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{{DISPLAYTITLE:''n''-Butylamine}} |
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{{DISPLAYTITLE:''n''-Butylamine}} |
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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 = 398782308 |
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|verifiedrevid = 412364052 |
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| Name = ''n''-Butylamine |
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|Name = ''n''-Butylamine |
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| ImageFile = N-Butylamine.svg |
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|ImageFile = N-Butylamine.svg |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = 150px |
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|ImageSize = 200 |
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| ImageName = ''n''-Butylamine |
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|ImageName = Skeletal formula of ''n''-butylamine |
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| IUPACName = butan-1-amine |
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|ImageFile1 = N-butylamine-from-xtal-1994-3D-balls.png |
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| OtherNames = NBA; Monobutylamime; 1-Butanamine; 1-Aminobutane |
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|ImageSize1 = 180 |
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| Section1 = {{Chembox Identifiers |
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|ImageAlt1 = Ball-and-stick model of the ''n''-butylamine molecule |
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| SMILES = NCCCC |
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|PIN = Butan-1-amine |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|OtherNames = {{Unbulleted list|1-Aminobutane|1-Butanamine|Monobutylamine |
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| ChemSpiderID = 7716 |
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| PubChem = 8007 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 13968 |
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| InChI = 1/C4H11N/c1-2-3-4-5/h2-5H2,1H3 |
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| InChIKey = HQABUPZFAYXKJW-UHFFFAOYAE |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HQABUPZFAYXKJW-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 109-73-9 |
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| RTECS = |
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| UNNumber = UN 1125 |
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}} |
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| Section2 = {{Chembox Properties |
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|C=4|H=11|N=1 |
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| Appearance = Colorless liquid |
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| Density = 0.74 g/cm<sup>3</sup> |
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| Solubility = Miscible |
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| MeltingPtC = -49 |
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| BoilingPtC = 77 |
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| pKa = 10.59<ref>{{cite journal | doi = 10.1021/ja01577a030 | author = Hall, H.K. | journal = J. Am. Chem. Soc. | year = 1957 | volume = 79 | pages = 5441}}</ref> |
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| Viscosity = 0.5 ] at 20 °C |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| MainHazards = Corrosive, if touched an cause smelling and taste problems and Highly flammable |
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| FlashPt = -14 °C |
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| RPhrases = {{R11}} {{R35}} {{R20}} {{R21}} {{R22}} |
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| SPhrases = {{S3}} {{S16}} {{S26}} {{S29}} {{S45}} {{S36}} {{S37}} {{S39}} |
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}} |
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| Section8 = {{Chembox Related |
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| OtherCpds = ]<br />]<br />]<br />]<br />] |
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}} |
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}} |
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}} |
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|Section1={{Chembox Identifiers |
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|Abbreviations = NBA |
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|CASNo = 109-73-9 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|PubChem = 8007 |
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|ChemSpiderID = 7716 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|UNII = N2QV60B4WR |
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|UNII_Ref = {{fdacite|changed|FDA}} |
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|EINECS = 203-699-2 |
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|UNNumber = 1125 |
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|DrugBank = DB03659 |
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|DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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|MeSHName = n-butylamine |
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|ChEBI = 43799 |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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|ChEMBL = 13968 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|RTECS = EO29750002 |
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|Beilstein = 605269 |
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|Gmelin = 1784 |
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|SMILES = CCCCN |
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|StdInChI = 1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = HQABUPZFAYXKJW-UHFFFAOYSA-N |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|Section2={{Chembox Properties |
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|C=4 | H=11 | N=1 |
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|Appearance = Colorless liquid |
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|Odor = fishy, ammoniacal |
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|Density = 740 mg ml<sup>−1</sup> |
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|MeltingPtK = 224 |
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|BoilingPtK = 350 to 352 |
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|Solubility = Miscible |
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|LogP = 1.056 |
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|VaporPressure = 9.1 kPa (at 20 °C) |
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|HenryConstant = 570 μmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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|pKb = 3.22 |
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|RefractIndex = 1.401 |
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|Viscosity = 500 µPa s (at 20 °C) |
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|MagSus = -58.9·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3={{Chembox Thermochemistry |
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|DeltaHf = −128.9–−126.5 kJ mol<sup>−1</sup> |
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|DeltaHc = −3.0196–−3.0174 MJ mol<sup>−1</sup> |
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|HeatCapacity = 188 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Hazards |
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|ExternalSDS = |
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|GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS exclamation mark}} |
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|GHSSignalWord = '''DANGER''' |
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|HPhrases = {{H-phrases|225|302|312|314|332}} |
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|PPhrases = {{P-phrases|210|280|305+351+338|310}} |
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|NFPA-F = 3 |
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|NFPA-H = 2 |
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|NFPA-R = 0 |
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|FlashPtC = -7 |
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|AutoignitionPtC = 312 |
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|ExploLimits = 1.7–9.8% |
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|LD50 = {{Unbulleted list|366 mg kg<sup>−1</sup> <small>(oral, rat)</small>|626 mg kg<sup>−1</sup> <small>(dermal, rabbit)</small>|430 mg kg<sup>−1</sup> <small>(oral, mouse)</small>|430 mg kg<sup>−1</sup> <small>(oral, guinea pig)</small>}}<ref name=IDLH>{{IDLH|109739|N-Butylamine}}</ref> |
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|PEL = C 5 ppm (15 mg/m<sup>3</sup>) <ref name=NIOSH>{{PGCH|0079}}</ref> |
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|IDLH = 300 ppm<ref name=NIOSH/> |
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|REL = C 5 ppm (15 mg/m<sup>3</sup>) <ref name=NIOSH/> |
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|LCLo = 4000 ppm (rat, 4 hr)<br/>263 ppm (mouse, 2 hr)<ref name=IDLH/> |
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}} |
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|Section5={{Chembox Related |
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|OtherFunction_label = alkanamines |
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|OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]|]|]}} |
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|OtherCompounds = ] |
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}} |
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}} |
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'''''n''-Butylamine''' is an organic compound (specifically, an ]) with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub>. This colourless liquid is one of the four ]ic ]s of ], the others being ], ], and ]. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Its vapours are heavier than air and it produces toxic oxides of nitrogen during combustion.<ref>{{Cite web|last=PubChem|title=Butylamine|url=https://pubchem.ncbi.nlm.nih.gov/compound/8007|access-date=2022-02-15|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref> |
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==Synthesis and reactions== |
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'''''n''-Butylamine''' is an organic compound (specifically, an ]) with the formula CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>. This colourless liquid is one of the four ]ic ]s of ], the others being ], ] and ]. At standard temperature and pressure, ''n''-butylamine is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. |
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It is produced by the reaction of ammonia and alcohols over ]: |
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:CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>OH + NH<sub>3</sub> → CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>NH<sub>2</sub> + H<sub>2</sub>O |
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''n''-Butylamine is a ]. The pK<sub>a</sub> of <sup>+</sup> is 10.78.<ref>{{cite journal|author=H. K. Hall, Jr.|year=1957|journal=J. Am. Chem. Soc.|volume=79|pages=5441–5444|title=Correlation of the Base Strengths of Amines|issue=20|doi=10.1021/ja01577a030}}</ref> |
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''n''-Butylamine exhibits reactions typical of other simple alkyl amines, i.e., alkylation, acylation, condensation with carbonyls. |
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It forms complexes with metal ions, examples being ''cis''- and ''trans''-.<ref>{{cite journal |doi=10.1016/j.ica.2003.10.039|title=Multinuclear NMR Study and Crystal Structures of Complexes of the Types ''cis''- and ''trans''-Pt(amine)''2''I''2''|year=2004|last1=Rochon|first1=Fernande D.|last2=Buculei|first2=Viorel|journal=Inorganica Chimica Acta|volume=357|issue=8|pages=2218–2230}}</ref> |
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==Uses== |
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==Uses== |
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].]] |
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This compound is used as an ingredient in the manufacture of ]s (such as ]s), ]s, and ]s. It is also a precursor for the manufacture of N,N'-dibutylthio], a rubber ] accelerator, and n-butylbenzenesulfonamide, a ] of ]. |
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This compound is used as an ingredient in the manufacture of ]s (such as ]s), ]s, and ]s. It is also a precursor for the manufacture of ], a rubber ] accelerator, and ''n''-butylbenzenesulfonamide, a ] of ]. It is used in the synthesis of ], the fungicide ], and ], and the ] ].<ref name=Ullmann>Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.{{doi|10.1002/14356007.a02_001}}</ref> |
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==Safety== |
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The ] to rats through the oral exposure route is 366 mg/kg.<ref>{{Cite web |url=https://us.vwr.com/stibo/hi_res/8235547.pdf |title=''n''-Butylamine MSDS |access-date=2013-11-12 |archive-url=https://web.archive.org/web/20131112205047/https://us.vwr.com/stibo/hi_res/8235547.pdf |archive-date=2013-11-12 |url-status=dead}}</ref> |
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In regards to occupational exposures to ''n''-butylamine, the ] and ] have set occupational exposure limits at a ceiling of 5 ppm (15 mg/m<sup>3</sup>) for dermal exposure.<ref></ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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==External links== |
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{{DEFAULTSORT:Butylamine, n-}} |
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*{{Commonscatinline|N-Butylamine}} |
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{{DEFAULTSORT:Butylamine, n-}} |
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