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Tolidine

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2-Tolidine
Names
IUPAC name 4-(4-Amino-3-methylphenyl)-2-methylaniline
Other names o-Tolidine; Orthotolidine; Diaminoditolyl; Diaminotolyl; Bianisidine; Tolidine blue; 3,3'-Dimethylbenzidine; 4,4'-Bi-o-toluidine
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.003.962 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N
Properties
Chemical formula C14H16N2
Molar mass 212.296 g·mol
Density 1.23 g/cm
Melting point 129 °C (264 °F; 402 K)
Boiling point 300.5 °C (572.9 °F; 573.6 K)
Solubility in water 1.3 g/L
Hazards
Flash point 244 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Tolidine is a group of isomeric organic compounds, the most prevalent of which is 2-tolidine (o-tolidine).

Chemistry

2-Tolidine is slightly soluble in water (1.3 g/L) and has a melting point of 129 °C. It readily forms salts with acids, such as the hydrochloride which is commercially available. 2-Tolidine can be produced by a benzidine rearrangement from a hydrazine derivative.

Uses

2-Tolidine is a commercially important aromatic amine used mainly for dye production, but also for the production of certain elastomers. 2-Tolidine is an intermediate for the production of soluble azo dyes and insoluble pigments used particularly in the textile, leather and paper industries.

2-Tolidine also widely used as a reagent or indicator in analytical, clinical and forensic chemistry, such as in the analytical determination of gold.

Safety

2-Tolidine is toxic and possibly carcinogenic. It is listed as an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans".

References

  1. Record of ortho-Tolidin in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 6.6.2008.
  2. Noller, Carl R.: Textbook of Organic Chemistry, Springer Verlag, 1960
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