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Triphenylsilane

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CAS:789-25-3
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  • 2019-07-06
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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
Triphenylsilane Structure
Triphenylsilane Chemical Properties
Melting point 43-45 °C (lit.)
Boiling point 152 °C/2 mmHg (lit.)
refractive index 1.6160
Fp 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 Sensitivity3: reacts with aqueous base
BRN 978182
InChI1S/C18H16Si/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
InChIKeyAKQNYQDSIDKVJZ-UHFFFAOYSA-N
SMILESc1ccc(cc1)[SiH](c2ccccc2)c3ccccc3
CAS DataBase Reference789-25-3(CAS DataBase Reference)
NIST Chemistry ReferenceSilane, triphenyl-(789-25-3)
EPA Substance Registry SystemSilane, triphenyl- (789-25-3)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37
WGK Germany 1
TSCA TSCA listed
HS Code 29310095
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
MSDS Information
ProviderLanguage
Triphenylsilane English
SigmaAldrich English
ACROS English
ALFA English
Triphenylsilane Usage And Synthesis
Chemical PropertiesTriphenylsilane 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.
UsesTriphenylsilane 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.
ApplicationMore 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.
PreparationTriphenylsilane 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.
reaction suitabilityreagent type: reductant
storageThis 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 MethodsPurify 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.]
Tag: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

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