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Tolidine

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(Redirected from 3,3'-Dimethylbenzidine)
2-Tolidine
Names
Preferred IUPAC name 3,3′-Dimethyl--4,4′-diamine
Other names o-Tolidine; Orthotolidine; Diaminoditolyl; Diaminotolyl; Bianisidine; Tolidine blue; 3,3'-Dimethylbenzidine; 4,4'-Bi-o-toluidine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.962 Edit this at Wikidata
EC Number
  • 204-358-0
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3Key: NUIURNJTPRWVAP-UHFFFAOYSA-N
  • InChI=1/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3Key: NUIURNJTPRWVAP-UHFFFAOYAK
SMILES
  • CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N
Properties
Chemical formula C14H16N2
Molar mass 212.296 g·mol
Appearance White to reddish crystals or powder
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
Occupational safety and health (OHS/OSH):
Main hazards potential carcinogen
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H302, H350, H411
Precautionary statements 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/m
IDLH (Immediate danger) Ca
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 many benzidine rearrangement from a hydrazine derivative derived from 2-nitrotoluene.

(CH3C6H4)2N2H2 → (C6H3(CH3)NH2)2

Uses

2-Tolidine aromatic amine is used mainly for dye production. 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 is also used for the production of certain elastomers.

Orthotolidine in chlorine test kit

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.

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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