Triphenylsilane Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

WGK Germany 

1

TSCA 

Yes

HS Code 

29310095

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Triphenylsilane Chemical Properties,Usage,Production

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.]