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  • 696188 - 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene

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696188 Sigma-Aldrich

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene

97%

Synonym: 1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene

  • CAS Number 141556-42-5

  • Empirical Formula (Hill Notation) C21H24N2

  • Molecular Weight 304.43

  •  MDL number MFCD09265338

  •  PubChem Substance ID 329761806

  •  NACRES NA.22

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Properties

Related Categories Carbon-Donor Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, NHC Compounds
Quality Level   100
assay   97%
reaction suitability   reagent type: catalyst
mp   140 °C
storage temp.   −20°C
SMILES string   Cc1cc(C)c(N2[C]N(C=C2)c3c(C)cc(C)cc3C)c(C)c1
InChI   1S/C21H24N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h7-12H,1-6H3
InChI key   JCYWCSGERIELPG-UHFFFAOYSA-N

Description

Application

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene (IMes) is a nucleophilic N-heterocyclic carbene (NHC) ligand.
It can be used to synthesize:
• IMes ligated-rhodium complex as a catalyst for the selective hydrogenation of substituted aryl and heteroaryl boronate esters to cis-substituted borylated cycloalkanes.
• IMes/ruthenium complex (Cp*Ru(IMes)Cl)(Cp* =η5-C5Me3) as a catalyst for olefin ring closing metathesis reaction.


IMes is also used as an ancillary ligand in Pd-catalyzed Suzuki-Miyaura cross-coupling reaction between aryl chlorides or aryl triflates and arylboronic acids.

Packaging

1 g in glass bottle

250 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
UN1325 - class 4.1 - PG 3 - Flammable solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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