Tolidine

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[1]
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.962
EC Number
  • 204-358-0
KEGG
UNII
  • InChI=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 ☒N
    Key: NUIURNJTPRWVAP-UHFFFAOYSA-N ☒N
  • 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
    Key: NUIURNJTPRWVAP-UHFFFAOYAK
  • CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N
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
 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)
 Handle with care
REL (Recommended)
 Ca C 0.02 mg/m3 [60-minute] [skin]
IDLH (Immediate danger)
 Ca [N.D.]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

2-Tolidine can be produced by many benzidine rearrangement from a hydrazine derivative derived from 2-nitrotoluene.[2]

(CH3C6H4)2N2H2 → (C6H3(CH3)NH2)2

Uses

2-Tolidine 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.

Pigment Yellow 16, a derivative of o-tolidine

It has also 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

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
  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
  3. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
  4. "CDC - NIOSH Pocket Guide to Chemical Hazards - o-Tolidine". www.cdc.gov.
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