Triphenylsilane Chemical Properties

Melting point:

43-45 °C (lit.)

Boiling point:

152 °C/2 mmHg (lit.)

refractive index 

1.6160

Flash point:

169 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

sol most organic solvents.

form 

Powder

color 

off-white

Water Solubility 

REACTS

Sensitive 

Air Sensitive

Hydrolytic Sensitivity

3: reacts with aqueous base

BRN 

978182

InChIKey

AKQNYQDSIDKVJZ-UHFFFAOYSA-N

CAS DataBase Reference

789-25-3(CAS DataBase Reference)

NIST Chemistry Reference

Silane, triphenyl-(789-25-3)

EPA Substance Registry System

Silane, triphenyl- (789-25-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

WGK Germany 

1

TSCA 

Yes

HS Code 

29310095

MSDS

• Language:English Provider:Triphenylsilane
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Triphenylsilane Usage And Synthesis

Chemical Properties

Triphenylsilane is an off-white solid that is soluble in most organic solvents. It is used in certain cases for the preparation of triphenylsilyl ethers, which serve as alcohol-protecting groups. The triphenylsilyl group is considerably more stable (about 400 times) than the TMS group toward acidic hydrolysis.

Uses

Triphenylsilane acts as a reactant or reagent for catalytic hydrogen deuterium exchange reactions of silanes, to be oxidized by carbon nanotube-gold nanohybrids, for hydrolysis by ruthenium complexes, for hydrosilylation to produce enolsilanes, for synthesis of bromosilanes, for ozone oxidation of silyl-alkenes for synthesis of α-O-silylated acyloin derivatives. It is used to synthesize hydrido silyl and bis(silyl) bis(imidazolinylidene) nickel complexes.

Preparation

Triphenylsilane can be synthesized by reducing phenylsilane (PhSiH3) with a reducing agent such as lithium aluminum hydride (LiAlH4). The overall reaction equation is as follows:
3 PhSiH3 + 2 LiAlH4 → C18H16Si + 2 LiH + 2 AlH3
This reaction is typically carried out in anhydrous conditions and under inert gas atmosphere.

Application

More effective radical-based reagent for reduction of organic halides than the trialkylsilanes.
Compares well with tri-n-butyltin hydride in reduction of enones to ketones.
Shows good selectivity in the reduction of cyclic hemiacetals.
Converts O-acetyl furanoses and pyranoses to deoxy sugars.
Hexaphenyldisiloxane can be conveniently made by the action of aqueous alkali on triphenylsilane, Ph3SiH.
Tristriphenylsilylbismuth, (Ph3Si)3Bi, is made similarly from triethylbismuth and triphenylsilane: Et3Bi+3Ph3SiH==Heat==(Ph3Si)3Bi+3EtH.

storage

This reagent is stable in the air. Because the toxicogical properties are unknown, it should be handled in a well-ventilated fume hood. Contact with the eyes and skin should be avoided.

Purification Methods

Purify it by recrystallisation from MeOH. [Gilman & Zuech J Am Chem Soc 81 5925 1959, Westermark Acta Chem Scand 9 947 1955, IR: Kaplan J Am Chem Soc 76 5880 1954, Beilstein 16 II 605, 16 III 1199, 16 IV 1369.]

Triphenylsilane(789-25-3)Related Product Information

• Phenyltrichlorosilane
• Chlorodimethylphenylsilane
• Dichlorodiphenylsilane
• Diphenyldimethoxysilane
• Triethylsilane
• Diphenylsilane
• Phenyltriethoxysilane
• Triphenylphosphine
• Triphenylsilyl chloride
• Triphenylmethyl Chloride
• TRIPHENYLVINYLSILANE
• HEXAPHENYLDISILANE
• METHYLTRIPHENYLSILANE
• TRIPHENYLETHOXYSILANE
• Oxybis(triphenylsilane)
• Tetraphenylsilane
• 1,2,2-Trifluorovinyl-triphenylsilane,1,2,2-Trifluoroethenyl-triphenylsilane
• Triphenylsilanol