Diphenylsilane, 97%, Thermo Scientific Chemicals
Diphenylsilane, 97%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

Diphenylsilane, 97%, Thermo Scientific Chemicals

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25 g
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100 g
Catalog number A10884.14
also known as A10884-14
Price (USD)/ Each
105.65
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117.00 
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Quantity:
25 g
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Price (USD)/ Each
105.65
Online exclusive
117.00 
Save 11.35 (10%)
Add to cart
Diphenylsilane, 97%, Thermo Scientific Chemicals
Catalog numberA10884.14
Price (USD)/ Each
105.65
Online exclusive
117.00 
Save 11.35 (10%)
-
Add to cart
Chemical Identifiers
CAS775-12-2
IUPAC Namediphenylsilane
Molecular FormulaC12H12Si
InChI KeyVDCSGNNYCFPWFK-UHFFFAOYSA-N
SMILES[SiH2](C1=CC=CC=C1)C1=CC=CC=C1
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)Clear colorless
FormLiquid
Assay (GC)≥96.0%
Identification (FTIR)Conforms
Refractive Index1.5765-1.5815 @ 20?C

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.
RUO – Research Use Only

General References:

  1. 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.
  2. Lone Nielsen and Troels Skrydstrup. Lone Nielsen and Troels Skrydstrup. J. Am. Chem. Soc., 2008, 130 (39), 13145-13151.
  3. Protection of diols as diphenylsilylenes can be effected in the presence of CsF: J. Organomet. Chem., 282, 155 (1985). See Diphenyl dichlorosilane, A12051, and Appendix 4.
  4. Reducing agent used in combination with F- or other catalyst.
  5. 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).
  6. In the presence of Tetrakis(triphenyl phosphine) 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).
  7. 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):