trimethyl(phenylsulfanyl)silane

• ChemBase ID: 150134
• Molecular Formular: C9H14SSi
• Molecular Mass: 182.35796
• Monoisotopic Mass: 182.05854798
• SMILES: C[Si](C)(C)Sc1ccccc1
• Canonical SMILES: C[Si](Sc1ccccc1)(C)C
• InChI: InChI=1S/C9H14SSi/c1-11(2,3)10-9-7-5-4-6-8-9/h4-8H,1-3H3
• InChIKey: VJMQFIRIMMSSRW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethyl(phenylsulfanyl)silane
• IUPAC Traditional name: trimethyl(phenylsulfanyl)silane
• Synonyms: S-Trimethylsilylthiophenol; (Phenylthio)trimethylsilane; Phenyl trimethylsilyl sulfide; S-(Trimethylsilyl)thiophenol; (Phenylthio)trimethylsilane; Trimethyl(phenylthio)silane; (苯硫基)三甲基硅烷; (苯硫基)三甲基硅烷; 苯基硫三甲基硅烷

Database IDs

• CAS Number: 4551-15-9
• EC Number: 224-916-7
• MDL Number: MFCD00008272
• Beilstein Number: 1905944
• PubChem SID: 24887420; 24853570; 162244296
• PubChem CID: 78312

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.8372
• LogD (pH = 7.4): 3.8372
• Log P: 3.8372
• Molar Refractivity: 48.5704 cm^3
• Polarizability: 21.85331 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 72 °C/8 mmHg(lit.); 73-75°C/10mm
• Flash Point: 30°C(86°F); 33 °C; 91.4 °F
• Density: 0.963 g/mL at 25 °C(lit.); 0.965
• Refractive Index: 1.5320; n20/D 1.53; n20/D 1.532(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-20-38; 10-36/37/38
• Safety Statements: 23-26-37; 23-28
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335; H226-H315-H332
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥98.0% (GC); 97%
• Grade: purum
• Linear Formula: C6H5SSi(CH3)3

DETAILS

Sigma Aldrich - 226467

Packaging
5 g in ampule

Sigma Aldrich - 79222

Other Notes
Reagent for protecting carbonyls to S-Phe monothio-acetals; the phenylthio group can be stereoselectively reduced to an alkyllithium1; for the cleavage of methyl and benzyl ethers2

REFERENCES

• Thioacetalization reagent. In the presence of CN^-, aldehydes and ketones are converted to O-TMS hemithioacetals J. Am. Chem. Soc., 99, 5009 (1977). With Lewis acids, e.g. TiCl₄, the diphenyl dithioacetals can be obtained in good yield J. Org. Chem., 55, 5966 (1990). Aldehydes and ketones can be converted to the otherwise difficultly accessible mixed O-alkyl, S-phenyl acetals by the reagent in the presence of the alkyl TMS ether and TMS triflate: Tetrahedron Lett., 32, 467 (1991).
• In the presence of TMS-OTf, converts methyl glycosides to phenylthio glycosides. These undergo methanolysis, after activation by reaction with NBS: J. Am. Chem. Soc., 105, 2430 (1983); 107, 1691 (1985).
• In the presence of ZnI₂ and tetrabutylammonium iodide, cleaves methyl and benzyl ethers in high yield: Tetrahedron Lett., 2305 (1980).