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656631

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

Name: 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride
Brand: ALDRICH

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

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₇ClN₂

CAS Number:

173035-10-4

Molecular Weight:

342.91

NACRES:

NA.22

PubChem Substance ID:

24884213

UNSPSC Code:

12352005

MDL number:

MFCD09039279

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Properties

Quality Level

100

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

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

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Articles

N-Heterocyclic Carbene Ligands

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

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

N-Heterocyclic Carbene (NHC) Ligands

Emerging class of privileged ligands

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C. E. Czegeni, et al.,

J. Mol. Catal. A: Chem., 340, 1-8 (2011)

(NHC)Copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes.

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

S. Roy and H. Plenio,

Advanced Synthesis & Catalysis, 352, 1014-1022 (2010)

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Global Trade Item Number

SKU	GTIN
656631-5G	04061832733326
656631-1G	04061832733319