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696188

Sigma-Aldrich

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

97%

Synonym(s):
1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene
Empirical Formula (Hill Notation):
C21H24N2
CAS Number:
Molecular Weight:
304.43
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

powder

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

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

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Sol. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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