Tolidine
| Names | |
|---|---|
| Preferred IUPAC name
3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine | |
| Other names
o-Tolidine; Orthotolidine; Diaminoditolyl; Diaminotolyl; Bianisidine; Tolidine blue; 3,3'-Dimethylbenzidine; 4,4'-Bi-o-toluidine
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
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| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H16N2 | |
| Molar mass | 212.296 g·mol−1 |
| Appearance | White to reddish crystals or powder |
| Density | 1.23 g/cm3 |
| Melting point | 129 °C (264 °F; 402 K) |
| Boiling point | 300.5 °C (572.9 °F; 573.6 K) |
| 1.3 g/L | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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potential carcinogen |
| GHS labelling: | |
| GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard | |
| Danger | |
| H302, H350, H411 | |
| P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, P501 | |
| Flash point | 244 °C (471 °F; 517 K) |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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Handle with care |
REL (Recommended)
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Ca C 0.02 mg/m3 [60-minute] [skin] |
IDLH (Immediate danger)
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Ca [N.D.] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. 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 salts with acids, such as the hydrochloride, which is commercially available.
2-Tolidine can be produced by benzidine rearrangement from a hydrazone derivative of 2-nitrotoluene.[2]
- (CH3C6H4)2N2H2 → (C6H3(CH3)NH2)2
Uses
[edit | edit source]2-Tolidine is an aromatic amine used mainly for dye production.[3] 2-Tolidine is an intermediate for the production of soluble azo dyes and insoluble pigments used particularly in the textile, leather and paper industries.
It is also used for the production of certain elastomers.
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 chlorine level in swimming pool water.
Safety
[edit | edit source]2-Tolidine is toxic and possibly carcinogenic. It is listed as an IARC Group 2B carcinogen, 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.[4]
References
[edit | edit source]- ^ Record of ortho-Tolidin in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 6.6.2008.
- ^ Noller, Carl R.: Textbook of Organic Chemistry, Springer Verlag, 1960[verification needed][page needed]
- ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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