam" was actually aniline. See: Fritzsche (1842) ''Bulletin Scientifique'', '''10''': 352. Reprinted as a postscript to Zinin's article in: J. Fritzsche (1842) (Comment on the preceding article by Mr. Zinin), ''Journal für praktische Chemie'', '''27''' (1): 153.<br/> |
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See also: (Anon.) (1842) (Organic bases originating from nitronaphthalene and nitrobenzene via hydrogen sulfide), ''Annalen der Chemie und Pharmacie'', '''44''': 283–287.</ref> In 1843, ] showed that these were all the same substance, known thereafter as ''phenylamine'' or ''aniline''.<ref>August Wilhelm Hofmann (1843) (Chemical investigation of organic bases in coal tar oil), ''Annalen der Chemie und Pharmacie'', '''47''': 37–87. On page 48, Hofmann argues that krystallin, kyanol, benzidam, and aniline are identical.</ref> |
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===Synthetic dye industry=== |
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The great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, ]stuffs. The discovery of ] in 1856 by ] was the first of a series of an enormous range of dyestuffs, such as ], safranine and induline. Its first industrial-scale use was in the manufacture of ], a ] dye discovered in 1856 by Hofmann's student ]. At the time of mauveine's discovery, aniline was an expensive laboratory compound, but it was soon prepared "by the ton" using a process previously discovered by ].<ref>Perkin, William Henry. 1861-06-08. ''The Chemical News and Journal of Industrial Science''. Retrieved on 2007-09-24.</ref> The synthetic dye industry grew rapidly as new aniline-based dyes were discovered in the late 1850s and 1860s. |
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In 1856, while trying to synthesise ], ]'s student ] discovered ]. Mauveine quickly became a commercial dye. Other ] dyes followed, such as ], ], and ]. At the time of mauveine's discovery, aniline was expensive. Soon thereafter, applying a method reported in 1854 by ],<ref>A. Béchamp (1854) (On the action of iron protosalts on nitronaphthaline and nitrobenzene. New method of forming Zinin's synthetic organic bases.), ''Annales de Chemie et de Physique'', 3rd series, '''42''': 186 – 196. (Note: In the case of a metal having two or more distinct oxides (e.g., iron), a "protosalt" is an obsolete term for a salt that is obtained from the oxide containing the lowest proportion of oxygen to metal; e.g., in the case of iron, which has two oxides – iron (II) oxide (FeO) and iron (III) oxide (Fe<sub>2</sub>O<sub>3</sub>) – FeO is the "protoxide" from which protosalts can be made. See: ].)</ref> it was prepared "by the ton".<ref>Perkin, William Henry. 1861-06-08. . ''The Chemical News and Journal of Industrial Science''. Retrieved on 2007-09-24.</ref> The ] enabled the evolution of a massive dye industry in Germany. Today, the name of ], originally ''Badische Anilin- und Soda-Fabrik'' (English: ] Aniline and ] Factory), now the largest chemical supplier, echoes the legacy of the synthetic dye industry, built via aniline dyes and extended via the related ]s. The first azo dye was ].<ref>Auerbach G, "Azo and naphthol dyes", ''Textile Colorist'', 1880 May;'''2'''(17):137-9, .</ref> |
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{{Further|Nigrosene}} |
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===Developments in medicine=== |
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==Toxicology== |
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In the late 19th century, derivatives of aniline such as ] and ] emerged as ] drugs, with their cardiac-suppressive ] often countered with ].<ref>Wilcox RW, "The treatment of influenza in adults", ''Medical News'', 1900 Dec 15;'''77'''():931-2, .</ref> During the first decade of the 20th century, while trying to modify synthetic dyes to treat ], ] – who had coined the term '']'' for his '']'' approach to medicine – failed and switched to modifying ]'s ], the first organic ]al drug, and serendipitously obtained a treatment for ] – ] – the first successful chemotherapy agent. ], not yet recognized as a bacterium, was still thought to be a parasite, and medical bacteriologists, believing that bacteria were not susceptible to the chemotherapeutic approach, overlooked ]'s report in 1928 on the effects of ].<ref name=Wagener>D J Th Wagener, ''The History of Oncology'' (Houten: Springer, 2009), .</ref> |
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Aniline is toxic by inhalation of the vapour.<ref name="HitCL">Muir, GD (ed.) 1971, ''Hazards in the Chemical Laboratory'', The Royal Institute of Chemistry, London.</ref> The ] lists it in ] (''not classifiable as to its carcinogenicity to humans'') due to the limited and contradictory data available. The early manufacture of aniline resulted in increased incidents of |
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bladder cancer, but these effects are now attributed to naphthylamines, not anilines.<ref name=Ullmann/> |
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In 1932, ] sought medical applications of its dyes. ] identified as an ] a red azo dye, introduced in 1935 as the first antibacterial drug, ], soon found at ] to be a ] degraded '']'' into ] – a colorless intermediate for many, highly ] azo dyes – already with an expired patent, synthesized in 1908 in Vienna by the researcher ] for his doctoral research.<ref name=Wagener/> By the 1940s, over 500 related ]s were produced.<ref name=Wagener/> Medications in high demand during ] (1939–45), these first ''miracle drugs'', chemotherapy of wide effectiveness, propelled the American pharmaceutics industry.<ref>John E Lesch, ''The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine'' (New York: Oxford University Press, 2007), .</ref> In 1939, at ], seeking an alternative to sulfa drugs, ] developed Fleming's penicillin into the first systemic ] drug, ]. (], developed by ] at ] in 1939, was the first antibiotic, yet its toxicity restricted it to ] use.) After World War II, ] introduced the chemotherapeutic approach to cancer treatment.<ref>{{cite magazine | title=Medicine: Spoils of War | magazine=] | date=15 May 1950 | url=http://www.time.com/time/magazine/article/0,9171,820604,00.html | archive-url=https://web.archive.org/web/20130624131223/http://www.time.com/time/magazine/article/0,9171,820604,00.html | archive-date=24 June 2013 | url-status=dead | access-date=20 November 2020}}</ref> |
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===Rocket fuel=== |
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Some early American rockets, such as the ] and ], used a mixture of aniline and ] as a fuel, with ] as an oxidizer. The combination is ], igniting on contact between fuel and oxidizer. It is also dense, and can be stored for extended periods. Aniline was later replaced by ].<ref name="Corporal">Brian Burnell. 2016. http://www.nuclear-weapons.info/cde.htm#Corporal SSM</ref> |
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==Toxicology and testing== |
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Aniline is toxic by inhalation of the vapour, ingestion, or percutaneous absorption.<ref name="HitCL">Muir, GD (ed.) 1971, ''Hazards in the Chemical Laboratory'', The Royal Institute of Chemistry, London.</ref><ref>''The Merck Index''. 10th ed. (1983), p.96, Rahway: Merck & Co.</ref> The ] lists it in ] (''Probably carcinogenic to humans''), and it has specifically been linked to bladder cancer.<ref>{{Cite journal |doi=10.1155/2011/528353|title=Pathobiology and Chemoprevention of Bladder Cancer|year=2011|last1=Tanaka|first1=Takuji|last2=Miyazawa|first2=Katsuhito|last3=Tsukamoto|first3=Testuya|last4=Kuno|first4=Toshiya|last5=Suzuki|first5=Koji |journal=Journal of Oncology|volume=2011|pages=1–23 |doi-access=free |pmid=21941546 }}</ref> |
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Aniline has been implicated as one possible cause of ].<ref name="Krahl1988">Krahl-Urban, B., Papke, H.E., Peters, K. (1988) ''Forest Decline: Cause-Effect Research in the United States of North America and Federal Republic of Germany''. Germany: Assessment Group for Biology, Ecology and Energy of the Julich Nuclear Research Center.</ref> |
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Many methods exist for the detection of aniline.<ref>''Basic Analytical Toxicology'' (1995), R. J. Flanagan, S. S. Brown, F. A. de Wolff, R. A. Braithwaite, B. Widdop: World Health Organization</ref> |
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===Oxidative DNA damage=== |
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Exposure of rats to aniline can elicit a response that is toxic to the ], including a ] response.<ref name="Ma2008">{{Cite journal |doi=10.1016/j.taap.2008.08.010 |pmc=2614128 |pmid=18793663|title=Oxidative DNA damage and its repair in rat spleen following subchronic exposure to aniline |year=2008 |last1=Ma |first1=Huaxian |last2=Wang |first2=Jianling |last3=Abdel-Rahman |first3=Sherif Z. |last4=Boor |first4=Paul J. |last5=Khan |first5=M. Firoze |journal=Toxicology and Applied Pharmacology |volume=233 |issue=2 |pages=247–253 }}</ref> Rats exposed to aniline in drinking water, showed a significant increase in oxidative ] to the spleen, detected as a 2.8-fold increase in ] in their ].<ref name = Ma2008/> Although the ] pathway was also activated, its activity was not sufficient to prevent the accumulation of 8-OHdG. The accumulation of oxidative DNA damages in the spleen following exposure to aniline may increase mutagenic events that underlie tumorigenesis. |
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==Notes== |
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{{Reflist|30em}} |
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==References== |
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==References== |
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*{{EB1911 |mode=cs2 |wstitle=Aniline |volume=2 |pages=47–48}} |
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==External links== |
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==External links== |
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{{Wiktionary}} |
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{{commons|Aniline|Aniline}} |
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{{Commons}} |
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