chlorodimethylphenylsilane

• ChemBase编号: 80162
• 分子式: C8H11ClSi
• 平均质量: 170.71144
• 单一同位素质量: 170.03185456
• SMILES: [Si](c1ccccc1)(Cl)(C)C
• Canonical SMILES: C[Si](c1ccccc1)(Cl)C
• InChI: InChI=1S/C8H11ClSi/c1-10(2,9)8-6-4-3-5-7-8/h3-7H,1-2H3
• InChIKey: KWYZNESIGBQHJK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: chlorodimethylphenylsilane
• IUPAC传统名: chlorodimethylphenylsilane
• 别名: 二甲基苯基氯硅烷; 二甲基苯基硅基氯; 苯基二甲基氯硅烷; 氯(二甲基)苯基硅烷; 二甲基苯基氯硅烷; chloro(dimethyl)phenylsilane; DMPSCl; Dimethylphenylchlorosilane; Dimethylphenylsilylchloride; Phenyldimethylchlorosilane; Chloro(dimethyl)phenylsilane; Dimethylphenylsilyl chloride; Chlorodimethylphenylsilane; Chlorodimethyl(phenyl)silane

登记号

• CAS号: 768-33-2
• EC号: 212-193-0
• MDL号: MFCD00000499
• Beilstein号: 606292
• PubChem SID: 24846878; 162067282; 24887297
• PubChem CID: 13029

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.3339
• LogD (pH = 7.4): 2.3339
• Log P: 2.3339
• 摩尔折射率: 43.1708 cm^3
• 极化性: 18.747343 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 192-193°C; 194-198 °C
• 闪点: 143.6 °F; 62 °C; 72°C(161°F)
• 密度: 1.017 g/mL at 25 °C(lit.); 1.032
• 折射率: 1.5090; n20/D 1.508; n20/D 1.509(lit.)

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 2987; UN2987
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 34; 34-37
• 安全公开号: 26-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318-H227
• GHS警示性声明: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2987 8/PG 2

产品相关信息

• 纯度: ≥96.0% (AT); 97%; 97+%; 98%
• 级别: purum
• 线性分子式: C6H5Si(CH3)2Cl

详细说明

Sigma Aldrich - 113379

Application
用于通过手性硅基炔丙醇的原酸酯 Claisen 重排反应合成对映体富集的联烯硅烷。1
包装
5, 25 g in glass bottle

Sigma Aldrich - 78390

Other Notes
硅烷化试剂1,2；可与锂发生平稳反应形成锂衍生物，该锂衍生物可用于加成反应3,4

参考文献

• See also: J. Chem. Soc., Perkin 1, 1209 (1998).
• Silylating agent (see Appendix 4): J. Chromat., 147, 291 (1978). Dimethylphenylsilyl (DMPS) ethers are somewhat more resistant to hydrolysis than TMS and are useful in the chromatographic analysis of monosaccharides with UV detection: J. Chromat., 264, 99 (1983); Carbohydr. Res., 119, 241 (1983). See also Dimethylphenylsilane, L04558. The lithio-derivatives of esters and lactones are silylated by DMPSCl on carbon (TMSCl gives O-silylation): J. Am. Chem. Soc., 103, 2418 (1981).
• The reactions of various metallated DMPS derivatives have been extensively studied by Fleming's group and others. DMPSLi gives an organocopper species with CuI which undergoes conjugate addition to enones, to give ?-silyl ketones: J. Chem. Soc., Perkin 1., 2520 (1981):
  
• For a study of diastereoselectivity in the preparation of ?-silyl esters from ɑ?-unsaturated esters and amides attached to chiral auxiliaries, see: J. Chem. Soc., Perkin 1, 303 (1995). For a brief feature on Phenyldimethylsilyllithium, see: Synlett, 1522 (2000).
• The DMPS group attached to carbon may function as a masked OH group. Protodesilylation gives the silyl fluoride, which can be converted to the alcohol with overall retention of configuration by reaction with m-CPBA, peracetic acid/Br₂, or peracetic acid/Mg(OAc)₂ with or without Pd(II) catalysis. For a detailed study, see: J. Chem. Soc., Perkin 1, 317 (1995):
  
• Aryl-, alkenyl- and alkynyldimethylchlorosilanes undergo homo-coupling in the presence of TBAF and a catalytic amount of CuI to give biaryls or the corresponding symmetrical dienes or diynes in high yield: J. Chem. Soc., Perkin 1, 797 (1997).