696188

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: 141556-42-5
• Molecular Weight: 304.43
• MDL number: MFCD09265338
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761806
• NACRES: NA.22

Properties

• Quality Level: 100
• 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

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.

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Warning
• Hazard Statements: H228,H315,H319,H335
• Precautionary Statements: P210 - P302 + P352 - P305 + P351 + P338
• 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