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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-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

Molecular Weight:: 340.89

MDL Number:: MFCD02684541

MOL File:: 141556-45-8.mol

MSDS File:: SDS

Last updated:2025-07-24 18:13:45

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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
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

Hazard Codes

Risk Statements

36/37/38

Safety Statements

26-36

WGK Germany

TSCA

HS Code

29332900

NFPA 704

	1
2		0

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride price More Price(41)

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	$89.4	2025-07-31	Buy
Sigma-Aldrich	574066	1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride	141556-45-8	5g	$272	2025-07-31	Buy
TCI Chemical	D3446	1,3-Dimesitylimidazolium Chloride >98.0%(HPLC)	141556-45-8	1g	$68	2025-07-31	Buy
TCI Chemical	D3446	1,3-Dimesitylimidazolium Chloride >98.0%(HPLC)	141556-45-8	5g	$217	2025-07-31	Buy
Strem Chemicals	07-0299	1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride, min. 97%	141556-45-8	1g	$67	2024-03-01	Buy

Product number	Packaging	Price	Buy
574066	1g	$89.4	Buy
574066	5g	$272	Buy
D3446	1g	$68	Buy
D3446	5g	$217	Buy
07-0299	1g	$67	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( 263)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Xilinglab Co., Ltd.	+8618381337976	bd@xilinglab.com	China	86	58
Capot Chemical Co.,Ltd.	+8613336195806	sales@capot.com	China	29731	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21622	55
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	33024	60
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29855	58
Changzhou Ansciep Chemical Co., Ltd.	+86 519 86305871	sales@ansciepchem.com	CHINA	4241	58
Accela ChemBio Inc.	+1-858-6993322	info@accelachem.com	United States	21193	58
Alchem Pharmtech,Inc.	8485655694	sales@alchempharmtech.com	United States	63687	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49733	58
Richest Group Ltd	18017061086	oled@richest-group.com	CHINA	5600	58

Supplier	Advantage
Xilinglab Co., Ltd.	58
Capot Chemical Co.,Ltd.	60
Henan Tianfu Chemical Co.,Ltd.	55
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
Changzhou Ansciep Chemical Co., Ltd.	58
Accela ChemBio Inc.	58
Alchem Pharmtech,Inc.	58
CONIER CHEM AND PHARMA LIMITED	58
Richest Group Ltd	58

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	US $0.00-0.00 / KG	1KG	98%	1Ton	Henan Aochuang Chemical Co.,Ltd.
2022-09-27	1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8	US $0.00 / kg	1kg	99%	1000kg	henan kanbei chemical co.,ltd
2021-07-02	1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE 141556-45-8	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
141556-45-8
US $0.00-0.00 / KG
98%
Henan Aochuang Chemical Co.,Ltd.

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

1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
141556-45-8
US $15.00-10.00 / KG
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-DIMESITYLIMIDAZOLIUM CHLORIDE 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE 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% IMes.HCl 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-DiMesityl-1H-iMidazol-3-iuM chloride 1,3-bis(2,4,6-triMethylphenyl)iMidazol-1-iuM,chloride 1,3-Dimesitylimidazoliumchloride,96% 1,3-Bis(mesityl)imidazolium chloride 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 IMESCL 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-1-ium 1,3-DimesitylimidazoliumChloride> 1H-Imidazolium, 1,3-bis(2,4,6-trimethylphenyl)-, chloride (1:1) 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 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