Triphenylsilane

Base Information

• Chemical Name: Triphenylsilane
• CAS No.: 789-25-3
• Molecular Formula: C18H16Si
• Molecular Weight: 260.411
• Hs Code.: 29310095
• European Community (EC) Number: 212-333-0
• UNII: UQL9QY2CS8
• DSSTox Substance ID: DTXSID10883583
• Nikkaji Number: J364.241K
• Wikidata: Q20850936
• Mol file: 789-25-3.mol

Synonyms:Triphenylsilane;triphenylhydrosilane;Benzene, 1,1',1''-silylidynetris-;Triphenylsilane, 97%;NSC 12565;UQL9QY2CS8;C18H16Si;EINECS 212-333-0;triphenylsilicon;Triphenylsilyl radical;UNII-UQL9QY2CS8;C18-H16-Si;DTXSID10883583;1,1',1''-Silylidynetrisbenzene;AMY42285;AKOS008901160;AKOS015907204;PB47734;AS-14886;1,1',1''-SILYLIDYNETRIS(BENZENE);CS-0156585;FT-0632957;T0661;S20600;EN300-7425612;A839533;J-525126;Q20850936

Chemical Property of Triphenylsilane

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 43-45 °C(lit.)
• Refractive Index: 1.6160
• Boiling Point: 347.1 °C at 760 mmHg
• Flash Point: 156.1 °C
• PSA: 0.00000
• LogP: 1.93510
• Storage Temp.: Store at
• Sensitive.: Air Sensitive
• Solubility.: sol most organic solvents.
• Water Solubility.: REACTS
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 259.094302013
• Heavy Atom Count: 19
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Triphenylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C1=CC=C(C=C1)[Si](C2=CC=CC=C2)C3=CC=CC=C3
• Physical properties: mp 47 °C; bp 152 °C/2 mmHg.
• 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. Reactant or reagent:? ;For catalytic hydrogen deuterium exchange reactions of silanes1? ;To be oxidized by carbon nanotube-gold nanohybrids2? ;For hydrolysis by ruthenium complexes3? ;For hydrosilylation to produce enolsilanes4? ;For synthesis of bromosilanes5? ;For ozone oxidation of silyl-alkenes for synthesis of α-O-silylated acyloin derivatives6? ;Used to synthesize hydrido silyl and bis(silyl) bis(imidazolinylidene) nickel complexes7 Triphenylsilane is reducing agent for esters, xanthates, and polychloroalkanes; protecting group for alcohols. It takes part in the reactions of Deoxygenations, Hydrosilylations, Lewis Acid-assisted Hydrosilylations, Heteroatom Reductions, Multiple Bond Reductions, Alkene Hydrogenations, Silylations, etc.

Technology Process of Triphenylsilane

There total 83 articles about Triphenylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

methoxy-triphenyl-silane (1829-41-0) → HSiPh3 (789-25-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; ethyl bromide; tetraoctyl ammonium bromide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1039/c9cc01961h

Reference yield: 88.0%

trichlorosilane (10025-78-2) → HSiPh3 (789-25-3)

Guidance literature:

With phenylmagnesium bromide; In diethyl ether; HSiCl3 and C6H5MgBr in ether; boiling for a longer period of time;;

DOI:10.1021/ja01180a051

Reference yield: 88.0%

diphenylsilane (775-12-2) + phenyllithium (591-51-5) → HSiPh3 (789-25-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; diethyl ether; at 25 ℃; for 0.00833333h; Flow reactor; Green chemistry;

DOI:10.1039/d0gc03213a

upstream raw materials:

Triphenylsilyl chloride

diphenylsilane

octaphenylcyclotetrasilane

silatrane

Downstream raw materials:

ethyl 3-triphenylsiloxybutanoate

tetraphenylsilane

triphenyl-o-tolyloxy-silane

triphenyl-(toluene-4-sulfenyl)-silane

Refernces

• 1、 Corriu, R.J.P.,Guerin, C.,Henner, B.J.L.,Wang, Q.. "Hydride transfer reactions between penta- and tetra-coordinate silicon derivatives". . p. C1 - C5. Retrieved 1992.
• 2、 Lee, Hyune-Jea,Kwak, Changmo,Kim, Dong-Pyo,Kim, Heejin. "Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide". supporting information. p. 1193 - 1199. Retrieved 2021/02/26.
• 3、 Comas-Vives, Aleix,Eiler, Frederik,Grützmacher, Hansj?rg,Pribanic, Bruno,Trincado, Monica,Vogt, Matthias. "Hydrogenolysis of Polysilanes Catalyzed by Low-Valent Nickel Complexes". supporting information. p. 15603 - 15609. Retrieved 2020/04/29.