Glyoxal-bis(mesitylimine)

Glyoxal-bis(mesitylimine)
Names
	IUPAC name 2,4,6-Trimethyl-N-[(2E)-2-[(2,4,6-trimethylphenyl)imino]ethylidene]aniline
Identifiers
CAS Number	647032-09-5; 56222-36-7 (non-specific) ;
3D model (JSmol)	Interactive image;
ChemSpider	2971578;
PubChem CID	3741651;
UNII	SC7SFP5T49 ;
CompTox Dashboard (EPA)	DTXSID00395802 ;
	InChI 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;
	SMILES CC1=CC(C)=C(\N=C\C=N\C2=C(C)C=C(C)C=C2C)C(C)=C1;
Properties
Chemical formula	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

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]

Related compounds

Sample of alpha-diimine derived from 2,6-diisopropylaniline and glyoxal.

Glyoxal-bis(triisopropylphenylimine), which is bulkier than glyoxal-bis(mesitylimine).

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^ 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.
^ Chen, Junting; Ritter, Tobias (2019). "Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix". Org. Synth. 96: 16. doi:10.15227/orgsyn.096.0016.