CAS 141556-45-8 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

Synonyms

1,3-Dimesityl-1H-Imidazol-3-Ium Chloride; 1,3-Dimesitylimidazolium Chloride

IUPAC Name

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

Molecular Weight

340.89

Molecular Formula

C21H25ClN2

Canonical SMILES

CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-];

InChI

OTOSIXGMLYKKOW-UHFFFAOYSA-M

InChI Key

InChI=1S/C21H25N2.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;/h7-13H,1-6H3;1H/q+1;/p-1

Melting Point

>300 °C-lit.

Purity

98%

Solubility

Soluble in methanol,slightly soluble in water.

Appearance

Off-white to yellow powder

Storage

room temperature

Complexity

335

Covalently-Bonded Unit Count

Exact Mass

340.171g/mol

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-]

Monoisotopic Mass

340.171g/mol

Rotatable Bond Count

Topological Polar Surface Area

8.8A^2

Application

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride, an off-white to beige powder, serves as a versatile phosphine-free ligand in a variety of metal-catalyzed coupling reactions. This compound is particularly effective in facilitating challenging reactions, such as the palladium-catalyzed cross-coupling of aryl Grignards with aryl chlorides, known as the Kumada reaction. Additionally, it finds application in Suzuki coupling reactions, where it aids the union of arylboronic acids with less reactive aryl chlorides by acting as a precursor to a nucleophilic carbene. This carbene functions as a bulky, electron-rich "phosphine mimic," crucial for several metal-catalyzed reactions. Its utility extends to palladium-catalyzed aryl chloride Suzuki cross-coupling, ruthenium-carbene catalysts for ring-closing metathesis, and the Sonogashira coupling of aryl bromides. Moreover, it serves as a ligand for arylation of aldehydes and carbene-catalyzed intermolecular arylation of C-H bonds, as well as a catalyst for boron conjugate additions to α,β-unsaturated carbonyls. It is also employed in dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes and as a precursor for carbene in the conjugate silylation of such carbonyls.

January 5, 2025

Essential Ligand for Challenging Couplings

I've used Alfa Chemistry's 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride in Pd-catalyzed Suzuki reactions. This off-white powder enhanced yields in aryl chloride couplings, making it a go-to for complex transformations in my lab.