2,6-Xylidine

Source: Wikipedia, the free encyclopedia.
2,6-Xylidine
Names
Preferred IUPAC name
2,6-Dimethylaniline
Other names
  • 2,6-Dimethylbenzene-1-amine
  • 2,6-Dimethylbenzenamine
  • 2,6-Dimethylphenylamine
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.001.599 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 checkY
    Key: UFFBMTHBGFGIHF-UHFFFAOYSA-N checkY
  • InChI=1/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3
    Key: UFFBMTHBGFGIHF-UHFFFAOYAI
  • Nc1c(cccc1C)C
Properties
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)
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 checkY☒N ?)

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.[1]

Production, occurrence, reactions

Many xylidines are prepared by nitration of a xylene followed by

related xylenol with ammonia in the presence of oxide catalysts.[1]

2,6-Xylidine is also a major metabolite of the drug xylazine in both horses,[2] and humans.[3]

2,6-Xylidine is the precursor to the

NHC ligand called Xyl.[4]

Uses

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

References

  1. ^
    ISBN 9783527303854
    .
  2. PMID 15030885
    – via PubMed.
  3. ^ Drug & Chemical Evaluation Section (February 2021). Xylazine (PDF). Diversion Control Division (Report). Drug Enforcement Administration. DEA PRB # 2021-15. Retrieved 2022-11-15.
  4. doi:10.1021/ed300243s
    .
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