diphenylsilane

• ChemBase ID: 107424
• Molecular Formular: C12H12Si
• Molecular Mass: 184.30918
• Monoisotopic Mass: 184.07082692
• SMILES: [SiH2](c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)[SiH2]c1ccccc1
• InChI: InChI=1S/C12H12Si/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H,13H2
• InChIKey: VDCSGNNYCFPWFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenylsilane
• IUPAC Traditional name: diphenylsilane
• Synonyms: DIPHENYLSILANE; Diphenylsilane; 二苯基硅烷

Database IDs

• CAS Number: 775-12-2
• EC Number: 212-271-4
• MDL Number: MFCD00003002
• Beilstein Number: 2935887
• PubChem SID: 24848906; 24867106; 162093988
• PubChem CID: 6327659

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.5974
• LogD (pH = 7.4): 2.5974
• Log P: 2.5974
• Molar Refractivity: 52.5486 cm^3
• Polarizability: 22.940939 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 95-97 °C/13 mmHg(lit.); 95-97°C/13mm
• Flash Point: 208.4 °F; 98 °C; 98°C(208°F)
• Density: 0.993 g/mL at 25 °C(lit.); 0.996
• Refractive Index: 1.5790; n20/D 1.579; n20/D 1.579(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38; 38; R:36/37/38
• Safety Statements: 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315; H315-H319
• GHS Precautionary statements: P280G-P305+P351+P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (GC); 95+%; 97%
• Grade: purum
• Linear Formula: (C6H5)2SiH2

DETAILS

MP Biomedicals - 05203681

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 148482

Packaging
5, 25 g in ampule

Sigma Aldrich - 43290

Other Notes
Reagent used in the highly selective hydrosilylation of carbonyl compounds1,2,3; Radical-induced deoxigenations4

REFERENCES

• Protection of diols as diphenylsilylenes can be effected in the presence of CsF: J. Organomet. Chem., 282, 155 (1985). See Diphenyldichlorosilane, A12051, and Appendix 4.
• Reducing agent used in combination with F^- or other catalyst.
• CsF promotes the reduction of aldehydes and ketones to alcohols: J. Organomet. Chem., 148, C1 (1978); 172, 143 (1979). Esters can be reduced at elevated temperatures: Synthesis, 558 (1981). Aldehydes and ketones are also reduced in the presence of TBAF: J. Org. Chem., 53, 5415 (1988).
• In the presence of Tetrakis(triphenylphosphine)palladium(0), 10548, effects the reductive cleavage of allylic acetates: J. Org. Chem., 48, 3545 (1983). With the same catalyst and a Lewis acid such as zinc chloride, ɑ?-unsaturated aldehydes, ketones and esters are reduced to their saturated counterparts: J. Am. Chem. Soc., 108, 7314 (1986).
• In combination with an equivalent of Titanium(IV) isopropoxide, A13703, a mild, one-pot reduction of tertiary amides to aldehydes can be accomplished in high yield. The initial product is the enamine which can be readily hydrolyzed in situ to the aldehyde: Angew. Chem. Int. Ed., 35, 1515 (1996):