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656631

Sigma-Aldrich

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

95%

Synonyme(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

Formule empirique (notation de Hill):
C21H27ClN2
Numéro CAS:
173035-10-4
Poids moléculaire :
342.91
Numéro MDL:
MFCD09039279
Code UNSPSC :
12352005
ID de substance PubChem :
24884213
Nomenclature NACRES :
NA.22

Pureté

95%

Pertinence de la réaction

reagent type: ligand

Pf

280-286 °C

Chaîne SMILES 

[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

Clé InChI

COGMCBFILULEOS-UHFFFAOYSA-M

Catégories apparentées

Description générale

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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