2,5-Xylidine

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.

2,5-Xylidine

Names
Preferred IUPAC name 2,5-Dimethylaniline
Other names 2,5-Dimethylphenylamine, 2,5-Dimethylbenzenamine
Identifiers
CAS Number	95-78-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:518305 N
ChEMBL	ChEMBL249120 N
ChemSpider	6989 Y
DrugBank	DB02163 Y
ECHA InfoCard	100.002.229
PubChem CID	7259
UNII	XWK0W8DA04 Y
CompTox Dashboard (EPA)	DTXSID3026306
InChI InChI=1S/C8H11N/c1-6-3-4-7(2)8(9)5-6/h3-5H,9H2,1-2H3 N Key: VOWZNBNDMFLQGM-UHFFFAOYSA-N N
SMILES Cc1ccc(C)c(N)c1
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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.