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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%

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

MDL number:

MFCD09039279

UNSPSC Code:

12352005

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

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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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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(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

C. E. Czegeni, et al.,

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

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

S. Roy and H. Plenio,

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

[(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.

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