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

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

95%

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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

Empirical Formula (Hill Notation):

C₂₁H₂₇ClN₂

CAS Number:

173035-10-4

Molecular Weight:

342.91

MDL number:

MFCD09039279

PubChem Substance ID:

24884213

NACRES:

NA.22

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

Related Categories

NHC Ligands & Complexes

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

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Precautionary Statements

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Luminescent cyclometalated N-heterocyclic carbene-containing organogold(III) complexes: synthesis, characterization, electrochemistry, and photophysical studies.

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

[(NHC)CuX] complexes: synthesis, characterization and catalytic activities in reduction reactions and Click chemistry. On the advantage of using well-defined catalytic systems.

Silvia Díez-González et al.

Dalton transactions (Cambridge, England : 2003), 39(32), 7595-7606 (2010-07-14)

The preparation of three series of [(NHC)CuX] complexes (NHC = N-heterocyclic carbene, X = Cl, Br, or I) is reported. These syntheses are high yielding and only use readily available starting materials. The prepared complexes were spectroscopically and structurally characterized.

Heterogeneous electro-Fenton as plausible technology for the degradation of imidazolinium-based ionic liquids.

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

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

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