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656631

Sigma-Aldrich

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

95%

Synonym(s):
4,5-Dihydro-1,3-dimesityl-1H-imidazolium chloride, N,N′-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride, 1,3-Dimesitylimidazolidinium chloride, 4,5-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride
Empirical Formula (Hill Notation):
C21H27ClN2
CAS Number:
Molecular Weight:
342.91
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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