CAS 250285-32-6 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Synonyms

IPr·HCl

IUPAC Name

1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium;chloride

Molecular Weight

425.05

Molecular Formula

C27H37ClN2

Canonical SMILES

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

InChI

AVJBQMXODCVJCJ-UHFFFAOYSA-M

InChI Key

InChI=1S/C27H37N2.ClH/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;/h9-21H,1-8H3;1H/q+1;/p-1

Melting Point

278 °C(dec.)(lit.)

Purity

98%+

Appearance

Solid

Complexity

421

Covalently-Bonded Unit Count

Exact Mass

424.265g/mol

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

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

Monoisotopic Mass

424.265g/mol

Rotatable Bond Count

Topological Polar Surface Area

8.8A^2

Application

1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride is primarily utilized in organic synthesis and as a pharmaceutical intermediate. This compound, which appears as a white to light orange powder or crystal and is soluble in methanol, serves multiple roles in chemical reactions. It acts as a reagent in the synthesis of NHC Copper(I) complexes with dipyridylamine ligands, which are noteworthy for their luminescent properties and potential use in organic light-emitting diode applications. Furthermore, it's involved in the creation of 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic Acid Methyl Ester, a derivative of the drug Vadimezan. This compound also serves as a precursor to various metal catalysts: Pd catalysts for C-N and C-C coupling reactions, Ni catalysts for C-N coupling reactions, and Cu catalysts for copper hydride reactions. Additionally, it functions as a ligand in double carbonylation reactions and Ru-catalyzed carbonylative C-H cyclization of 2-aryl phenols. Notably, it demonstrates activity against all stages of Trypanosoma Cruzi, offering potential as a treatment for Chagas disease.

January 26, 2025

A Versatile Reagent for Advanced Organic Synthesis

Using Alfa Chemistry's 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride in our synthesis lab was seamless. Its versatility as a ligand greatly enhanced our C-N coupling reactions, proving indispensable for our research into organic light-emitting diode applications.