1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
- Product Name
- 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
- CAS No.
- 141556-45-8
- Chemical Name
- 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
- Synonyms
- IMes.HCl;IMESCL;1,3-DiMesityl-1H-iMidazol-3-iuM chloride;1,3-Bis(mesityl)imidazolium chloride;1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE;1,3-Bisimidazolium chloride;1,3-DIMESITYLIMIDAZOLIUM CHLORIDE;1,3-DimesitylimidazoliumChloride>1,3-Dimesitylimidazoliumchloride,96%;1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLI&
- CBNumber
- CB5707153
- Molecular Formula
- C21H25ClN2
- Formula Weight
- 340.89
- MOL File
- 141556-45-8.mol
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 574066
- Product name
- 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
- Packaging
- 1g
- Price
- $86.7
- Updated
- 2024/03/01
- Product number
- 574066
- Product name
- 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
- Packaging
- 5g
- Price
- $264
- Updated
- 2024/03/01
- Product number
- D3446
- Product name
- 1,3-Dimesitylimidazolium Chloride
- Purity
- >98.0%(HPLC)
- Packaging
- 1g
- Price
- $71
- Updated
- 2024/03/01
- Product number
- D3446
- Product name
- 1,3-Dimesitylimidazolium Chloride
- Purity
- >98.0%(HPLC)
- Packaging
- 5g
- Price
- $228
- Updated
- 2024/03/01
- Product number
- H27535
- Product name
- 1,3-Dimesitylimidazolium chloride, 96%
- Packaging
- 1g
- Price
- $73.65
- Updated
- 2024/03/01
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Chemical Properties,Usage,Production
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 Preparation Products And Raw materials
Raw materials
Preparation Products
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Suppliers
View Lastest Price from 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride manufacturers
- Product
- 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2022-09-26
- Product
- 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-06-27
- Product
- 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8
- Price
- US $3.00/Kg/Bag
- Min. Order
- 25Kg/Bag
- Purity
- 99%
- Supply Ability
- 20 Tons
- Release date
- 2020-11-10