1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

499.2°C (rough estimate)

Density 

1.0279 (rough estimate)

refractive index 

1.5940 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Powder

color 

Off-white to beige

Water Solubility 

Slightly soluble in water.

InChIKey

OTOSIXGMLYKKOW-UHFFFAOYSA-M

CAS DataBase Reference

141556-45-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

No

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Usage And Synthesis

Chemical Properties

off-white to beige powder

Uses

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides.

Preparation

In a flask, the imine(3 g, 10 mmol) was dissolved in tetrahydrofuran(25 ml), followed by dropwise addition of chloromethyl ethyl ether(1.04 g, 11 mmol). the mixture was stirred under N2 at 40 °C for 18 h, and then ethyl ether(25 ml) was added to separate white solid. The solid was filtered and washed with ethyl ether. Finally, the white solid was dried under vacuum affording 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride.

Reactions

Precursor to the nucleophilic carbene that serves as a bulky, electron-rich "phosphine mimic" for metal-catalyzed reactions.
(a) Palladium-catalyzed Suzuki cross-coupling of aryl chlorides.
(b) Palladium-catalyzed Kumada cross-coupling of aryl chlorides.
(c) Ruthenium-carbene catalysts for ring-closing metathesis.
(d) Suzuki coupling of aryltrimethylammonium salts.
(e) Sonogashira coupling of aryl bromides.
Precursor to a nucleophilic carbene that serves as catalyst.
Ligand for arylation of aldehydes.
Ligand for carbene catalyzed intermolecular arylation of C-H bonds.
Catalyst for boron conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls.
Ligand for dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes.
Precursor for carbene for conjugate silylation of alpha, beta-unsaturated carbonyls.

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

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