Tolidine

2-Tolidine[1]
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	119-93-7
PubChem	8413
KEGG	C14443 Y
Jmol-3D images	Image 1
SMILES CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N
Properties
Molecular formula	C14H16N2
Molar mass	212.29 g mol−1
Density	1.23 g/cm3
Melting point	129 °C, 402 K, 264 °F
Boiling point	300.5 °C, 574 K, 573 °F
Solubility in water	1.3 g/L
Hazards
R-phrases	R45 R22 R51/53
S-phrases	S53 S45 S61
Flash point	244 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[2]

Uses

2-Tolidine is a commercially important aromatic amines 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 from the IFA, accessed on 6.6.2008
2. ^ Noller, Carl R.: Textbook of Organic Chemistry, Springer Verlag, 1960