ChemicalBook > CAS DataBase List > 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE

Product Name
1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
CAS No.
173035-10-4
Chemical Name
1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
Synonyms
SIMes.HCl;1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride;1,3-diMesityl-4,5-dihydro-1H-iMidazol-3-iuM chloride;1,3-Bis(2;inium ChL;1,3-Bis-(2,4,6-;1,3-Dimesitylimidazolidinium chloride;1,3-DiMesityliMidazolidin-1-iuM chloride;1,3-Bis-(2,4,6-trimethylphenyl)imidazolidinium;4,5-Dihydro-1,3-dimesityl-1H-imidazolium chloride
CBNumber
CB0197636
Molecular Formula
C21H29ClN2
Formula Weight
344.92
MOL File
173035-10-4.mol
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1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Property

Melting point:
280-286 °C
storage temp. 
Inert atmosphere,Room Temperature
form 
Powder
color 
Beige to pink-brown
Sensitive 
air sensitive
InChI
InChI=1S/C21H28N2.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;/h9-12H,7-8,13H2,1-6H3;1H
InChIKey
COGMCBFILULEOS-UHFFFAOYSA-M
SMILES
N1(CCN(C2=C(C)C=C(C)C=C2C)C1)C1C(C)=CC(C)=CC=1C.Cl
CAS DataBase Reference
173035-10-4
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
37/39-26-36
WGK Germany 
3
TSCA 
No
HS Code 
29332990
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
656631
Product name
1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride
Purity
95%
Packaging
1g
Price
$76.11
Updated
2025/07/31
Sigma-Aldrich
Product number
656631
Product name
1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride
Purity
95%
Packaging
5g
Price
$160
Updated
2025/07/31
TCI Chemical
Product number
B3158
Product name
1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$71
Updated
2025/07/31
TCI Chemical
Product number
B3158
Product name
1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$247
Updated
2025/07/31
Strem Chemicals
Product number
07-4011
Product name
1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride, min. 97%
Packaging
500mg
Price
$53
Updated
2024/03/01
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1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Chemical Properties,Usage,Production

Chemical Properties

beige to pink-brown powder

Uses

N-Heterocyclic Carbene Ligands Precursor to an N-heterocyclic carbene catalysts

Uses

N-Heterocyclic Carbene Ligands

Precursor to an N-heterocyclic carbene catalysts used for:

  • A regioselective cycloadditon of terminal acetylenes with azides leading to 1,4-disubstitutedtriazoles. Internal acetylenes can also be used with this catalyst.
  • Markovnikov-type hydration of terminal alkynes
  • Hydrosilylation of ketones and cycloaddition of azides and alkynes
  • Suzuki-Miyaura reactions
  • Luminescence experiments

General Description

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride is an NHC (N-heterocyclic carbene) ligand which can bind with metal pre-catalysts to form complexes that show high catalytic activity.

reaction suitability

reagent type: ligand

Synthesis

122-51-0

258278-23-8

173035-10-4

Sodium borohydride (NaBH4, 4.24 g, 112.1 mmol) was slowly added to a solution of N,N'-bis(2,4,6-trimethylphenyl)ethylenediamine hydrochloride (8.0 g, 27.3 mmol) in tetrahydrofuran (THF, 100 mL) at 0 °C. Subsequently, concentrated hydrochloric acid (HCl, 4.5 mL, 2 eq.) was added dropwise over 30 min. After the dropwise addition, the reaction mixture was continued to be stirred at 0 °C for 20 min. Next, 3M hydrochloric acid (250 mL) was carefully added to the reaction flask at 0°C and the mixture was stirred for 1 hour, during which time the temperature was allowed to naturally rise to room temperature. Upon completion of the reaction, the white precipitate was collected by filtration and washed sequentially with water (200 mL) and 5% acetone-ether mixture (150 mL). The resulting product (9.4 g, 93% yield) was a white solid, which was dried under vacuum and prepared for use. The above obtained hydrochloride (8.5 g, 23 mmol) was suspended in triethyl orthoformate (HC(OEt)3, 35 mL, 162 mmol) and 2 drops of formic acid (HCO2H, ca. 1 mol%) was added as catalyst. The reaction mixture was heated to 120 °C and maintained for 5 hours under argon (Ar) protection. At the end of the reaction, it was cooled to room temperature and hexane (200 mL) was added to precipitate the product. After stirring for 1 hour, the white precipitate was collected by filtration, washed with hexane (200 mL) and dried under vacuum to give the final 1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride (IMesH2-HCl, 7.6 g, 96% yield).

References

[1] Synlett, 2006, # 3, p. 493 - 495
[2] Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2546 - 2558
[3] Patent: US9403854, 2016, B2. Location in patent: Page/Page column 41
[4] Tetrahedron, 1999, vol. 55, # 51, p. 14523 - 14534
[5] Organic Syntheses, 2010, vol. 87, p. 77 - 87

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE Suppliers

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View Lastest Price from 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
1,3-Dimesitylimidazolidin-1-ium chloride 173035-10-4
Price
US $2.00-5.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2025-06-20
XINXIANG RUNYU MATERIAL CO., LTD.
Product
1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE 173035-10-4
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100KG
Release date
2024-06-19
Zhuozhou Wenxi import and Export Co., Ltd
Product
1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride 173035-10-4
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

173035-10-4, 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDERelated Search:

1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE 1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold(I)chloride,95% Ruthenium(III) chloride hydrate (1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE DICHLORO-[1,3-BIS(DIISOPROPYLPHENYL)IMIDAZOLYLIDENE]-(3-CHLOROPYRIDYL)PALLADIUM(II) (1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE)DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)RUTHENIUM GRUBBS CATALYST 2ND GENERATION 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II)dichloride Umicore M42 Tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis(2,4,6-triMethylphenyl)-4,5-dihydroiMidazol-2-ylidene]rutheniuM(II) Umicore M41 (1,3-BIS(2,4,6-TRIMETHYLPHENYL)-2-IMIDA& Isopentenylidene(1,3-dimesitylimidazolidin-2-ylidene) (tricyclohexylphosphine)ruthenium(II) dichloride RUTHENIUM, [1,3-BIS(2,4,6-TRIMETHYLPHENYL)-2-IMIDAZOLIDINYLIDENE]DICHLORO-[[2-ISOPROPOXY-5-(N-RESIN-LINKED AMINOSULFONYL)PHENYL]METHYLENE] TRICYCLOHEXYLPHOSPHINE[1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE][(PHENYLTHIO)METHYLENE]RUTHENIUM (II) DICHLORIDE [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)bis(3-bromopyridine)ruthenium(II)

  • N,Nμ-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride
  • SIMes.HCl
  • 1,3-Bis(2,4,6-trimethylphenyl)-imidazolidinium-chlorid
  • 1,3-Bis(2
  • 1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDRO-1H-IMIDAZOLIUM CHLORIDE
  • 1,3-Bis-(2,4,6-trimethyl-phenyl)-imidazolidin-1-ium chloride
  • 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
  • 1,3-Bis-(2,4,6-trimethylphenyl)imidazolidinium
  • inium ChL
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolidiniumchloride,97%
  • 1,3-Bis-(2,4,6-
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolidinium-chloride,98+%,TLC
  • 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride, min. 97%
  • 1,3-Bis-(2,4,6-triMethylphenyl)-4,5-dihydro-3H-iMidazol-1-iuM chloride
  • 1,3-diMesityl-4,5-dihydro-1H-iMidazol-3-iuM chloride
  • 1,3-Bis(2,4,6-triMethlyphenyl)iMidazoliniuM Chloride
  • 1,3-DiMesityliMidazolidin-1-iuM chloride
  • 1,3-Bis(2,4,6-triMethylphenyl)iMidazoliniuM chloride 95%
  • 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride,97%
  • 1,3-Dimesitylimidazolidinium chloride
  • 4,5-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride
  • 4,5-Dihydro-1,3-dimesityl-1H-imidazolium chloride
  • 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-1-ium chloride
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride, SIMes.HCl
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chloride &gt
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium Chlori
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazole hydrochloride
  • 173035-10-4
  • C21H29ClN2
  • C21H28N
  • C21H27ClN2
  • C23H33N
  • Achiral Nitrogen
  • NHC
  • Ligands
  • N-Heterocyclic Carbene Ligands
  • Synthetic Organic Chemistry