Chlorodimethylphenylsilane

• Catalog No.: A15638
• CAS Number: 768-33-2
• M. F.: C8H11ClSi
• M. W.: 170.71144
• Purity: 97+%

SYNONYMS

• Title: 二甲基苯基氯硅烷
• IUPAC name: chlorodimethylphenylsilane
• IUPAC Traditional name: chlorodimethylphenylsilane
• Synonyms: Dimethylphenylsilyl chloride; Dimethylphenylchlorosilane

DATABASE IDS

• EC Number: 212-193-0
• MDL Number: MFCD00000499
• Beilstein Number: 606292
• CAS Number: 768-33-2

PROPERTIES

• Purity: 97+%
• Boiling Point: 192-193°C
• Density: 1.032
• Flash Point: 72°C(161°F)
• Refractive Index: 1.5090
• GHS Hazard statements: H314-H318-H227
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2987
• Packing Group: II

REFERENCES

• 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).