CAS 141556-42-5 1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, min. 98%

Synonyms

IMes; 141556-42-5; D3870; C-1996; 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE; 6880AA; SC11699; 1,3-Dimesitylimidazol-2-ylidene; AK119064; 1,3-bis(2,4,6-trimethylphenyl)-imidazolium;

IUPAC Name

1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-1-ium-2-ide;

Molecular Weight

304.437g/mol

Molecular Formula

C21H24N2;

Canonical SMILES

CC1=CC(=C(C(=C1)C)N2C=C[N+](=[C-]2)C3=C(C=C(C=C3C)C)C)C;

InChI

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;

Complexity

414

Covalently-Bonded Unit Count

Exact Mass

304.194g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

304.194g/mol

Rotatable Bond Count

Topological Polar Surface Area

6.2A^2

Application

1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, min. 98%, serves as a highly effective nucleophilic N-heterocyclic carbene (NHC) ligand. Its primary purpose is to facilitate the synthesis of various metal complexes that act as catalysts in key chemical reactions. Specifically, it enables the creation of a rhodium complex for the selective hydrogenation of substituted aryl and heteroaryl boronate esters into cis-substituted borylated cycloalkanes. Additionally, this product is utilized in forming a ruthenium complex, which acts as a catalyst in olefin ring-closing metathesis reactions, demonstrating enhanced reactivity. It also plays a crucial role as an ancillary ligand in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, particularly between aryl chlorides or aryl triflates and arylboronic acids. This nucleophilic carbene serves as a bulky, electron-rich "phosphine mimic," optimizing performance in metal-catalyzed reactions.

February 21, 2025

Essential Catalyst for Enhanced Reactions

IMes dramatically improved our Pd-catalyzed Suzuki-Miyaura and olefin metathesis reactions, showing exceptional stability and activity. It's an indispensable ligand for precise and efficient synthesis in our research projects. Highly recommend for reliable results.