chlorodimethylphenylsilane

• ChemBase ID: 80162
• Molecular Formular: C8H11ClSi
• Molecular Mass: 170.71144
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: chlorodimethylphenylsilane
• IUPAC Traditional name: chlorodimethylphenylsilane
• Synonyms: chloro(dimethyl)phenylsilane; DMPSCl; Dimethylphenylchlorosilane; Dimethylphenylsilylchloride; Phenyldimethylchlorosilane; Chloro(dimethyl)phenylsilane; Dimethylphenylsilyl chloride; Chlorodimethylphenylsilane; Chlorodimethyl(phenyl)silane; 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

Database IDs

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

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3339
• LogD (pH = 7.4): 2.3339
• Log P: 2.3339
• Molar Refractivity: 43.1708 cm^3
• Polarizability: 18.747343 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 192-193°C; 194-198 °C
• Flash Point: 143.6 °F; 62 °C; 72°C(161°F)
• Density: 1.017 g/mL at 25 °C(lit.); 1.032
• Refractive Index: 1.5090; n20/D 1.508; n20/D 1.509(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2987; UN2987
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34; 34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H227
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: 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

Product Information

• Purity: ≥96.0% (AT); 97%; 97+%; 98%
• Grade: purum
• Linear Formula: C6H5Si(CH3)2Cl

DETAILS

Sigma Aldrich - 113379

Application
Used in a synthesis of enantioenriched allenylsilanes via an ortho-ester Claisen rearrangement of chiral, silylpropargylic alcohols.1
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 78390

Other Notes
Silylating agent1,2; The lithium derivative is formed smoothly with lithium, used for addition reactions3,4

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).