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

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

CAS No.: 141556-45-8

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

Synonyms: IMes.HCl;IMESCL;1,3-Bis(mesityl)imidazolium chloride;1,3-DiMesityl-1H-iMidazol-3-iuM chloride;1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE;1,3-DIMESITYLIMIDAZOLIUM CHLORIDE;1H-Imidazolium, 1,3-bis(2,4,6-trimethylphenyl)-, chloride (1:1);1,3-Bisimidazolium chloride;1,3-DimesitylimidazoliumChloride>1,3-Dimesitylimidazoliumchloride,96%

CBNumber:: CB5707153

Molecular Formula:: C21H25ClN2

Molecular Weight:: 340.89

MDL Number:: MFCD02684541

MOL File:: 141556-45-8.mol

MSDS File:: SDS

TDS File:: TDS

Last updated:2026-07-26 20:01:20

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1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride 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
pka	19.40(Temp: 25 °C; Solvent: Dimethyl sulfoxide)
color	Off-white to beige
Water Solubility	Slightly soluble in water.
InChI	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
InChIKey	OTOSIXGMLYKKOW-UHFFFAOYSA-M
SMILES	N1(C=C[N+](C2C(C)=CC(C)=CC=2C)=C1)C1C(C)=CC(C)=CC=1C.[Cl-]
CAS DataBase Reference	141556-45-8(CAS DataBase Reference)
UNSPSC Code	12352005
NACRES	NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P261-P264-P271-P280-P302+P352-P305+P351+P338

target organs

Respiratory system

PPE

dust mask type N95 (US), Eyeshields, Gloves

Hazard Codes

Risk Statements

36/37/38

Safety Statements

26-36

WGK Germany

TSCA

HS Code

29332900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

NFPA 704

	1
2		0

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride price More Price(65)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	574066	1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride	141556-45-8	1g	$95.2	2026-04-30	Buy
Sigma-Aldrich	574066	1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride	141556-45-8	5g	$290	2026-04-30	Buy
TCI Chemical	D3446	1,3-Dimesitylimidazolium Chloride >98.0%(HPLC)	141556-45-8	1g	$68	2026-04-30	Buy
TCI Chemical	D3446	1,3-Dimesitylimidazolium Chloride >98.0%(HPLC)	141556-45-8	5g	$217	2026-04-30	Buy
Strem Chemicals	07-0299	1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride, min. 97% min.97%	141556-45-8	1g	$69	2026-04-30	Buy

Product number	Packaging	Price	Buy
574066	1g	$95.2	Buy
574066	5g	$290	Buy
D3446	1g	$68	Buy
D3446	5g	$217	Buy
07-0299	1g	$69	Buy

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

reaction suitability

reagent type: ligand

Synthesis

N,N'-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine

56222-36-7

3188-13-4

141556-45-8

The general procedure for the synthesis of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride from N,N'-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine and chloromethyl ethyl ether is as follows: in a dry flask, N,N'-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine (3 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran ( 25 ml) followed by slow dropwise addition of chloromethyl ethyl ether (1.04 g, 11 mmol). The reaction mixture was stirred at 40 °C for 18 h under nitrogen protection. After completion of the reaction, ether (25 ml) was added to precipitate a white solid. The solid product was collected by filtration and washed with ether and finally dried under vacuum to afford 1,3-bis(2,4,6-trimethylphenyl)imidazole chloride (IMes-HCl) 2.2 g in 65% yield. The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz) and 13C NMR (CDCl3, 100 MHz): 1H NMR δ 2.15 (s, 12H), 2.33 (s, 6H), 7.00 (s, 4H), 7.70 (s, 2H), 10.73 (s, 1H); 13C NMR δ 17.6, 21.1, 124.8, 129.8, 130.7, 134.1, 139.2, 141.1.

References

[1] Journal of Organic Chemistry, 2008, vol. 73, # 7, p. 2784 - 2791
[2] Tetrahedron Letters, 2012, vol. 53, # 7, p. 815 - 818
[3] Tetrahedron, 2012, vol. 68, # 38, p. 7949 - 7955
[4] Chemical Communications, 2011, vol. 47, # 5, p. 1559 - 1561
[5] Journal of Organometallic Chemistry, 2013, vol. 743, p. 44 - 48

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

Synthesis of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride from Formaldehyde and N,N'-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Preparation Products And Raw materials

Raw materials

Formaldehyde N,N'-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine Chloromethyl ethyl ether

Preparation Products

1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene RutheniuM, dichloro[1,3-dihydro-1,3-bis(2,4,6-triMethylphenyl)-2H-iMidazol-2-ylidene](phenylMethylene)(tricyclohexylphosphine)-, (SP-5-41)- 1,3-Bis(2,4,6-trimethylphenyl)imidazolium bicarbonate

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

Global( 271)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Shandong Puchuang Pharmaceutical Technology Co., Ltd.	18953403321	3218803372@qq.com	China	283	58
Shaanxi Rock New Materials Co., Ltd.	0917-8888777 18691786767	liuwei@bjrock.com	China	309	62
J & K SCIENTIFIC LTD.	18210857532 18210857532	jkinfo@jkchemical.com	China	96815	76
Meryer (Shanghai) Chemical Technology Co., Ltd.	4006356688 18621169109	market03@meryer.com	China	40202	62
Alfa Aesar	400-6106006	saleschina@alfa-asia.com	China	30103	84
TCI (Shanghai) Development Co., Ltd.	021-67121386	Sales-CN@TCIchemicals.com	China	24512	81
ShangHai DEMO Chemical Co.,Ltd	400-021-7337 2355568890	sales@demochem.com	China	2569	57
Ark Pharm, Inc.	847-367-3680	sales@arkpharminc.com	United States	1669	56
Beijing HwrkChemical Technology Co., Ltd	89508211 18501085097	sales.bj@hwrkchemical.com	China	9407	55
Energy Chemical	400-0056266	sales8178@energy-chemical.com	China	44850	61

Supplier	Advantage
Shandong Puchuang Pharmaceutical Technology Co., Ltd.	58
Shaanxi Rock New Materials Co., Ltd.	62
J & K SCIENTIFIC LTD.	76
Meryer (Shanghai) Chemical Technology Co., Ltd.	62
Alfa Aesar	84
TCI (Shanghai) Development Co., Ltd.	81
ShangHai DEMO Chemical Co.,Ltd	57
Ark Pharm, Inc.	56
Beijing HwrkChemical Technology Co., Ltd	55
Energy Chemical	61

View Lastest Price from 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2025-04-04	1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride 141556-45-8		1KG	98%	1Ton	Henan Aochuang Chemical Co.,Ltd.
2022-09-27	1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8		1kg	99%	1000kg	henan kanbei chemical co.,ltd
2021-07-02	1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8	$10.00-15.00	1KG	99%+ HPLC		Zhuozhou Wenxi import and Export Co., Ltd

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
141556-45-8
98%
Henan Aochuang Chemical Co.,Ltd.

1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
141556-45-8
$0.00
99%
henan kanbei chemical co.,ltd

1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
141556-45-8
$10.00-15.00
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

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

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

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

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1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 1,3-(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE N,N'-(2,4,6-TRIMETHYLPHENYL)DIHYDROIMADAZOLIUM CHLORIDE 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLI& 1,3-Bis(2,4,6-trimethylphenyl)imidazoliumchloride,min.95% 1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-1H-IMIDAZOLIUM CHLORIDE 1,3-Bisimidazolium chloride 1,3-Bis-(2,4,6-trimethyl-phenyl)-3H-imidazol-1-ium chloride 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride, min. 97% 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride,95% 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride,97% [1,3-bis(2,4,6-triMethylphenyl)-3H-1$l^{5},3-iMidazol-1-yliuM-2-yl]chloranuide 1,3-Bis(2,4,6-triMethylphenyl)iMidazoliuMchloride,Min.97% 1,3-Bis(2,4,6-trimethylphenyl)imidazolium Chloride IMes.HCl 1,3-bis(2,4,6-triMethylphenyl)iMidazol-1-iuM,chloride 1,3-Dimesitylimidazoliumchloride,96% 1,3-Dihydro-1,3-dimesityl-2H-imidazol-2-ylidene monohydrochloride 1,3-Bis(2,4,6-trimethyphenyl)imidazolium chloride 1,3-bis(2,4,6-trimethylphenyl)imidazol-1-ium 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-1-ium 1,3-DimesitylimidazoliumChloride> 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chlori... TIANFU CHEM 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 1,3-bis(2,4,6-trimethylphenyl)-1H-Imidazolium chloride (1:1) 1,3-bis (2,4,6-trimethylphenyl) imidazole chloride 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride,98% 1,3-Dimesityl-1H-imidazol-3-ium chloride , IMes.HCl 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE 1,3-Bis(mesityl)imidazolium chloride 1,3-DIMESITYLIMIDAZOLIUM CHLORIDE 1,3-DiMesityl-1H-iMidazol-3-iuM chloride 1H-Imidazolium, 1,3-bis(2,4,6-trimethylphenyl)-, chloride (1:1) IMes.HCl IMESCL 141556-45-8 C21H25N2Cl C21H25ClN2 NHC Compounds Catalysis and Inorganic Chemistry organic amine Imidazolium Compounds Ligands N-Heterocyclic Carbene Ligands Synthetic Organic Chemistry Catalysis and Inorganic Chemistry Chemical Synthesis NHC Compounds API intermediates Achiral Nitrogen NHC