791-31-1

Basic information

• Product Name: Triphenylsilanol
• Synonyms: TRIPHENYLSILANOL;hydroxytriphenyl-silan;Silane, (hydroxytriphenyl)-;Silanol,triphenyl-;Triphenylhydroxysilane;triphenyl-silano;Triphenylsilylhydroxide;Triphenylsilanolwhitepowder
• CAS NO: 791-31-1
• Molecular Formula: C₁₈H₁₆OSi
• Molecular Weight: 276.4
• EINECS: 212-339-3
• Product Categories: Si (Classes of Silicon Compounds);Silanols;Si-O Compounds;Phenyl Silanes;organosilicon compound
• Mol File: 791-31-1.mol
• Article Data: 95

Chemical Properties

• Melting Point: 150-153 °C(lit.)
• Boiling Point: 389 °C [760mmHg]
• Flash Point: >200°C
• Appearance: white/Powder
• Density: 1.13
• Vapor Pressure: 9.79E-07mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Store below +30°C.
• PKA: 13.39±0.58(Predicted)
• Water Solubility: reacts
• Sensitive: Air Sensitive
• BRN: 985007
• CAS DataBase Reference: Triphenylsilanol(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylsilanol(791-31-1)
• EPA Substance Registry System: Triphenylsilanol(791-31-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• RTECS: VV4325500
• F: 21
• TSCA: Yes
• Hazardous Substances Data: 791-31-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

Uses

Triphenylsilanol is used as a water surrogate for regioselective Pd catalyzed allylations. A thick on germanium substrates have been produced by the electron bombardment of an evaporated thin film of triphenylsilanol.

Definition

ChEBI: An organosilanol in which silicon is bonded to a single hydroxy function and to three phenyl groups.

Purification Methods

It is purified by dissolving in pet ether, passing through an Al2O3 column, eluting thoroughly with CCl4 to remove impurities and then eluting the silanol with MeOH. Evaporation gives crystals with m 153-155o. It can be recrystallised from pet ether, CCl4 or from *benzene or Et2O/pet ether (1:1). It has also been recrystallised by partial freezing from the melt to constant melting point. [George & Gilman J Am Chem Soc 81 3288 1959, IR: Tatlock & Rochow J Org Chem 17 1555 1952 and Richards & Thompson J Chem Soc 124 1949, Beilstein 16 IV 1480.]

InChI:InChI=1/C18H16OSi/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H

Synthetic route

HSiPh3 (789-25-3) → triphenylhydroxysilane (791-31-1)

Conditions	Yield
With water In acetone at 20℃; for 5h;	99%
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; tert-butyl alcohol for 0.5h; Time; Green chemistry;	99%
With water at 20℃; for 2.83333h;	99%

tris(triphenylsiloxy)iron → triphenylhydroxysilane (791-31-1)

Conditions	Yield
With H2O; HCl In water; acetone stirring (room temp., 5 min); evapn. in air, extn. (CCl4, 70°C), pptn. on evapn.; IR spectroscopy;	99%

9H2O*6C4H12N(1+)*H(1+)*Sb5Mo18O66(7-) + HSiPh3 (789-25-3) → triphenylhydroxysilane (791-31-1)

Conditions	Yield
With tert.-butylhydroperoxide In acetonitrile at 50℃; for 12h;	98.3%

HSiPh3 (789-25-3) → hydrogen (1333-74-0) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With water In acetone at 25℃; for 6h; Catalytic behavior; Mechanism;	A n/a B 98%
With water; silver nitrate at 24.84℃; for 0.5h;	A 45% B 49%

sodium triphenylsilanolate (16527-35-8) → triphenylhydroxysilane (791-31-1)

Conditions	Yield
With CH3COOH In acetic acid	97%

ethoxy(triphenylsilyl)keten → triphenylhydroxysilane (791-31-1) + W(CO)6

Conditions	Yield
With (CO)5WC(OEt)SiPh3 In diethyl ether at 80 - 100℃; for 1h; Product distribution;	A 96% B n/a

(CO)5WC(OEt)SiPh3 → tungsten hexacarbonyl (14040-11-0) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 96%
With carbon monoxide In pentane High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 96%

(CO)5CrC(OEt)SiPh3 → chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 96%
With carbon monoxide In pentane High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 96%

(CO)5MoC(OEt)SiPh3 → molybdenum hexacarbonyl (13939-06-5, 199620-15-0) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 96%
With carbon monoxide In pentane High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 96%

hexaphenyldisilane (1450-23-3) → triphenylhydroxysilane (791-31-1)

Conditions	Yield
With 1% Au/TiO2; water In ethyl acetate at 55℃; for 5h;	92%

(CO)5WC(OEt)SiPh3 + benzylidene phenylamine (538-51-2) → tungsten hexacarbonyl (14040-11-0) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(C6H5) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(C6H5) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B n/a C n/a D 90%

(CO)5CrC(OEt)SiPh3 + benzylidene phenylamine (538-51-2) → CH(C6H5)CSi(C6H5)3(C2H5O)CON(C6H5) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(C6H5) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A 74% B 16% C n/a D 90%

(CO)5MoC(OEt)SiPh3 + benzylidene phenylamine (538-51-2) → CH(C6H5)CSi(C6H5)3(C2H5O)CON(C6H5) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(C6H5) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B n/a C n/a D 90%

(benzyloxy)triphenylsilane (18858-69-0) → toluene (108-88-3) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With palladium on activated charcoal; hydrogen In tetrahydrofuran-d8 at 20℃; under 760.051 Torr; for 1.5h; Reagent/catalyst; Solvent;	A n/a B 90%

triphenylsilyl lithium + mercury dibromide → hexaphenyldisiloxanne (1829-40-9) + hexaphenyldisilane (1450-23-3) + mercury + triphenylhydroxysilane (791-31-1)

Conditions	Yield
In tetrahydrofuran at -70°C; 2mol (C6H5)3SiLi;;	A 11.2% B 50.3% C 77.5% D 33.3%
In tetrahydrofuran at -70°C; 2mol (C6H5)3SiLi;;	A 11.2% B 50.3% C 77.5% D 33.3%

Acetyltriphenylsilane (4916-42-1) + 1-phenyl-5-((3-phenylpropyl)sulfonyl)-1H-tetrazole → 5-phenyl-2-pentanone (2235-83-8) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
Stage #1: Acetyltriphenylsilane; 1-phenyl-5-((3-phenylpropyl)sulfonyl)-1H-tetrazole With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Brook rearrangement; Stage #2: With water In tetrahydrofuran	A 75% B n/a

bis(triphenylsiloxy)cobalt → triphenylhydroxysilane (791-31-1)

Conditions	Yield
With H2O In water; acetone stirring (room temp., 5 min); evapn. in air, extn. (CCl4, 70°C), pptn. on evapn.; IR spectroscopy;	75%

(CO)5WC(OEt)SiPh3 + N-Benzylidenemethylamine (622-29-7) → tungsten hexacarbonyl (14040-11-0) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(CH3) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(CH3) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A n/a B 74% C 16% D 5%

(CO)5CrC(OEt)SiPh3 + N-Benzylidenemethylamine (622-29-7) → CH(C6H5)CSi(C6H5)3(C2H5O)CON(CH3) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(CH3) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A 74% B 16% C n/a D 5%

(CO)5MoC(OEt)SiPh3 + N-Benzylidenemethylamine (622-29-7) → CH(C6H5)CSi(C6H5)3(C2H5O)CON(CH3) + CH(C6H5)CSi(C6H5)3(C2H5O)CON(CH3) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With carbon monoxide In diethyl ether High Pressure; under dried N2; addn. of N-methylbenzimine at 25°C to a soln. of W-complex (CO-pressure: 50 atm); stirring for 2 d at room temp., then for 1-2 h at 80-100°C; vac.-evapn. until dryness; residue dissolved in petroleum ether/ether; chromy. (silica gel/petroleum ether/ether); recrystn. from petroleum ether; elem. anal.;	A 74% B 16% C n/a D 5%

allyltriphenylsilane (18752-21-1) → (E)-diphenyl-1-propenylsilanol + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at -45 - 20℃;	A 71% B 19%
With 18-crown-6 ether; potassium tert-butylate; dimethyl sulfoxide In tetrahydrofuran at -45 - 20℃;	A 71% B 19%
With 18-crown-6 ether; potassium tert-butylate; dimethyl sulfoxide at 20℃; for 0.333333h;	A 23% B 70%

1-propenyl(triphenyl)silane (18752-22-2) → (E)-diphenyl-1-propenylsilanol + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate; dimethyl sulfoxide at 20℃; for 0.333333h;	A 68% B 26%

dimethyl(phenyl)silyllithium (3839-31-4) + triphenylsilyl tris(trimethylsilyl)silanecarboxylate (81671-48-9) → Tris-(trimethylsilyl)-silancarbonsaeure (70096-33-2) + 2,2-dimethyl-2-phenyltris(trimethylsilyl)disilane (197797-30-1) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With water In tetrahydrofuran for 20h;	A 10% B 64% C 61%

phenyllithium (591-51-5) + triphenylsilyl tris(trimethylsilyl)silanecarboxylate (81671-48-9) → 2,2-dimethyl-2-phenyltris(trimethylsilyl)disilane (197797-30-1) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With water In tetrahydrofuran	A n/a B 61%

p-chlorphenylisocyanate (104-12-1) + 3-Diethylamino-2-<1-(triphenylsiloxy)vinyl>-2-cyclobuten-1-on (79139-28-9) → 2-Acetyl-3-(diethylamino)-2-cyclobuten-1-on (73000-93-8) + 4'-Chlor-3-<2-(diethylamino)-4-oxo-1-cyclobutenyl>-3-oxopropananilid (79139-27-8) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
In acetonitrile for 144h; Ambient temperature;	A 60% B 30% C 58%

3-Diethylamino-2-<1-(triphenylsiloxy)vinyl>-2-cyclobuten-1-on (79139-28-9) → 2-Acetyl-3-(diethylamino)-2-cyclobuten-1-on (73000-93-8) + 4'-Chlor-3-<2-(diethylamino)-4-oxo-1-cyclobutenyl>-3-oxopropananilid (79139-27-8) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With p-chlorphenylisocyanate In acetonitrile for 144h; Ambient temperature;	A 60% B 30% C 58%
With p-chlorphenylisocyanate In acetonitrile for 144h; Ambient temperature; further reagent: m-chloroperbenzoic acid;	A 60% B 30% C 58%

tris(trimethylsilyl)silyllithium (4110-02-5) + triphenylsilyl tris(trimethylsilyl)silanecarboxylate (81671-48-9) → tetrakis(trimethylsilyl)silane (4098-98-0) + Tris-(trimethylsilyl)-silancarbonsaeure (70096-33-2) + Si(SiMe3)3(SiPh3) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With water In tetrahydrofuran	A 19% B 58% C 46% D 37%

C26H30Si (1277099-83-8) → C26H30O3Si (1277099-84-9) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With oxygen; ozone In ethyl acetate at -78℃;	A 9% B 58%

1-fluorovinyl 2-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate + 4-methoxy-aniline (104-94-9) → triphenylsilyl fluoride (379-50-0) + 4-methoxyacetanilide (51-66-1) + 3-benzyltetrahydrofuran-2-one (68975-07-5, 68975-13-3, 68975-14-4, 61129-28-0) + triphenylhydroxysilane (791-31-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	A 40% B 57% C 30% D 46%

triphenylhydroxysilane (791-31-1) → triphenylsilyl fluoride (379-50-0)

Conditions	Yield
With hydrogen fluoride In methanol for 0.5h; Ambient temperature;	100%
With hydrogen fluoride In methanol at 20℃; for 0.5h; Substitution;	95%
With ethanol; hydrogen fluoride; water
With HF In hydrogen fluoride aq. HF; (C6H5)3SiOH and 48% aq. HF;;	>99
With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

salicylic alcohol (90-01-7) + boric acid (11113-50-1) + triphenylhydroxysilane (791-31-1) → 2-triphenylsiloxy-4H-1,3,2-benzodioxaborin (82172-56-3)

Conditions	Yield
In benzene byproducts: H2O; azeotropic removal of water; elem. anal.;	100%

boric acid (11113-50-1) + benzene-1,2-diol (120-80-9) + triphenylhydroxysilane (791-31-1) → 2-triphenylsiloxy-1,3,2-benzodioxaborole (82172-55-2)

Conditions	Yield
In benzene byproducts: H2O; azeotropic removal of water; elem. anal.;	100%

boric acid (11113-50-1) + ethylene glycol (107-21-1) + triphenylhydroxysilane (791-31-1) → 2-triphenylsiloxy-1,3,2-dioxaborolane (82172-50-7)

Conditions	Yield
In benzene byproducts: H2O; azeotropic removal of water; distd. in vac., elem. anal.;	100%

trimethylaluminum (75-24-1) + triphenylhydroxysilane (791-31-1) → C58H53AlO4Si3 (143607-50-5)

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran; hexane byproducts: methane; (dry N2); dropwise addn. of AlMe3 hexane soln. to a stirred soln. of 3 equiv. of HOSiPh3 in THF at 0°C, stirring (12 h); removal of volatiles in vac.;	99.9%

tetrabenzylzirconium(IV) (24356-01-2) + triphenylhydroxysilane (791-31-1) → tetrakis(triphenylsilanolato)zirconium

Conditions	Yield
In benzene silanol reacted with Zr compd. (0.5 equiv.) in benzene;	99%

[Re(neopentyl)2(neopentylidene)(neopentylydine)] (86823-35-0) + triphenylhydroxysilane (791-31-1) → [Re(neopentyl)(OSiPh3)(neopentylidene)(neopentylidyne)]

Conditions	Yield
In benzene byproducts: t-BuCH3; benzene, 1 equiv of silanol, room temp.;	99%
In benzene-d6 byproducts: neopentane; (Ar); using Schlenk techniques; addn. of 1 equiv. of Ph3SiOH to soln. ofRe(C(t-Bu))(CH(t-Bu))(CH2(t-Bu))2 in C6D6 in NMR tube; holding at room temp. for 12 h; monitoring by NMR; evapn., as inseperable mixt. of syn and anti rotamersin 10/1 ratio; as oil;

(tetrahydrofuran)[trans-1,2-bis(2,4,6-triisopropylbenzenesulfonamidato)cyclohexane-N,N'][bis(dimethylsilyl)amido]yttrium(III) + triphenylhydroxysilane (791-31-1) → Y(C4H8O)(OSi(C6H5)3)(C36H56N2O4S2)*C7H8

Conditions	Yield
In toluene (argon); stirring (room temp., 12 h); removal of volatiles (vac.), recrystn. (hot toluene); elem. anal.;	99%

diisopropoxidobis(2,4-pentanedionato)zirconium(IV) + triphenylhydroxysilane (791-31-1) → zirconium (triphenylsilanolat)2-bis(acetylacetonate)

Conditions	Yield
In benzene byproducts: (CH3)2CHOH; performed in a moisture free environment; benzene soln. of Zr(acac)2(OiPr)2 added to a benzene suspension of the organic ligand; refluxed for 4h; solvent removed under reduced pressure; purified by recrystallization from a mixture of dichloromethane and n-hexane; elem. anal.;	99%

methoxy(diphenyl)pyrrolidinosilane (1384834-55-2) + triphenylhydroxysilane (791-31-1) → 1-methoxy-1,1,3,3,3-pentaphenyldisiloxane (1384834-60-9)

Conditions	Yield
In diethyl ether at 20℃; for 30h;	99%

Zr(η5-cyclopentadienyl)3(η1-cyclopentadienyl) + triphenylhydroxysilane (791-31-1) → bis(η5-cyclopentadienyl)bis(triphenylsiloxy)zirconium(IV)

Conditions	Yield
In toluene byproducts: CpH; Ar-atmosphere; stirring Zr-complex with 2 equiv. of Si-compd. (room temp., 5 h); evapn. (after 15 h, reduced pressure, room temp.), addn. of heptane, filtration, washing (heptane), drying (vac.);	98%
In toluene byproducts: CpH; Ar-atmosphere; stirring Zr-complex with 1 equiv. of Si-compd. (room temp., 5 h); evapn. (after 15 h, reduced pressure, room temp.), addn. of heptane, filtration, washing (heptane), drying (vac.);	41%

[Li(C4H8O)2(AlH3(C(Si(CH3)3)3))]2 + triphenylhydroxysilane (791-31-1) → [Al(OSiPh3)2(C(SiMe3)3)(thf)] (502188-76-3)

Conditions	Yield
In toluene under Ar; soln. of Ph3SiOH in toluene added to soln. of Al complex in toluene at 0°C under stirring, mixt. allowed to warm to room temp.,stirred for 18 h; filtered, filtrate evapd., residue recrystd. from heptane-toluene (1:1);elem. anal.;	98%

(2,4-tert-butyl-6-([(2'-dimethylaminoethyl)methylamino]methyl)phenolate)ZnEt (613688-14-5) + triphenylhydroxysilane (791-31-1) → (2-tert-butyl-4-methoxy-6-{[(2'-dimethylaminoethyl)-methylamino]methyl}phenol-H)ZnSiOPh3 (1570188-83-8)

Conditions	Yield
In toluene at 24.84℃; for 16h; Inert atmosphere;	98%

acridine orange (494-38-2) + triphenylhydroxysilane (791-31-1) → triphenylsilanol-acridine orange salt

Conditions	Yield
In 1,4-dioxane at 20℃; for 0.25h;	98%

tris(pentafluorophenyl)borate (1109-15-5) + N,N-diethylaniline (91-66-7) + triphenylhydroxysilane (791-31-1) → C36H15BF15OSi(1-)*C10H15N*H(1+)

Conditions	Yield
In toluene at 20℃; for 2h;	97%

[Me3SiFlSi]4O12[TiO(i)Pr]4 (293329-43-8) + triphenylhydroxysilane (791-31-1) → [Me3SiFlSi]4O12[TiOSiPh3]4

Conditions	Yield
In tetrahydrofuran under Ar atm. at 0°C HOSiPh3 was added dropwise to soln. (Me3SiFlSi)4O12(TiOiPr)4 in THF and stirred for 16 h; volatiles were removed in vacuo, recrystn. from hexane; elem. anal.;	97%

ethyl trimethylsilyl ether (1825-62-3) + triphenylhydroxysilane (791-31-1) → 1,1,1-trimethyl-3,3,3-triphenyl-disiloxane (799-53-1)

Conditions	Yield
	96.5%
	96.5%
	96.5%
With hydrogenchloride

(((CH3)3C)2(O)C6H2CHNCH2)2Al(CH3) + triphenylhydroxysilane (791-31-1) → ((((CH3)3C)2(O)C6H2CHNCH2)2)Al(OSi(C6H5)3) (190370-43-5)

Conditions	Yield
In toluene inert atmosphere; stirring (25°C, 2 h ); filtering,;	96%

Cyclohexyl isocyanide (931-53-3) + dimethyl acetylenedicarboxylate (762-42-5) + triphenylhydroxysilane (791-31-1) → dimethyl 2-((cyclohexylimino)methylene)-3-(triphenylsilyloxy)succinate (1344030-61-0)

Conditions	Yield
In dichloromethane at 20℃; for 8h;	96%

[C4H2N(2,5-CH2NMe2)2AlH2] (377726-64-2) + triphenylhydroxysilane (791-31-1) → [C4H2N(2,5-CH2NMe2)2Al(OSiPh3)2] (1341127-38-5)

Conditions	Yield
In dichloromethane N2; DCM soln. of ligand added dropwise to DCM soln. of Al compd. (2:1 molar ratio), mixt. stirred at room temp. for 12 h; evapd. (vac.), recrystd. (DCM);	96%

Upstream product

• 20786-96-3 hexabromo disiloxane 
• 130969-92-5 octabromo trisiloxane 
• 694-53-1 phenylsilane 
• 538-51-2 benzylidene phenylamine 
• 1516-80-9 ethoxytriphenylsilane 
• 16527-35-8 sodium triphenylsilanolate 
• 379-50-0 triphenylsilyl fluoride 
• 15487-82-8 triphenylsilylkalium 
• 1829-40-9 hexaphenyldisiloxanne 
• 4916-42-1 Acetyltriphenylsilane 
• 123-91-1 1,4-dioxane 
• 18740-94-8 triphenyl-[2]thienyl-silane 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 

Downstream Products

• 15243-33-1 dodecacarbonyl-triangulo-triruthenium 
• 76-86-8 Triphenylsilyl chloride 
• 72207-47-7 (C₄H₉N)2((C₆H₅)3SiO)2W 
• 17964-41-9 n-butyldiphenylsilyl alcohol 
• 789-25-3 HSiPh₃ 
• 1048-08-4 tetraphenylsilane 
• 6026-51-3 (triphenylsilanolato)titanatrane 
• 88076-36-2 1-(dichloromethyl)germatrane 
• 72453-82-8 1-(triphenylsiloxy)germatrane 
• 82172-53-0 2-triphenylsiloxy-6-methyl-1,3,2-dioxaborinane 
• 82172-56-3 2-triphenylsiloxy-4H-1,3,2-benzodioxaborin 
• 82172-55-2 2-triphenylsiloxy-1,3,2-benzodioxaborole 
• 82172-54-1 triphenyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane 
• 82172-50-7 2-triphenylsiloxy-1,3,2-dioxaborolane 

Relevant articles and documents

Reactions of carboxamides with vinylsilanes under oxidative conditions

The reactions of acetamide, benzamide and trifluoroacetamide with trimethyl(vinyl)-, triphenyl(vinyl)-, dimethyl(divinyl)- and diphenyl(divinyl)silanes in the presence of oxidants (t-BuOCl + NaI) or N-bromosuccinimide (NBS) in acetonitrile have been studied. Generally, all unsaturated silanes react with trifluoroacetamide to give the products of haloamidation, whereas with acetamide or benzamide the reaction affords mainly the products of halogenation. The formation of bromoamination product containing the MeCONH moiety in the NBS-induced reaction of trimethylvinylsilane with all studied amides clearly indicates that the reaction proceeds with the solvent (MeCN) interception rather than by the attack of the amide nucleophile. The product of bromoamidation from the NBS-promoted reaction undergoes a base-induced cyclization to the corresponding 1,3-oxazoline in quantitative yield.

Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis

A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers, respectively, in moderate to excellent yields. The dehydrogenative cross-coupling of Si-H and O-H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirement of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cationviavisible-light photoredox catalysis.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.