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76-86-8

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76-86-8 Usage

?Acute toxicity

IV- mouse LD50: 56 mg/kg

Description

Triphenylsilyl chloride is a white to off-white crystal or powder with acrid ordor of hydrogen chloride, used for synthesis of pharmaceutical intermediates.

Physical properties

mp 92–94°C; bp 240–243°C/35 mmHg.

Uses

Different sources of media describe the Uses of 76-86-8 differently. You can refer to the following data:
1. A wide variety of Grignard reagents and organolithium complexes participate in reactions with Ph3SiCl to afford organosilanes. Thus the reaction of allylmagnesium chloride with Ph3SiCl gives the allylsilane in high yield (eq 3).However, when hydrosilyl Grignard reagents are employed, reduction to the silane occurs (eq 4).Azaallyl anion6 and diazolithium salts can each be silylated to give the anticipated silane adducts (eqs 5 and 6). Similarly, arylsilanes8 and alkynylsilanes are produced upon silylation of the appropriate metalated13 carbanions with Ph3SiCl (eqs 7–11).
2. Chlorotriphenylsilane is used as a silylating agent. It is also used as a pharmaceutical intermediate.

Purification Methods

Likely impurities are tetraphenylsilane, small amounts of hexaphenyldisiloxane and traces of triphenylsilanol. Purify it by distillation at 2mm, then crystallise it from EtOH-free CHCl3, and from pet ether (b 30-60o) or hexane by cooling in a Dry-ice/acetone bath. [Allen & Modena J Chem Soc 3671 1957, Curran et al. J Am Chem Soc 72 4471 1950, Speier & Zimmerman J Am Chem Soc 77 6395 1955, Thomas & Rochow J Am Chem Soc 79 1843 1957, Beilstein 16 IV 1484.]

Check Digit Verification of cas no

The CAS Registry Mumber 76-86-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 76-86:
(4*7)+(3*6)+(2*8)+(1*6)=68
68 % 10 = 8
So 76-86-8 is a valid CAS Registry Number.
InChI:InChI=1/C18H15ClSi/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

76-86-8 Well-known Company Product Price

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  • TCI America

  • (T0939)  Triphenylchlorosilane  >95.0%(GC)

  • 76-86-8

  • 5g

  • 150.00CNY

  • Detail
  • TCI America

  • (T0939)  Triphenylchlorosilane  >95.0%(GC)

  • 76-86-8

  • 25g

  • 450.00CNY

  • Detail
  • Alfa Aesar

  • (A13678)  Chlorotriphenylsilane, 96%   

  • 76-86-8

  • 5g

  • 230.0CNY

  • Detail
  • Alfa Aesar

  • (A13678)  Chlorotriphenylsilane, 96%   

  • 76-86-8

  • 25g

  • 864.0CNY

  • Detail
  • Alfa Aesar

  • (A13678)  Chlorotriphenylsilane, 96%   

  • 76-86-8

  • 50g

  • 1590.0CNY

  • Detail
  • Alfa Aesar

  • (A13678)  Chlorotriphenylsilane, 96%   

  • 76-86-8

  • 100g

  • 3023.0CNY

  • Detail
  • Aldrich

  • (114162)  Chlorotriphenylsilane  96%

  • 76-86-8

  • 114162-5G

  • 253.89CNY

  • Detail
  • Aldrich

  • (114162)  Chlorotriphenylsilane  96%

  • 76-86-8

  • 114162-25G

  • 948.87CNY

  • Detail

76-86-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Chlorotriphenylsilane

1.2 Other means of identification

Product number -
Other names Silane, chlorotriphenyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:76-86-8 SDS

76-86-8Synthetic route

HSiPh3
789-25-3

HSiPh3

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With hexachloroethane; palladium dichloride at 20℃; for 1h;100%
With dichloromethane; eosin y at 40℃; Temperature; Reagent/catalyst; Flow reactor; Inert atmosphere; Irradiation; Green chemistry;99%
With trichloroisocyanuric acid In dichloromethane Heating;97.5%
tetrachlorosilane
10026-04-7, 53609-55-5

tetrachlorosilane

phenyllithium
591-51-5

phenyllithium

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
In not given SiCl4 and C6H5Li (mol. ratio 1:3);;99%
In not given SiCl4 and C6H5Li (mol. ratio 1:3);;99%
(chloromethyl)trichlorosilane
1558-25-4

(chloromethyl)trichlorosilane

HSiPh3
789-25-3

HSiPh3

A

Methyltrichlorosilane
75-79-6

Methyltrichlorosilane

B

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
at 165 - 250℃; for 12h;A 87.3%
B 95.8%
at 165 - 210℃; for 12h;A 95.8%
B 87.3%
triphenylhydroxysilane
791-31-1

triphenylhydroxysilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether introduction of gaseous HCl into a soln. of (C6H5)3SiOH in abs. ether at room temp.;;90%
With HCl In diethyl ether introduction of gaseous HCl into a soln. of (C6H5)3SiOH in abs. ether at room temp.;;90%
With iron(III) chloride; acetyl chloride In 1,2-dichloro-ethane for 2h;57%
methoxy-triphenyl-silane
1829-41-0

methoxy-triphenyl-silane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With iron(III) chloride; acetyl chloride In 1,2-dichloro-ethane for 24h;90%
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With bis(tricyclohexylphosphine)nickel(II) dichloride; triethylaluminum; dimethylaluminum chloride In 1,4-dioxane; hexane; 1,3,5-trimethyl-benzene at 90℃; for 0.5h;
Stage #2: Phenyltrichlorosilane In hexane; toluene; 1,3,5-trimethyl-benzene at 90℃; for 24h;
A n/a
B 88%
Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

chlorobenzene
108-90-7

chlorobenzene

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With magnesium at 155℃; Inert atmosphere;A 67.2%
B 31.4%
triphenylsilyl fluoride
379-50-0

triphenylsilyl fluoride

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With AlCl3 In diethyl ether boiling of (C6H5)3SiF and AlCl3 in ether;;55%
Multi-step reaction with 2 steps
1: diethyl ether
2: not given
View Scheme
tetraphenylsilane
1048-08-4

tetraphenylsilane

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

PhSbCl4, SbCl3

PhSbCl4, SbCl3

Conditions
ConditionsYield
With antimonypentachloride In tetrachloromethaneA 30%
B n/a
diethyldichlorosilane
1719-53-5

diethyldichlorosilane

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

dichloro(ethyl)phenylsilane
1125-27-5, 18447-29-5

dichloro(ethyl)phenylsilane

C

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

Conditions
ConditionsYield
With aluminum (III) chloride at 120℃; for 3h; Overall yield = 64 %;A 7%
B 25%
C 28%
2-propynyl chloride
624-65-7

2-propynyl chloride

HSiPh3
789-25-3

HSiPh3

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

triphenylpropargylsilane
14657-23-9

triphenylpropargylsilane

C

((E)-3-Chloro-propenyl)-triphenyl-silane

((E)-3-Chloro-propenyl)-triphenyl-silane

Conditions
ConditionsYield
With dihydrogen hexachloroplatinate at 50℃; for 6h; Product distribution;A 24%
B 9%
C 7%
With dihydrogen hexachloroplatinate at 50℃; for 6h; Title compound not separated from byproducts;A 24%
B 9%
C 7%
HSiPh3
789-25-3

HSiPh3

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

triphenylpropargylsilane
14657-23-9

triphenylpropargylsilane

C

((E)-3-Chloro-propenyl)-triphenyl-silane

((E)-3-Chloro-propenyl)-triphenyl-silane

Conditions
ConditionsYield
With dihydrogen hexachloroplatinate; 2-propynyl chloride at 50℃; for 6h; Title compound not separated from byproducts;A 24%
B 9%
C 7%
ethyltrichlorosilane
115-21-9

ethyltrichlorosilane

phenylmagnesium bromide

phenylmagnesium bromide

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With diethyl ether
tetraphenylsilane
1048-08-4

tetraphenylsilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With tetrachlorosilane; copper(l) chloride at 300 - 360℃;
With phosphorus pentachloride at 180℃; und Erhitzen dann auf 240grad;
phenylchlorosilane
4206-75-1

phenylchlorosilane

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With aluminium trichloride
1-(triphenylsiloxy)-2-phenylethane
18758-56-0

1-(triphenylsiloxy)-2-phenylethane

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

Si(Oet-2-ph)4
18839-09-3

Si(Oet-2-ph)4

Conditions
ConditionsYield
With tetrachlorosilane
acetyl chloride
75-36-5

acetyl chloride

triphenylhydroxysilane
791-31-1

triphenylhydroxysilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

chlorobenzene
108-90-7

chlorobenzene

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

tetraphenylsilane
1048-08-4

tetraphenylsilane

Conditions
ConditionsYield
With tetrachlorosilane; sodium
phenylmagnesium bromide

phenylmagnesium bromide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

benzene
71-43-2

benzene

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With tetrachlorosilane at 980℃; in der Dampfphase;
hexaphenyldisilane
1450-23-3

hexaphenyldisilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
With n-Butyl chloride In cyclohexane at 23℃; Rate constant; Irradiation; other alkyl halides;
phenylmagnesium chloride

phenylmagnesium chloride

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
In tetrahydrofuran
1,1,1-trimethyl-2,2,2-triphenyldisilane
1450-18-6

1,1,1-trimethyl-2,2,2-triphenyldisilane

acetone
67-64-1

acetone

A

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

B

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

C

3,3-Dimethyl-1,1-diphenyl-9-trimethylsilanyl-2-oxa-1-sila-spiro[3.5]nona-5,7-diene

3,3-Dimethyl-1,1-diphenyl-9-trimethylsilanyl-2-oxa-1-sila-spiro[3.5]nona-5,7-diene

D

1-(Isopropoxy-diphenyl-silanyl)-2-trimethylsilanyl-benzene

1-(Isopropoxy-diphenyl-silanyl)-2-trimethylsilanyl-benzene

Conditions
ConditionsYield
With chloroform In Cyclohexane-d12 Product distribution; Irradiation; other disilane; var. solvents; also without CHCl3;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

triphenylhydroxysilane
791-31-1

triphenylhydroxysilane

A

Trimethylsilanol
1066-40-6

Trimethylsilanol

B

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Conditions
ConditionsYield
Equilibrium constant;
hydrogenchloride
7647-01-0

hydrogenchloride

diethyl ether
60-29-7

diethyl ether

triphenylhydroxysilane
791-31-1

triphenylhydroxysilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

acetyl chloride
75-36-5

acetyl chloride

triphenylhydroxysilane
791-31-1

triphenylhydroxysilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

tetraphenylsilane
1048-08-4

tetraphenylsilane

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

aluminium trichloride
7446-70-0

aluminium trichloride

phenylchlorosilane
4206-75-1

phenylchlorosilane

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

((i)Pr2N)2BP(H)Li * 1,2-dimethoxyethane

((i)Pr2N)2BP(H)Li * 1,2-dimethoxyethane

(((CH3)2CH)2N)2BP(H)Si(C6H5)3
235756-00-0

(((CH3)2CH)2N)2BP(H)Si(C6H5)3

Conditions
ConditionsYield
In hexane silylation; 1.) 0 deg C, 1 h, 2.) 23 deg C, 6 h;100%
In hexane byproducts: LiCl, DME; inert atmosphere; equimolar amts., stirring (0°C, 1 h; 23°C, 6 h); filtration off of LiCl, evapn. (vac.), crystn. on standing (23°C, several d); elem. anal.;100%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

1-triphenylsiloxy-ethane-2-thiol
205698-59-5

1-triphenylsiloxy-ethane-2-thiol

Conditions
ConditionsYield
With pyridine at 20℃;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;65%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

(2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-ol
350795-03-8

(2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-ol

(2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-triphenylsilyl ether
350795-04-9

(2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-triphenylsilyl ether

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 6h;100%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

2-hydroxy-4-iodo-1,3-dimethyl-cyclopent-3-enecarboxylic acid ethyl ester
637741-35-6

2-hydroxy-4-iodo-1,3-dimethyl-cyclopent-3-enecarboxylic acid ethyl ester

4-iodo-1,3-dimethyl-2-triphenylsilanyloxy-cyclopent-3-enecarboxylic acid ethyl ester
637741-36-7

4-iodo-1,3-dimethyl-2-triphenylsilanyloxy-cyclopent-3-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;100%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-bromophenyltriphenylsilane
18737-40-1

4-bromophenyltriphenylsilane

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -78℃;
Stage #2: Triphenylsilyl chloride In diethyl ether; hexane at -78 - 20℃; Further stages.;
100%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 2.33333h; Inert atmosphere;
Stage #2: Triphenylsilyl chloride In diethyl ether at -78 - 20℃; Inert atmosphere;
87.1%
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: Triphenylsilyl chloride at -78℃; for 2h;
85%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

C23H24OSi

C23H24OSi

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 22h;99%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

1,1,1-trimethyl-2,2,2-triphenyldisilane
1450-18-6

1,1,1-trimethyl-2,2,2-triphenyldisilane

Conditions
ConditionsYield
With C8K In tetrahydrofuran at 0℃; for 0.0833333h;98%
With lithium In tetrahydrofuran at 0℃; 1.) THF, room temp., 6 h;82%
With lithium In tetrahydrofuran for 20h; Ambient temperature;77%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester
246510-31-6

(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester

(2R,3S)-3-Phenylsulfanylcarbonyl-2-triphenylsilanyloxy-butyric acid ethyl ester
500103-02-6

(2R,3S)-3-Phenylsulfanylcarbonyl-2-triphenylsilanyloxy-butyric acid ethyl ester

Conditions
ConditionsYield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0℃;98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

Mesitol
527-60-6

Mesitol

1,3,5-trimethyl-2-(triphenylsilyloxy)benzene
234123-80-9

1,3,5-trimethyl-2-(triphenylsilyloxy)benzene

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃;98%
Stage #1: Mesitol With sodium In tetrahydrofuran Inert atmosphere; Schlenk technique;
Stage #2: Triphenylsilyl chloride In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Schlenk technique; Cooling with liquid nitrogen;
49%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

(2S,3S,6S)-6-(4-Methoxy-phenoxy)-2-methyl-3,6-dihydro-2H-pyran-3-ol
157430-14-3

(2S,3S,6S)-6-(4-Methoxy-phenoxy)-2-methyl-3,6-dihydro-2H-pyran-3-ol

C31H30O4Si

C31H30O4Si

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0℃;98%
C15(13)CH14O
1076068-52-4

C15(13)CH14O

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

C33(13)CH28OSi
1076068-56-8

C33(13)CH28OSi

Conditions
ConditionsYield
Stage #1: C15(13)CH14O With n-butyllithium In tetrahydrofuran at -20℃; for 2h;
Stage #2: Triphenylsilyl chloride In tetrahydrofuran at 20℃; for 3h; Further stages.;
98%
C15(13)CH14O

C15(13)CH14O

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

C33(13)CH28OSi

C33(13)CH28OSi

Conditions
ConditionsYield
Stage #1: C15(13)CH14O With n-butyllithium In tetrahydrofuran at -20℃; for 2h;
Stage #2: Triphenylsilyl chloride In tetrahydrofuran at 20℃; for 3h; Further stages.;
98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

1,1'-(3-methoxyprop-1-yne-3,3-diyl)dibenzene
13632-79-6

1,1'-(3-methoxyprop-1-yne-3,3-diyl)dibenzene

C34H28OSi
1076068-55-7

C34H28OSi

Conditions
ConditionsYield
Stage #1: 1,1'-(3-methoxyprop-1-yne-3,3-diyl)dibenzene With n-butyllithium In tetrahydrofuran at -20℃; for 2h;
Stage #2: Triphenylsilyl chloride In tetrahydrofuran at 20℃; for 3h; Further stages.;
98%
{niobium(I)(methyl isocyanide)(CO)(1,2-bis(dimethylphosphino)ethane)2Cl}
126296-34-2

{niobium(I)(methyl isocyanide)(CO)(1,2-bis(dimethylphosphino)ethane)2Cl}

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

C33H50NNbOP4Si

C33H50NNbOP4Si

Conditions
ConditionsYield
With Na/Hg In tetrahydrofuran addn. of excess 40% Na/Hg to the red soln. of Nb(CNMe)(CO)(dmpe)2Cl in THF, stirring 30 min, the resulting violet soln. decanted, addn. of Ph3SiCl, colour change to deep red over 30 min; vac. evapn., residue extd. into pentane, filtered, vac. evapn., orange red solid, elem. anal.;98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

buta-2,3-dien-2-yltriphenylsilane
850172-10-0

buta-2,3-dien-2-yltriphenylsilane

Conditions
ConditionsYield
Stage #1: 1-Bromo-2-butyne With indium In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: Triphenylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 3h;
98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

propargyl bromide
106-96-7

propargyl bromide

triphenyl(propa-1,2-dien-1-yl)silane
14583-75-6

triphenyl(propa-1,2-dien-1-yl)silane

Conditions
ConditionsYield
Stage #1: propargyl bromide With indium In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: Triphenylsilyl chloride at 20℃; for 3h;
98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

acetic anhydride
108-24-7

acetic anhydride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

C22H22O2SSi
1113062-55-7

C22H22O2SSi

Conditions
ConditionsYield
Stage #1: Triphenylsilyl chloride; 2-hydroxyethanethiol With triethylamine In dichloromethane at 20℃;
Stage #2: acetic anhydride In dichloromethane at 20℃; for 2h;
98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-trimethylsilyl-2-triphenylsilylacetylene
17146-53-1

1-trimethylsilyl-2-triphenylsilylacetylene

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether; hexane at -78 - 0℃; for 1h;
Stage #2: Triphenylsilyl chloride In diethyl ether; hexane at 0 - 20℃;
98%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

benzyl D-threonin p-toluenesulfonate
82679-59-2

benzyl D-threonin p-toluenesulfonate

benzyl D-threonin triphenylsilyl ether
143000-26-4

benzyl D-threonin triphenylsilyl ether

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;97.05%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

(R)-(+)-3,3'-dibromo-1,1'-bi-2-naphthol

(R)-(+)-3,3'-dibromo-1,1'-bi-2-naphthol

3,3'-Dibromo-2,2'-bis-triphenylsilanyloxy-[1,1']binaphthalenyl

3,3'-Dibromo-2,2'-bis-triphenylsilanyloxy-[1,1']binaphthalenyl

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 5h; Ambient temperature;97%

76-86-8Relevant articles and documents

Flash Photolysis Study for Halogen Abstraction of Ph3Sn* and Ph3Si* from Alkyl Halides

Ito, Osamu,Hoteiya, Kiyohiko,Watanabe, Akira,Matsuda, Minoru

, p. 962 - 965 (1991)

The reaction rate contants for halogen abstraction of Ph3Sn* and Ph3Si* have been determined by xenon-flash photolysis method.The absolute rate constants for the reactivity of Ph3Sn* with several alkyl halides have been compared with the relative ones; the agreement between the both methods was fairly good.For Ph3Sn*, the rate constant (in unit of mol-1 dm3 s-1) of n-BuCl (5.2*102) was smaller than that of n-BuBr (3.1*106) by a factor of ca. 1/104.With changing the alkyl halides, the rate constants for Ph3Si* and Ph3Sn* varied similarly, although the rate constants for Ph3Si* were larger than those for Ph3Sn* by factors of 50 - 100.The reactivity of alkyl halides increased with a decrease in the bond-dissociation energy of the R-X (X=Cl, Br).

Marr,Webster

, p. 93 (1964)

METHOD FOR PRODUCING ARYLSILANE COMPOUND CONTAINING HALOSILANE COMPOUND AS RAW MATERIAL

-

Paragraph 0080-0084, (2020/03/06)

PROBLEM TO BE SOLVED: To provide a method for producing an arylsilane compound with low production cost. SOLUTION: A method for producing an arylsilane compound includes a reaction step for the cross-coupling reaction of a halosilane compound represented by general formula (A-1), (A-2), or (A-3) and an arylboronic acid pinacol ester in the presence of a nickel catalyst, a Lewis acid catalyst, and an organic base (R independently represent an aromatic hydrocarbon group, a heteroaromatic ring group, or a C1-20 hydrocarbon group; X independently represent a halogeno group or a trifluoromethanesulfonyloxy group). SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Kinetic and Theoretical Investigation of Iron(III)-Catalyzed Silane Chlorination

Savela, Risto,Grnman, Henrik,Sundelin, Heidi,Norrby, Per-Ola,Yu. Murzin, Dmitry,Leino, Reko

, p. 584 - 592 (2016/02/23)

A highly versatile, robust, and efficient methodology for chlorination of silanes, methoxysilanes and silanols using low loadings of FeCl3 or Fe(acac)3 as the catalyst in the presence of 1-1.5?equivalents of acetyl chloride as the chlorine source was recently developed. The aim of the present paper is to evaluate and derive the reaction mechanisms involved in this reaction by calculating substrates, intermediates, products, and selected transition states, as well as by employing mathematical modeling of the reaction kinetics. The results obtained required reconsideration of the originally proposed overall reaction mechanism. Based on the kinetic and molecular modeling, a new revised reaction mechanism was developed giving a very good correspondence between the experimental data and calculations.

Iron-catalyzed chlorination of silanes

Savela, Risto,Zawartka, Wojciech,Leino, Reko

experimental part, p. 3199 - 3206 (2012/06/04)

A simple and highly efficient iron-catalyzed method for the chlorination of silanes has been developed. By use of 0.5-2% of the Fe(III)-based catalyst FeCl3 or Fe(acac)3 in the presence of 1-1.5 equiv of acetyl chloride as the chlorine donor, a large number of silanes, alkoxysilanes, and silanols were converted to the corresponding chlorosilanes in 50-93% yields. In contrast to earlier reported methods often suffering from expensive catalysts or use of stoichiometric metal salts, hazardous reagents, and reaction conditions, the presently described methodology allows benign reaction conditions and simple workup while using only catalytic amounts of a readily available and economically viable iron catalyst.

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