2,6-Xylidine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
2,6-Xylidine
2,6-Xylidin.svg
Names
IUPAC name
2,6-Dimethylaniline
Other names
  • 2,6-Dimethylbenzene-1-amine
  • 2,6-Dimethylbenzenamine
  • 2,6-Dimethylphenylamine
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.599
KEGG
Properties
C8H11N
Molar mass 121.18 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 YesYN ?)
Infobox references

2,6-Xylidine is an aniline derivative with the chemical formula (CH3)2C6H3NH2. It is an isomer of 2,4-xylidine and 3,4-xylidine. It is a colourless liquid although commercial samples can appear to be yellow or even red.

Production and reactions[edit]

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]

Other[edit]

2,6-Xylidine is the precursor to the NHC ligand called Imes.[2]

References[edit]

  1. ^ M. Meyer "Xylidines" in Ullmann's Encylclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a28_455
  2. ^ 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.