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

• ChemBase编号: 153036
• 分子式: C21H25ClN2
• 平均质量: 340.8896
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: 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
• 别名: 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; 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

登记号

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

理论计算性质

• Acid pKa: 19.539106
• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 4.308309
• LogD (pH = 7.4): 4.308309
• Log P: 4.308309
• 摩尔折射率: 119.2937 cm^3
• 极化性: 38.612583 Å^3
• 极化表面积: 8.81 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: >300 °C(lit.); >300°C

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

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

详细说明

Sigma Aldrich - 574066

包装
1, 5 g in glass bottle

参考文献

• 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).