Glyoxal-bis(mesitylimine)

Glyoxal-bis(mesitylimine) is an organic compound with the formula H2C2(NC6H2Me3)2 (Me = methyl). It is a yellow solid that is soluble in organic solvents. It is classified as a diimine ligand. It is used in coordination chemistry and homogeneous catalysis. It is synthesized by condensation of 2,4,6-trimethylaniline and glyoxal. In addition to its direct use as a ligand, it is a precursor to imidazole precursors to the popular NHC ligand called IMes.[1][2]

Glyoxal-bis(mesitylimine)
Names
IUPAC name
2,4,6-Trimethyl-N-[(2E)-2-[(2,4,6-trimethylphenyl)imino]ethylidene]aniline
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C20H24N2/c1-13-9-15(3)19(16(4)10-13)21-7-8-22-20-17(5)11-14(2)12-18(20)6/h7-12H,1-6H3/b21-7+,22-8+
    Key: YVKAJRYLHIECOK-KVJLFNRQSA-N
  • CC1=CC(C)=C(\N=C\C=N\C2=C(C)C=C(C)C=C2C)C(C)=C1
Properties
C20H24N2
Molar mass 292.426 g·mol−1
Appearance Yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Sample of alpha-diimine derived from 2,6-diisopropylaniline and glyoxal.
  • Glyoxal-bis(triisopropylphenylimine), which is bulkier than glyoxal-bis(mesitylimine).

[3]

References
  1. 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): 1575–1577. Bibcode:2012JChEd..89.1575I. doi:10.1021/ed300243s.
  2. Ritleng, Vincent; Brenne, Eric; Chetcuti, Michael J. (2008). "Preparation of a N-Heterocyclic Carbene Nickel(II) Complex. Synthetic Experiments in Current Organic and Organometallic Chemistry". J. Chem. Educ. 85: 1646. doi:10.1021/ed085p1646.
  3. Chen, Junting; Ritter, Tobias (2019). "Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix". Org. Synth. 96: 16. doi:10.15227/orgsyn.096.0016.
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