2,6-Xylidine

2,6-Xylidine

Names
Preferred IUPAC name 2,6-Dimethylaniline
Other names 2,6-Dimethylbenzene-1-amine 2,6-Dimethylbenzenamine 2,6-Dimethylphenylamine
Identifiers
CAS Number	87-62-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28738 Y
ChemSpider	6630 Y
ECHA InfoCard	100.001.599
KEGG	C11004 Y
PubChem CID	6896
UNII	4FT62OX08D Y
CompTox Dashboard (EPA)	DTXSID8026307
InChI InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 Y Key: UFFBMTHBGFGIHF-UHFFFAOYSA-N Y InChI=1/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 Key: UFFBMTHBGFGIHF-UHFFFAOYAI
SMILES Nc1c(cccc1C)C
Properties
Chemical formula	C8H11N
Molar mass	121.183 g·mol−1
Appearance	Colorless liquid
Density	0.9842 g/mL
Melting point	11.45 °C (52.61 °F; 284.60 K)
Boiling point	215 °C (419 °F; 488 K)
Refractive index (nD)	1.5601
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

2,6-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 are the anesthetics lidocaine, bupivacaine, mepivacaine, and etidocaine.

Production, occurrence, reactions

Many xylidines are prepared by nitration of a xylene followed by hydrogenation of the nitroaromatic, but this approach is not efficient for this isomer. Instead, it is prepared from by treatment of the related xylenol with ammonia in the presence of oxide catalysts.

2,6-Xylidine is also a major metabolite of the drug xylazine in both horses, and humans.

2,6-Xylidine is the precursor to the NHC ligand called Xyl.

Uses

2,6-Xylidine is a precursor to the fungicide Metalaxyl and the herbicide metazachlor.