glyoxal-bis(mesitylimine)

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| ImageFile = Glyoxal-bis(mesitylimine).svg

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| IUPACName = 2,4,6-Trimethyl-N-[(2E)-2-[(2,4,6-trimethylphenyl)imino]ethylidene]aniline

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|Section1={{Chembox Identifiers

| CASNo = 647032-09-5

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| CASNo1 = 56222-36-7

| CASNo1_Comment = (non-specific)

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| UNII =SC7SFP5T49

| SMILES = CC1=CC(C)=C(\N=C\C=N\C2=C(C)C=C(C)C=C2C)C(C)=C1

| PubChem = 3741651

| ChemSpiderID = 2971578

| StdInChI = 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+

| StdInChIKey = YVKAJRYLHIECOK-KVJLFNRQSA-N

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|Section2={{Chembox Properties

| C=20 | H=24 | N=2

| Appearance = Yellow solid

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|Section3={{Chembox Hazards

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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.{{cite journal | doi = 10.1021/ed300243s | title = 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 | year = 2012 | last1 = Ison | first1 = Elon A. | last2 = Ison | first2 = Ana | journal = Journal of Chemical Education | volume = 89 | issue = 12 | pages = 1575–1577| bibcode = 2012JChEd..89.1575I }}{{cite journal |doi=10.1021/ed085p1646|title=Preparation of a N-Heterocyclic Carbene Nickel(II) Complex. Synthetic Experiments in Current Organic and Organometallic Chemistry

|first1=Vincent|last1=Ritleng|first2=Eric|last2=Brenne|first3=Michael J.|last3=Chetcuti|journal=J. Chem. Educ.|year=2008|volume=85|page=1646}}

Related compounds

File:(iPr2C6H3N=CHCH=N(C6H3iPr2).jpg

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

{{cite journal|title=Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix|first1=Junting|last1=Chen|first2=Tobias|last2=Ritter|journal=Org. Synth. |year=2019|volume=96|page=16|doi=10.15227/orgsyn.096.0016|doi-access=free}}

References