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
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).

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 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.[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[5] and the herbicide metazachlor [de].[6]

Synthesis of metazachlor

References

  1. ^ a b M. Meyer (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 9783527303854.
  2. ^ Spyridaki, M.-H.; Lyris, E.; Georgoulakis, I.; Kouretas, D.; Konstantinidou, M.; Georgakopoulos, C. G. (2004-04-01). "Determination of xylazine and its metabolites by GC-MS in equine urine for doping analysis". Journal of Pharmaceutical and Biomedical Analysis. 35 (1): 107–116. doi:10.1016/j.jpba.2003.12.007. ISSN 0731-7085. 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. ^ Ison, Elon A.; Ison, Ana (2012). "Synthesis of Well-Defined CopperN-Heterocyclic Carbene Complexes and Their Use as Catalysts for a "Click Reaction": A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry". Journal of Chemical Education. 89 (12): 1575. Bibcode:2012JChEd..89.1575I. doi:10.1021/ed300243s.
  5. ^ Blaser, Hans-Ulrich; Spindler, Felix (1997). "Enantioselective catalysis for agrochemicals. The case histories of (S)–metolachlor, (R)–metalaxyl and clozylacon". Topics in Catalysis. 4 (3/4): 275–282. doi:10.1023/A:1019164928084.
  6. ^ Unger, Thomas A. (1996-12-31). Pesticide Synthesis Handbook. William Andrew. p. 35. ISBN 0-8155-1853-6.