2,5-Xylidine

2,5-Xylidine
Names
Preferred IUPAC name
2,5-Dimethylaniline
Other names
2,5-Dimethylphenylamine, 2,5-Dimethylbenzenamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.229 Edit this at Wikidata
UNII
  • InChI=1S/C8H11N/c1-6-3-4-7(2)8(9)5-6/h3-5H,9H2,1-2H3 ☒N
    Key: VOWZNBNDMFLQGM-UHFFFAOYSA-N ☒N
  • Cc1ccc(C)c(N)c1
Properties
C8H11N
Melting point 6 °C (43 °F; 279 K)
Boiling point 218 °C (424 °F; 491 K)
Hazards
Flash point 97
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,5-Xylidine is an organic compound with the formula C6H3(CH3)2NH2. It is one of several isomeric xylidines. It is a colorless viscous liquid. Commercially significant derivatives include Solvent Yellow 30, Solvent Red 22, Acid Red 65, and Solvent Red 26.[1]

Solvent Red 26 is a commercial dye prepared from 2,5-xylidine

Production

Like many xylidines, it is prepared by nitration of the corresponding xylene followed by reduction of the nitroxylene. Reduction can be effected with HCl/Fe, but usually is achieved by catalytic hydrogenation:

Me2C6H4 + HNO3 → Me2C6H3NO2 + H2O
Me2C6H3NO2 + 3 H2 → Me2C6H3NH2 + 3H2O

Safety

It is mutagenic and tumor-inducing. Acute toxicity of xylidines is modest as indicated by LD50 (rats, oral) are in the range 0.1-1 g/kg.

References

  1. ^ M. Meyer (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 9783527303854.