2,6-Xylidine Explained

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.

References

  1. Encyclopedia: M. Meyer. Xylidines. Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. Weinheim. 2012. 10.1002/14356007.a28_455. 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 . 10.1016/j.jpba.2003.12.007 . 0731-7085 . 15030885 . PubMed.
  3. Xylazine . February 2021 . Drug Enforcement Administration . Diversion Control Division. Drug & Chemical Evaluation Section. DEA PRB # 2021-15 . 2022-11-15 .
  4. 10.1021/ed300243s. 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. 2012. Ison. Elon A.. Ison. Ana. 2012JChEd..89.1575I.
  5. 10.1023/A:1019164928084 . 1997 . Blaser . Hans-Ulrich . Spindler . Felix . Enantioselective catalysis for agrochemicals. The case histories of (S)–metolachlor, (R)–metalaxyl and clozylacon . Topics in Catalysis . 4 . 3/4 . 275–282 .

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