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{{Chembox |
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{{Chembox |
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| verifiedrevid = 433356863 |
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| verifiedrevid = 446718238 |
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| Name = 2-Tolidine |
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| Name = 2-Tolidine |
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| Reference = <ref name="BGIA GESTIS">{{GESTIS|Name=ortho-Tolidin|ZVG=17950|CAS=119-93-7|Date=6.6.2008}}</ref> |
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| Reference = <ref name="BGIA GESTIS">{{GESTIS|Name=ortho-Tolidin|ZVG=17950|CAS=119-93-7|Date=6.6.2008}}</ref> |
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| ImageFile = 2-tolidine.svg |
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| ImageFile = 2-tolidine.svg |
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| ImageAlt = |
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| ImageSize = 200px |
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| PIN = 3,3′-Dimethyl--4,4′-diamine |
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| ImageAlt = |
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| OtherNames = ''o''-Tolidine; Orthotolidine; Diaminoditolyl; Diaminotolyl; Bianisidine; Tolidine blue; 3,3'-Dimethylbenzidine; 4,4'-Bi-''o''-] |
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| IUPACName = 4-(4-Amino-3-methylphenyl)-2-methylaniline |
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|Section1={{Chembox Identifiers |
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| OtherNames = ''o''-Tolidine; Orthotolidine; Diaminoditolyl; Diaminotolyl; Bianisidine; Tolidine blue; 3,3'-Dimethylbenzidine; 4,4'-Bi-''o''-toluidine |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 119-93-7 |
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| CASNo = 119-93-7 |
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| PubChem = 8413 |
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| ChEMBL = 85109 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 63HLO2IV6K |
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| PubChem = 8413 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C14443 |
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| KEGG = C14443 |
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| SMILES = CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N |
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| SMILES = CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N |
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| InChI = 1/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3 |
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| InChIKey = NUIURNJTPRWVAP-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = NUIURNJTPRWVAP-UHFFFAOYSA-N |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 34320 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8106 |
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| EINECS = 204-358-0 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=14|H=16|N=2 |
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| C=14 | H=16 | N=2 |
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| Appearance = |
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| Appearance = White to reddish crystals or powder |
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| Density = 1.23 g/cm<sup>3</sup> |
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| Density = 1.23 g/cm<sup>3</sup> |
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| MeltingPtC = 129 |
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| MeltingPtC = 129 |
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| BoilingPtC = 300.5 |
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| BoilingPtC = 300.5 |
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| Solubility = 1.3 g/L}} |
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| Solubility = 1.3 g/L}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = potential carcinogen |
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| FlashPt = 244 °C |
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| FlashPtC = 244 |
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| Autoignition = |
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| AutoignitionPtC = |
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| RPhrases = {{R45}} {{R22}} {{R51/53}} |
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| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| SPhrases = {{S53}} {{S45}} {{S61}} |
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| HPhrases = {{H-phrases|302|350|411}} |
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| PPhrases = {{P-phrases|201|202|264|270|273|281|301+312|308+313|330|391|405|501}} |
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| IDLH = Ca |
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| PEL = Handle with care |
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| REL = Ca C 0.02 mg/m<sup>3</sup> |
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'''2-Tolidine''' ('''orthotolidine''', '''o-tolidine'''; not to be confused with ]) is an organic compound with the chemical formula (C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)NH<sub>2</sub>)<sub>2</sub>. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms ] with acids, such as the ], which is commercially available. |
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'''Tolidine''' is a group of ]ic ]s, the most prevalent of which is 2-tolidine (''o''-tolidine). |
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2-Tolidine can be produced by many ] from a ] derivative derived from ].<ref>Noller, Carl R.: ''Textbook of Organic Chemistry'', Springer Verlag, 1960</ref> |
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==Chemistry== |
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:(CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>N<sub>2</sub>H<sub>2</sub> → (C<sub>6</sub>H<sub>3</sub>(CH<sub>3</sub>)NH<sub>2</sub>)<sub>2</sub> |
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2-Tolidine is slightly soluble in water (1.3 g/L) and has a melting point of 129 °C. It readily forms ] with acids, such as the ] which is commercially available. 2-Tolidine can be produced by a ] from a hydrazine derivative.<ref>Noller, Carl R.: ''Textbook of Organic Chemistry'', Springer Verlag, 1960</ref> |
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==Uses== |
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==Uses== |
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2-Tolidine is a commercially important ]s used mainly for dye production, but also for the production of certain ]rs. 2-Tolidine is an intermediate for the production of soluble ]s and insoluble pigments used particularly in the textile, leather and paper industries. |
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2-Tolidine ] is used mainly for dye production.<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{doi|10.1002/14356007.a20_371}}</ref> 2-Tolidine is an intermediate for the production of soluble ]s and insoluble pigments used particularly in the textile, leather and paper industries. |
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], a derivative of o-tolidine]] |
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It is also used for the production of certain ]s. |
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2-Tolidine also widely used as a reagent or indicator in analytical, clinical and forensic chemistry, such as in the analytical determination of gold. |
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2-Tolidine was widely used as a reagent or indicator in analytical, clinical and forensic chemistry, such as in the analytical determination of gold, or determination of the ] level in ] water. |
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==Safety== |
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==Safety== |
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2-Tolidine is toxic and possibly carcinogenic. It is listed as an ], meaning it is "possibly carcinogenic to humans". |
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2-Tolidine is toxic and possibly ]ic. It is listed as an ], meaning it is "possibly carcinogenic to humans". Animal studies have shown that animals exposed to tolidine developed tumors in the liver, kidney, and mammary glands.<ref>{{cite web |url=https://www.cdc.gov/niosh/npg/npgd0618.html |title=CDC - NIOSH Pocket Guide to Chemical Hazards - o-Tolidine |website=www.cdc.gov}}</ref> |
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==References== |
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==References== |
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