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656631

Sigma-Aldrich

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

95%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C21H27ClN2
Número de CAS:
173035-10-4
Peso molecular:
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

Categorías relacionadas

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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)
S. Roy and H. Plenio,
Advanced Synthesis & Catalysis, 352, 1014-1022 (2010)
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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