1,3-bis(2,4,6-trimethylphenyl)-3H-1λ5-imidazol-1-ylium chloride

• ChemBase ID: 153036
• Molecular Formular: C21H25ClN2
• Molecular Mass: 340.8896
• Monoisotopic Mass: 340.17062649
• SMILES: Cc1cc(c(c(c1)C)n1cc[n+](c1)c1c(cc(cc1C)C)C)C.[Cl-]
• Canonical SMILES: Cc1cc(C)c(c(c1)C)n1cc[n+](c1)c1c(C)cc(cc1C)C.[Cl-]
• InChI: InChI=1S/C21H25N2.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;/h7-13H,1-6H3;1H/q+1;/p-1
• InChIKey: OTOSIXGMLYKKOW-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis(2,4,6-trimethylphenyl)-3H-1λ^5-imidazol-1-ylium chloride; 1,3-bis(2,4,6-trimethylphenyl)-3H-1λ^5,3-imidazol-1-ylium chloride
• IUPAC Traditional name: 1,3-bis(2,4,6-trimethylphenyl)-1λ^5-imidazol-1-ylium chloride; 1,3-bis(2,4,6-trimethylphenyl)-1λ^5,3-imidazol-1-ylium chloride
• Synonyms: 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride; 1,3-Dimesitylimidazolium chloride; 1,3-Bis(mesityl)imidazolium chloride; 1,3-Dihydro-1,3-dimesityl-2H-imidazol-2-ylidene monohydrochloride; 1,3-Dimesitylimidazolium chloride; 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride; 1,3-二(2,4,6-三甲基苯基)氯化咪唑; 1,3-双(2,4,6-三甲基苯基)氯化咪唑

Database IDs

• CAS Number: 141556-45-8
• MDL Number: MFCD02684541
• PubChem SID: 162247176; 24880704
• PubChem CID: 2734211

CALCULATED PROPERTIES

• Acid pKa: 19.539106
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.308309
• LogD (pH = 7.4): 4.308309
• Log P: 4.308309
• Molar Refractivity: 119.2937 cm^3
• Polarizability: 38.612583 Å^3
• Polar Surface Area: 8.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C21H25ClN2

DETAILS

Sigma Aldrich - 574066

Packaging
1, 5 g in glass bottle

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).