CAS 852445-81-9 Chloro[1,3-bis(2,4,6-trimethylphenyl)2H-imidazol-2-ylidene]gold(I), 98%

Synonyms

1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene gold(I) chloride; Chloro[1,3-Bis(Mesityl)Imidazole-2-Ylidene]Gold(I); Chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]gold(I); C21H24AuClN2; Chloro[1,3-bis(2,4,6-trimethylphenyl)2H-imidazol-2-ylidene]gold(I); AuCl(IMes); Chloro(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)aurate(I); 3213AC;

IUPAC Name

[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]-chlorogold;

Molecular Weight

536.854g/mol

Molecular Formula

C21H24AuClN2;

Canonical SMILES

CC1=CC(=C(C(=C1)C)N2C=CN(C2=[Au]Cl)C3=C(C=C(C=C3C)C)C)C;

InChI

InChI=1S/C21H24N2.Au.ClH/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;;1H/q;+1;/p-1;

InChI Key

YFUIKJIITPMUAT-UHFFFAOYSA-M;

Complexity

468

Covalently-Bonded Unit Count

Exact Mass

536.129g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

536.129g/mol

Rotatable Bond Count

Topological Polar Surface Area

6.5A^2

Application

Chloro[1,3-bis(2,4,6-trimethylphenyl)2H-imidazol-2-ylidene]gold(I), 98%, is a versatile organometallic catalyst known as [(IMes)AuCl]. It serves multiple functions across various industries due to its effectiveness in catalyzing complex chemical transformations. This organometallic compound plays a crucial role in industrial chemistry, pharmaceuticals, and materials science, with specific applications including the rearrangement of alkynyl sulfoxides to benzothiepinones and the transformation of homopropargylic ethers into α,β-unsaturated carbonyl compounds. Moreover, it is influential in oxidative cyclopropanation of N-allylynamides, yielding 3-aza-bicyclo[3.1.0]-hexan-2-one derivatives, and in facilitating the oxidative rearrangement of homopropargylic ethers to cyclobutanones. This white powder reflects the ongoing 'Gold Rush' in catalysis by offering efficient pathways for the synthesis of complex molecules.

March 29, 2025

Exceptional Catalyst for Advanced Research

Using Chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]gold(I) as a catalyst significantly enhanced our lab's synthesis of benzothiepinones. This high-quality reagent streamlined our processes in organometallic applications, making complex transformations efficient. Highly recommend for any advanced chemical research.