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1,3-Dimesitylimidazolium chloride_Molecular_structure_CAS_141556-45-8)
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1,3-Dimesitylimidazolium chloride

Catalog No. H27535 Name Alfa Aesar
CAS Number 141556-45-8 Website
M. F. C21H25ClN2 Telephone
M. W. 340.8896 Fax
Purity 96% Email
Storage Chembase ID: 153036

SYNONYMS

Title
1,3-二(2,4,6-三甲基苯基)氯化咪唑
IUPAC name
1,3-bis(2,4,6-trimethylphenyl)-3H-1λ5-imidazol-1-ylium chloride
IUPAC Traditional name
1,3-bis(2,4,6-trimethylphenyl)-1λ5-imidazol-1-ylium chloride
Synonyms
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

DATABASE IDS

MDL Number MFCD02684541
CAS Number 141556-45-8

PROPERTIES

Purity 96%
Melting Point >300°C
GHS Pictograms GHS07
GHS Hazard statements H315-H319-H335
European Hazard Symbols Irritant Irritant (Xi)
GHS Precautionary statements P261-P305+P351+P338-P302+P352-P321-P405-P501A
Risk Statements 36/37/38
Safety Statements 26-37
TSCA Listed

DETAILS

REFERENCES

  • See also 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, H27150.
  • In the presence of a base such as KO-t-Bu, generates the imidazol-2-ylidene, an example of an N-heterocyclic carbene (NHC). NHCs are relatively strong bases, and valuable replacements for phosphine ligands in transition metal chemistry. They are relatively stable to dimerization, but sensitive to air and moisture, so are best generated in situ. Review: Angew. Chem. Int. Ed., 36, 2163 (1997). For a review of stable carbenes, see: Chem. Rev., 100, 39 (2000).
  • Used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction), see: J. Am. Chem. Soc., 121, 9889 (1999). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides, see: J. Org. Chem., 64, 3804 (1999); J. Organomet. Chem., 595, 186 (2000); Tetrahedron Lett., 45, 3511 (2004). Has been found to give superior results to phosphines in the coupling of sulfonyl chlorides with boronic acids: Org. Lett., 6, 95 (2004).
  • The carbene has also been reported to be an excellent nucleophilic catalyst in transesterification reactions, milder, more selective and more active than conventional systems: Org. Lett., 4, 3583, 3587 (2002).