1,3-bis[2,6-bis(propan-2-yl)phenyl]-3H-1λ5-imidazol-1-ylium chloride

• ChemBase ID: 139557
• Molecular Formular: C27H37ClN2
• Molecular Mass: 425.04908
• Monoisotopic Mass: 424.26452687
• SMILES: CC(C)c1cccc(c1n1cc[n+](c1)c1c(cccc1C(C)C)C(C)C)C(C)C.[Cl-]
• Canonical SMILES: CC(c1cccc(c1n1cc[n+](c1)c1c(cccc1C(C)C)C(C)C)C(C)C)C.[Cl-]
• InChI: InChI=1S/C27H37N2.ClH/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;/h9-21H,1-8H3;1H/q+1;/p-1
• InChIKey: AVJBQMXODCVJCJ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis[2,6-bis(propan-2-yl)phenyl]-3H-1λ^5-imidazol-1-ylium chloride; 1,3-bis[2,6-bis(propan-2-yl)phenyl]-3H-1λ^5,3-imidazol-1-ylium chloride
• IUPAC Traditional name: 1,3-bis(2,6-diisopropylphenyl)-1λ^5-imidazol-1-ylium chloride; 1,3-bis(2,6-diisopropylphenyl)-1λ^5,3-imidazol-1-ylium chloride
• Synonyms: 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride; 1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene; 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1H-imidazolium chloride; 2,5-Bis(2,6-diisopropylphenyl)imidazolium chloride; 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride; 1,3-二(2,6-二异丙基苯基)氯化咪唑; 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓

Database IDs

• CAS Number: 250285-32-6
• MDL Number: MFCD02684545
• PubChem SID: 24880705; 162233805
• PubChem CID: 2734913

CALCULATED PROPERTIES

• Acid pKa: 19.50345
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.207817
• LogD (pH = 7.4): 6.207817
• Log P: 6.207817
• Molar Refractivity: 145.8097 cm^3
• Polarizability: 49.856335 Å^3
• Polar Surface Area: 8.81 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 278 °C (dec.)(lit.); ca 280°C dec.

Safety Information

• Storage Warning: Hygroscopic
• 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: 97%; 98%
• Empirical Formula (Hill Notation): C27H37ClN2

DETAILS

Sigma Aldrich - 574074

Application
Used with palladium acetate to generate an N-heterocyclic carbene catalyst for carbonylative cross-coupling of pyridyl halides with aryl boronic acids.1
Packaging
2 g in glass bottle
500 mg in glass bottle

REFERENCES

• 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). For Pd-catalyzed coupling of trimethoxysilanes with electron-deficient aryl chlorides, see: Org. Lett., 2, 2053 (2000). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-bis(2,6-diisopropylphenyl)imiazol-2-ylidene, enabling otherwise difficult coupling reactions of aryl chlorides with aryl and alkyl boronic acids, see: Synlett, 292 (2001) (includes alkylboronic acids: better yields than 1,3-dimesitylimidazol-2-ylidene); Org. Lett., 6, 4435 (2004); Tetrahedron Lett., 45, 3511 (2004).
• See also 1,3-Dimesitylimidazolium chloride, H27535.