Skip to Content
MilliporeSigma
All Photos(1)

Documents

656631

Sigma-Aldrich

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

95%

Synonym(s):

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, N,N′-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C21H27ClN2
CAS Number:
173035-10-4
Molecular Weight:
342.91
MDL number:
MFCD09039279
UNSPSC Code:
12352005
PubChem Substance ID:
24884213
NACRES:
NA.22

assay

95%

reaction suitability

reagent type: ligand

mp

280-286 °C

SMILES string

[Cl-].Cc1cc(C)c(N2CC[N+](=C2)c3c(C)cc(C)cc3C)c(C)c1

InChI

1S/C21H27N2.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;/h9-13H,7-8H2,1-6H3;1H/q+1;/p-1

InChI key

COGMCBFILULEOS-UHFFFAOYSA-M

Related Categories

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.

Application

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Silvia Díez-González et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(29), 7558-7564 (2006-09-14)
A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high
C. E. Czegeni, et al.,
J. Mol. Catal. A: Chem., 340, 1-8 (2011)
Vonika Ka-Man Au et al.
Journal of the American Chemical Society, 131(25), 9076-9085 (2009-06-03)
A new class of luminescent mononuclear and dinuclear N-heterocyclic carbene-containing gold(III) complexes has been synthesized and characterized. The X-ray crystal structures of most of the complexes have also been determined. Electrochemical studies reveal a ligand-centered reduction originated from the RC--N--CR
S. Roy and H. Plenio,
Advanced Synthesis & Catalysis, 352, 1014-1022 (2010)
V Poza-Nogueiras et al.
Chemosphere, 199, 68-75 (2018-02-13)
Conventional water treatments are generally inadequate for degradation of emerging pollutants such as ionic liquids (ILs). The use of heterogeneous electro-Fenton (HEF) has attracted great interest, due to its ability to efficiently oxidize a wide range of organic pollutants operating
View All Related Papers

Articles

N-Heterocyclic Carbene (NHC) Ligands

Metal complex-catalyzed cross-coupling reactions of unactivated substrates introduce diverse phosphine ligands in chemical marketplace.

N-Heterocyclic Carbene Ligands

A wide range of NHC ligands are commonly available which exhibit high activities.

N-Heterocyclic Carbene (NHC) Ligands

Emerging class of privileged ligands

1-tBu-Indenyl Supported Palladium Precatalysts for Cross-Coupling

The Hazari group has developed an improved palladium precatalyst scaffold for a wide range of cross-coupling reactions

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service