775-12-2

Basic information

• Product Name: Diphenylsilane
• Synonyms: diphenyl-silan;Silane,diphenyl-;TSL8224;DIPHENYLSILANE;Diphenylsilane,min.97%;Diphenylsilane, min. 97%;Diphenylsilane,97%;Diphenylsilane,99%
• CAS NO: 775-12-2
• Molecular Formula: C₁₂H₁₂Si
• Molecular Weight: 184.31
• EINECS: 212-271-4
• Product Categories: Reduction;Si (Classes of Silicon Compounds);Si-H Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Organometallic Reagents;Organosilicon;Others;organosilicon compounds
• Mol File: 775-12-2.mol
• Article Data: 69

Chemical Properties

• Melting Point: 157-161℃
• Boiling Point: 95-97 °C13 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: colorless/liquid
• Density: 0.993 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.184mmHg at 25°C
• Refractive Index: n20/D 1.579(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Decomposes in water.
• Sensitive: Air & Moisture Sensitive
• BRN: 2935887
• CAS DataBase Reference: Diphenylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenylsilane(775-12-2)
• EPA Substance Registry System: Diphenylsilane(775-12-2)

Safety Data

• Hazard Codes: Xi
• Statements: 38-36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 1
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 775-12-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

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.

Application

Used in the preparation of silyl-substituted alkylidene complexes of tantalum. Used in the ionic reduction of enones to saturated ketones. Used in the reductive cyclization of unsaturated ketones. Reduces esters in the presence of zinc hydride catalyst. Reduces α-halo ketones in presence of Mo(0). Reduces thio esters to ethers. Reduces esters to alcohols with Rh catalysis. Employed in the asymmetric reduction of methyl ketones and other ketones. Reductively cleaves allyl acetates.

Purification Methods

Dissolve it in Et2O, mix slowly with ice-cold 10% AcOH. The Et2O layer is then shaken with H2O until the washings are neutral to litmus. Dry over Na2SO4, evaporate the Et2O and distil the residual oil under reduced pressure using a Claisen flask with the take-off head modified into a short column. Ph2SiH2 boils at 257o/760mm, but it cannot be distilled at this temperature because exposure to air leads to flashing, decomposition and formation of silica. It is a colourless, odourless oil, miscible with organic solvents but not H2O. A possible impurity is Ph3SiH which has m 43-45o and would be found in the residue. [West & Rochow J Org Chem 18 303 1953, Benkhesser et al. J Am Chem Soc 74 648 1952, Gilman & Zuech J Am Chem Soc 81 5925 1959, Beilstein 16 IV 1366.]

InChI:InChI=1/C12H12Si/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H,13H2

Upstream product

• 1631-83-0 diphenylsilyl chloride 
• 40869-79-2 [(PPh₃)₂PtH(SiHPh₂)] 
• 694-53-1 phenylsilane 
• 1631-90-9 bromo-phenyl-silane 
• 1111-74-6 dimethylsilane 
• 80-10-4 diphenylsilyl dichloride 
• 3724-36-5 (4-chlorophenyl)silane 
• 13272-84-9 (4-fluorophenyl)silane 
• 126971-98-0 diphenyl(silane-d₁) 
• 17950-94-6 dideuteriodiphenylsilane 
• 944714-00-5 C₃₄H₂₈Si₂ 
• 126990-35-0 dicyclopentyl dimethoxy silane 
• 6843-66-9 dimethoxy(diphenyl)silane 
• 108-86-1 bromobenzene 

Downstream Products

• 17964-31-7 butyldiphenylsilane 
• 1829-58-9 (prop-2-enyl)diphenylsilane 
• 10519-88-7 diallyldiphenylsilane 
• 18754-81-9 decyl-diphenyl-silane 
• 789-25-3 HSiPh₃ 
• 17995-01-6 bromo-diphenyl-silane 
• 4072-00-8 Diphenyldibromsilan 
• 694-53-1 phenylsilane 
• 4206-75-1 phenylchlorosilane 
• 21654-89-7 Bis-<3-chlor-propyl>-diphenyl-silan 
• 2632-94-2 chloro-(3-chloro-propyl)-diphenyl-silane 
• 294-62-2 cyclododecane 
• 834-14-0 p-benzylanizole 
• 73818-10-7 C₁₂H₁₁Si⁽¹⁺⁾ 

Relevant articles and documents

Interconversion of silylphenyl and phenylsilyl cations in the reaction with benzene

The possibility for positive charge migration in SiC6H 7 + cation from carbon to silicon (or vice versa) was studied by the radiochemical method. Silylphenyl cation with initial charge localization on the carbon atom is transformed into phenylsilylium ion where the positive charge is localized on the silicon atom. No migration of positive charge from the silicon atom to carbon occurs. 2005 Pleiades Publishing, Inc.

Palladium(II) catalysed silicon-oxygen bond formation versus rearrangement reactions

Phenylsilane and diphenylsilane undergoes rearrangement reactions by palladium catalysts such as Pd(TMEDA)Cl2, Pd(TEEDA)Cl2, [Pd(PPh3)]2Cl2 (where TMEDA = tetramethylethylenediamine, TEEDA = tetraethylethylenediamine) at room temperature. However, the reductive Si-O bond forming reaction can be performed on hydrosilanes through competitive paths. The reactions of phenylsilane and quinonic compounds are catlaysed by Pd(TMEDA)Cl2 (such as 1,4-benzoquinone, 1,4-napthoquinone) to give siloxanes, backbone of these siloxanes which contains rearranged phenylsilane units. The thin films of such oligomers has plot of resistance vs temperature profile resembling semiconductor.

PROCESS FOR THE STEPWISE SYNTHESIS OF SILAHYDROCARBONS

The invention relates to a process for the stepwise synthesis of silahydrocarbons bearing up to four different organyl substituents at the silicon atom, wherein the process includes at least one step a) of producing a bifunctional hydridochlorosilane by a redistribution reaction, selective chlorination of hydridosilanes with an ether/HCI reagent, or by selective chlorination of hydridosilanes with SiCI4, at least one step b) of submitting a bifunctional hydridochloromonosilane to a hydrosilylation reaction, at least one step c) of hydrogenation of a chloromonosilane, and a step d) in which a silahydrocarbon compound is obtained in a hydrosilylation reaction.

CATALYTIC REDUCTION OF HALOGENATED CARBOSILANES AND HALOGENATED CARBODISILANES

Selective reduction methods for halogenated carbosilanes and carbodisilanes are disclosed. More particularly, high yields of the desired carbosilanes and carbodisilanes are obtained by reduction of their halogenated counterparts using a reducing agent and tetrabutylphosphonium chloride (TBPC) as a catalyst.

An effective total synthesis of four angiotensin-converting enzymes containing silanediols

Four angiotensin-converting enzymes (ACE) containing silanediols 1 have been synthesized successfully in 8% overall yield in 8 steps from inexpensive starting materials such as diphenyldichlorosilane 5, β-methylallylic alcohol 7 and Ellman sulfinimine 9.