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HomeProduct name list1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

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

Synonym(s):1,3-Bis(mesityl)imidazolium chloride;1,3-Dihydro-1,3-dimesityl-2H-imidazol-2-ylidene monohydrochloride;1,3-Dimesitylimidazolium chloride

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

What is 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride ?

Chemical properties

off-white to beige powder

The Uses of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

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.

What are the applications of Application

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride is a ligand for arylation of aldehydes

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.
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.
Reaction of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
Reaction of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
Reaction of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

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

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.
CAS DataBase Reference 141556-45-8(CAS DataBase Reference)

Safety information for 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

InChIKey OTOSIXGMLYKKOW-UHFFFAOYSA-M

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