A15638

Chlorodimethylphenylsilane, 97+%

CAS Number 768-33-2 Synonyms
  • Dimethylphenylchlorosilane
  • Dimethylphenylsilyl chloride

 
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Chlorodimethylphenylsilane, 97+%

MDL: MFCD00000499
EINECS: 212-193-0

Chemical Properties

Formula: C8H11ClSi  Density: 1.032
Formula weight: 170.72  Refractive Index: 1.5090
Boiling point: 192-193° Sensitivity: Moisture Sensitive
Flash point: 72°(161°F) 

Literature References

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 ß-silyl ketones: J. Chem. Soc., Perkin 1., 2520 (1981):

See also: J. Chem. Soc., Perkin 1, 1209 (1998).

For a study of diastereoselectivity in the preparation of ß-silyl esters from ɑß-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).

GHS Hazard and Precautionary Statements

Hazard Statements : H314-H318-H227

Causes severe skin burns and eye damage. Causes serious eye damage. Combustible liquid.

Precautionary Statements : P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Corrosive

Other References

Beilstein: 606292
UN#: UN2987
Hazard Class: 8
Packing Group: II
Harmonized Tariff Code: 2931.90
TSCA: Yes
Chlorodimethylphenylsilane, 97+% - CAS 768-33-2 - Formula C8H11ClSi

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