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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
  • 647032-09-5
  • 56222-36-7 (non-specific) Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2971578
  • 3741651
UNII
  • SC7SFP5T49 Y
  • DTXSID00395802
  • 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).

Related compounds edit

 
Sample of alpha-diimine derived from 2,6-diisopropylaniline and glyoxal.
  • Glyoxal-bis(triisopropylphenylimine), which is bulkier than glyoxal-bis(mesitylimine).

[3]

References edit

  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.

glyoxal, mesitylimine, organic, compound, with, formula, h2c2, nc6h2me3, methyl, yellow, solid, that, soluble, organic, solvents, classified, diimine, ligand, used, coordination, chemistry, homogeneous, catalysis, synthesized, condensation, trimethylaniline, g. 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 CAS Number 647032 09 556222 36 7 non specific Y 3D model JSmol Interactive image ChemSpider 2971578 PubChem CID 3741651 UNII SC7SFP5T49 Y 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 C 20H 24N 2 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 referencesRelated compounds edit nbsp Sample of alpha diimine derived from 2 6 diisopropylaniline and glyoxal Glyoxal bis triisopropylphenylimine which is bulkier than glyoxal bis mesitylimine 3 References edit 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 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 Retrieved from https en wikipedia org w index php title Glyoxal bis mesitylimine amp oldid 1105344938, wikipedia, wiki, book, books, library,

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