Tolidine

2-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
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:
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).
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Infobox references

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.

(CH3C6H4)2N2H2 → (C6H3(CH3)NH2)2
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