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656631 Sigma-Aldrich

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

95%

Synonym: 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

  • CAS Number 173035-10-4

  • Empirical Formula (Hill Notation) C21H27ClN2

  • Molecular Weight 342.91

  •  MDL number MFCD09039279

  •  PubChem Substance ID 24884213

  •  NACRES NA.22

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Properties

Related Categories Carbon-Donor Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, NHC Compounds
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

Description

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

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

N-Heterocyclic Carbene Ligands in Chemical Synthesis

Rapid progress in cross-coupling reactions of unactivated substrates catalyzed by metal complexes has transformed the chemical marketplace through introduction of an extensive library of achiral and ...
Keywords: Aminations, Arylations, Catalysis, Coupling reactions, Cross couplings, Cyclizations, Eliminations, Hydrogenations, Ligands, Metathesis, Oxidative additions, Reductive eliminations

N-Heterocyclic Carbene Ligands

NHC (N-heterocyclic carbenes) have evolved to become powerful, universal ligands for the rapid synthesis of novel organometallic complexes.1 In particular, NHC ligands have found practical use when b...
ChemFiles 2006, 6.8, 14.
Keywords: Catalysis, Electronics, Hydrosilylations, Immobilization, Ligands

NHC Ligands

Rapid progress in cross-coupling reactions of unactivated substrates catalyzed by metal complexes has transformed the chemical market-place through introduction of an extensive library of achiral and...
ChemFiles Volume 5 Article 10
Keywords: Aminations, Arylations, Catalysis, Coupling reactions, Cross couplings, Cyclizations, Eliminations, Hydrogenations, Ligands, Metathesis, Oxidative additions, Reductive eliminations

Related Content

N-Heterocyclic Carbene Ligands - Chemical Synthesis

Rapid progress in cross-coupling reactions of unactivated substrates catalyzed by metal complexes has transformed the chemical marketplace through introduction of an extensive library of achiral and ...
Keywords: Aminations, Arylations, Catalysis, Coupling reactions, Cross couplings, Cyclizations, Eliminations, Hydrogenations, Ligands, Metathesis, Oxidative additions, Reductive eliminations

Peer-Reviewed Papers
15

References

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