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775-12-2 - Diphenylsilane, 97% - A10884 - Alfa Aesar

A10884 Diphenylsilane, 97%

CAS Number
775-12-2
Synonyms

Size Price ($) Quantity Availability
5g 26.01
25g 86.31
100g 271.20
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Diphenylsilane, 97%

MDL
MFCD00003002
EINECS
212-271-4

Chemical Properties

Formula
C12H12Si
Formula Weight
184.32
Boiling Point
95-97°/13mm
Flash Point
98°(208°F)
Density
0.996
Refractive Index
1.5790
Solubility
Decomposes in water.

Applications

Thiocarbonyl derivatives of secondary alcohols are readily reduced by diphenylsilane in a radical chain process at room temperature using triethylborane-air as an initiator. An improved radical chain procedure for the deoxygenation of secondary and primary alcohols using diphenylsilane as hydrogen atom donor and triethylborane-air as initiator. Diphenylsilane is a reagent in the invention of radical reactions for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry. Fluorescent film sensor for vapor-phase nitroaromatic explosives via monolayer assembly of oligo(diphenylsilane) on glass plate surfaces. Reductions of carboxylic acid derivatives by silanes in the presence of rhodium complexes were studied. Carboxylic esters were reduced to alcohols by diphenylsilane catalyzed by [RhCl (cod)] 2/4PPh 3 or [RhCl (PPh 3) 3] at room temperature in up to 99% yields. Sequential C- Si bond formations from diphenylsilane and its application to silanediol peptide isostere precursors.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents, bases, haevy metal powders.

Literature References

John L. Speier,; Ruth Zimmerman,; James Webster. The Addition of Silicon Hydrides to Olefinic Double Bonds. Part I. The Use of Phenylsilane, Diphenylsilane, Phenylmethylsilane, Amylsilane and Tribromosilane. J. Am. Chem. Soc., 1956, 78 (10), 2278-2281.

Lone Nielsen and Troels Skrydstrup. Lone Nielsen and Troels Skrydstrup. J. Am. Chem. Soc., 2008, 130 (39), 13145-13151.

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, ɑß-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):

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280g-P305+P351+P338

Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Other References

Beilstein
2935887
Harmonized Tariff Code
2931.90
TSCA
Yes

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