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Triphenylsilane

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Triphenylsilane Basic information

Product Name:
Triphenylsilane
Synonyms:
  • triphenyl-silan
  • Triphenylhydrosilane
  • Triphenylsilaneminoffwhitepowder
  • Triphenylsilane,min.97%
  • Triphenysilane
  • SILANE, TRIPHENYL-
  • TRIPHENYLSILANE FOR SYNTHESIS
  • Tri(phenyl)silicon
CAS:
789-25-3
MF:
C18H16Si
MW:
260.41
EINECS:
212-333-0
Product Categories:
  • Silane compounds
  • Reduction
  • Si (Classes of Silicon Compounds)
  • Si-H Compounds
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Phenyl Silanes
  • Organometallic Reagents
  • Organosilicon
  • OthersSynthetic Reagents
  • Silanes
  • organosilicon compounds
  • Chemical Synthesis
  • Organometallic Reagents
  • Others
  • Synthetic Reagents
Mol File:
789-25-3.mol
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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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37
WGK Germany 
1
TSCA 
Yes
HS Code 
29310095

MSDS

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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.

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.]

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