789-25-3

Basic information

• Product Name: Triphenylsilane
• Synonyms: triphenyl-silan;SILANE, TRIPHENYL-;Triphenylsilaneminoffwhitepowder;Triphenylsilane,min.97%;Triphenysilane;Tri(phenyl)silicon;Triphenylsilane ,98%;TRIPHENYLSILANE, 99+%
• CAS NO: 789-25-3
• Molecular Formula: C₁₈H₁₆Si
• Molecular Weight: 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
• Article Data: 52

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Boiling Point: 152 °C2 mm Hg(lit.)
• Flash Point: 169 °F
• Appearance: off-white/Powder
• Refractive Index: 1.6160
• Storage Temp.: Store at
• Solubility: sol most organic solvents.
• Water Solubility: REACTS
• Sensitive: Air Sensitive
• BRN: 978182
• CAS DataBase Reference: Triphenylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylsilane(789-25-3)
• EPA Substance Registry System: Triphenylsilane(789-25-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 789-25-3(Hazardous Substances Data)

Usage

Chemical Properties

Triphenylsilane is Off-white solid

Physical properties

mp 47 °C; bp 152 °C/2 mmHg.

Uses

Different sources of media describe the Uses of 789-25-3 differently. You can refer to the following data:
1. 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.
2. 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
3. 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.

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.

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.]

InChI:InChI=1/C18H15Si/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

Upstream product

• 694-53-1 phenylsilane 
• 100-58-3 phenylmagnesium bromide 
• 60-29-7 diethyl ether 
• 108-90-7 chlorobenzene 
• 775-12-2 diphenylsilane 
• 16343-18-3 1,1,2,2-tetraphenyldisilane 
• 2875-18-5 2,3,5,6-tetrafluoropyridine 
• 98-13-5 Phenyltrichlorosilane 
• 16853-85-3 lithium aluminium tetrahydride 
• 76-86-8 Triphenylsilyl chloride 
• 15487-82-8 triphenylsilylkalium 
• 204264-94-8 Nb(η(5)-C5H4SiMe3)2(H)2(GePh3) 
• 892-20-6 triphenylstannane 
• 100-59-4 phenylmagnesium chloride 

Downstream Products

• 18750-88-4 ethyl 3-triphenylsiloxybutanoate 
• 1048-08-4 tetraphenylsilane 
• 18858-80-5 triphenyl-(toluene-4-sulfenyl)-silane 
• 18751-40-1 sec-butoxytriphenylsilane 
• 18858-69-0 (benzyloxy)triphenylsilane 
• 5410-07-1 benzyl(triphenyl)silane 
• 18754-92-2 Si,Si,Si-trimethyl-Si',Si',Si'-triphenyl-Si,Si'-propanediyl-bis-silane 
• 2117-32-0 n-butyl(triphenyl)silane 
• 6990-64-3 triphenylsilyl bromide 
• 18857-43-7 ((benzhydryloxy)triphenylsilane) 
• 18758-63-9 Triphenyl-dodecyl-silan 
• 18768-70-2 tetradecyl-triphenyl-silane 
• 17106-33-1 octyl-triphenyl-silane 
• 18848-49-2 ndecylSiPh₃ 

Relevant articles and documents

The Role of (tBuPOCOP)Ir(I) and Iridium(III) Pincer Complexes in the Catalytic Hydrogenolysis of Silyl Triflates into Hydrosilanes

Hydrosilanes are convenient reductants for a large variety of organic substrates, but they are produced via energy-intensive processes. These limitations call for the development of general catalytic processes able to transform Si-O into Si-H bonds. We report here the catalytic hydrogenolysis of R3SiOTf (R = Me, Et, and Ph) species in the presence of a base (e.g., NEt3), by the hydride complexes [(tBuPOCOP)IrH(X)] (X = H and OTf; (tBuPOCOP = [C6H3-2,6(OPtBu)2]. Syntheses and crystal structures of new iridium(I) and iridium(III) complexes are presented as well as their role in the R3SiOTf to R3SiH transformation. The mechanisms of these reactions have been examined by DFT studies, revealing that the active species involved in the reduction of the Si-OTf vs Si-Cl bond are different. The rate-determining transition state is a base-assisted splitting of H2, forming an iridium(III) dihydride species.

Organocalcium Complex-Catalyzed Selective Redistribution of ArSiH3or Ar(alkyl)SiH2to Ar3SiH or Ar2(alkyl)SiH

Calcium is an abundant, biocompatible, and environmentally friendly element. The use of organocalcium complexes as catalysts in organic synthesis has had some breakthroughs recently, but the reported reaction types remain limited. On the other hand, hydrosilanes are highly important reagents in organic and polymer syntheses, and redistribution of hydrosilanes through C-Si and Si-H bond cleavage and reformation provides a straightforward strategy to diversify the scope of such compounds. Herein, we report the synthesis and structural characterization of two calcium alkyl complexes supported by β-diketiminato-based tetradentate ligands. These two calcium alkyl complexes react with PhSiH3 to generate calcium hydrido complexes, and the stability of the hydrido complexes depends on the supporting ligands. One calcium alkyl complex efficiently catalyzes the selective redistribution of ArSiH3 or Ar(alkyl)SiH2 to Ar3SiH and SiH4 or Ar2(alkyl)SiH and alkylSiH3, respectively. More significantly, this calcium alkyl complex also catalyzes the cross-coupling between the electron-withdrawing substituted Ar(R)SiH2 and the electron-donating substituted Ar′(R)SiH2, producing ArAr′(alkyl)SiH in good yields. The synthesized ArAr′(alkyl)SiH can be readily transferred to other organosilicon compounds such as ArAr′(alkyl)SiX (where X = OH, OEt, NEt2, and CH2SiMe3). DFT investigations are carried out to shed light on the mechanistic aspects of the redistribution of Ph(Me)SiH2 to Ph2(Me)SiH and reveal the low activation barriers (17-19 kcal/mol) in the catalytic reaction.

Highly selective redistribution of primary arylsilanes to secondary arylsilanes catalyzed by Ln(CH2C6H4NMe2-: O)3@SBA-15

Rare-earth metal tris(aminobenzyl) complexes Ln(CH2C6H4NMe2-o)3 (Ln = La, Y) were grafted onto the dehydroxylated periodic mesoporous silica support SBA-15 to generate the organometallic-inorganic hybrid materials Ln(CH2C6H4NMe2-o)3@SBA-15 (Ln = La (2a), Y (2b)), which demonstrated extremely high selectivity (>99%) in catalyzing the redistribution of primary arylsilanes to secondary arylsilanes without the requisition of strict control of the reaction conditions. The hybrid materials still showed a perfect selectivity and activity after three catalytic cycles.