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

• ChemBase编号: 139557
• 分子式: C27H37ClN2
• 平均质量: 425.04908
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: 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
• 别名: 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; 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

登记号

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

理论计算性质

• Acid pKa: 19.50345
• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 6.207817
• LogD (pH = 7.4): 6.207817
• Log P: 6.207817
• 摩尔折射率: 145.8097 cm^3
• 极化性: 49.856335 Å^3
• 极化表面积: 8.81 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

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

安全信息

• 保存注意事项: Hygroscopic
• 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: 97%; 98%
• Empirical Formula (Hill Notation): C27H37ClN2

详细说明

Sigma Aldrich - 574074

Application
与乙酸钯共同用于生成 N-杂环卡宾催化剂，该催化剂用于吡啶卤化物与芳基硼酸的羰基化交叉偶联反应。1
包装
2 g in glass bottle
500 mg in glass bottle

参考文献

• 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.