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80-10-4

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80-10-4 Usage

Chemical Properties

Diphenyldichlorosilane is a colorless liquid with a pungent odor. It will burn though it may require some effort to ignite. It is decomposed by water to hydrochloric acid with evolution of heat. It is corrosive to metals and tissue.

Uses

Dichlorodiphenylsilane is a silane based surface modifier, and a precursor which can be used in the synthesis of silica based materials. It is used to modify the surface by providing toughness, durability and resistance to shock. It can be used in the synthesis of a host material for the fabrication of blue phosphorescent organic light emitting diodes (OLEDs).

Reactivity Profile

Chlorosilanes, such as Dichlorodiphenylsilane, are compounds in which silicon is bonded to from one to four chlorine atoms with other bonds to hydrogen and/or alkyl groups. Chlorosilanes react with water, moist air, or steam to produce heat and toxic, corrosive fumes of hydrogen chloride. They may also produce flammable gaseous H2. They can serve as chlorination agents. Chlorosilanes react vigorously with both organic and inorganic acids and with bases to generate toxic or flammable gases.

Flammability and Explosibility

Notclassified

Safety Profile

A poison irritant to skin, eyes, and mucous membranes. See also CHLOROSILANES. Can react vigorously with oxidizing materials. When heated to decomposition or on contact with acid or acid fumes it emits toxic fumes of Cl-.

Check Digit Verification of cas no

The CAS Registry Mumber 80-10-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 80-10:
(4*8)+(3*0)+(2*1)+(1*0)=34
34 % 10 = 4
So 80-10-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H10.Cl2H2Si/c1-3-7-11(8-4-1)12-9-5-2-6-10-12;1-3-2/h1-10H;3H2

80-10-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D0362)  Dichlorodiphenylsilane  >98.0%(GC)

  • 80-10-4

  • 25g

  • 190.00CNY

  • Detail
  • TCI America

  • (D0362)  Dichlorodiphenylsilane  >98.0%(GC)

  • 80-10-4

  • 100g

  • 365.00CNY

  • Detail
  • TCI America

  • (D0362)  Dichlorodiphenylsilane  >98.0%(GC)

  • 80-10-4

  • 500g

  • 995.00CNY

  • Detail
  • Alfa Aesar

  • (A12051)  Diphenyldichlorosilane, 97%   

  • 80-10-4

  • 100g

  • 228.0CNY

  • Detail
  • Alfa Aesar

  • (A12051)  Diphenyldichlorosilane, 97%   

  • 80-10-4

  • 500g

  • 981.0CNY

  • Detail
  • Aldrich

  • (D61504)  Dichlorodiphenylsilane  97%

  • 80-10-4

  • D61504-5G

  • 375.57CNY

  • Detail
  • Aldrich

  • (D61504)  Dichlorodiphenylsilane  97%

  • 80-10-4

  • D61504-100G

  • 775.71CNY

  • Detail
  • Aldrich

  • (440124)  Dichlorodiphenylsilane  

  • 80-10-4

  • 440124-100ML

  • 455.13CNY

  • Detail
  • Aldrich

  • (440124)  Dichlorodiphenylsilane  

  • 80-10-4

  • 440124-500ML

  • 1,670.76CNY

  • Detail
  • Sigma-Aldrich

  • (42930)  Dichlorodiphenylsilane  purum, ≥98.0% (GC)

  • 80-10-4

  • 42930-1L

  • 4,185.09CNY

  • Detail

80-10-4SDS

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 Dichlorodiphenylsilane

1.2 Other means of identification

Product number -
Other names dichloro(diphenyl)silane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:80-10-4 SDS

80-10-4Synthetic route

diphenylsilane
775-12-2

diphenylsilane

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With tellurium tetrachloride In benzene for 3h; Heating;95%
With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 4h; Inert atmosphere;94.1%
With dichloromethane; eosin y at 50℃; Temperature; Reagent/catalyst; Flow reactor; Inert atmosphere; Irradiation;99 %Spectr.
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%
bromobenzene
108-86-1

bromobenzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
Stage #1: bromobenzene With n-butyllithium In diethyl ether; hexane
Stage #2: With tetrachlorosilane In diethyl ether; hexane at 0 - 5℃;
Stage #1: bromobenzene With n-butyllithium In diethyl ether at -78℃;
Stage #2: With tetrachlorosilane In diethyl ether at 0 - 20℃;
Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

chlorobenzene
108-90-7

chlorobenzene

A

phenylchlorosilane
4206-75-1

phenylchlorosilane

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
Stage #1: Phenyltrichlorosilane With hydrogenchloride In water at 350 - 400℃; under 1500.15 Torr; for 3h;
Stage #2: chlorobenzene at 350 - 480℃; under 1500.15 Torr; for 10h; Reagent/catalyst; Temperature;
Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

chlorobenzene
108-90-7

chlorobenzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With magnesium at 185℃; for 17.5h; Inert atmosphere;68%
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%
diphenylsilyl chloride
1631-83-0

diphenylsilyl chloride

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With hexachloroethane; palladium dichloride at 20℃; for 1h;89%
With hydrogenchloride; ether adduct of tris(pentafluorophenyl)boron In toluene at 20℃; for 150h; Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen;61 %Spectr.
With dichloromethane; eosin y at 20℃; for 4h; Reagent/catalyst; Inert atmosphere; Irradiation; Green chemistry;99 %Spectr.
chlorobenzene
108-90-7

chlorobenzene

A

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With silicon-copper at 400℃;
With silver; silicon at 400℃;
With iron; silicon at 550℃;
With silicon-copper at 420℃;
chlorobenzene
108-90-7

chlorobenzene

silicon
7440-21-3

silicon

A

biphenyl
92-52-4

biphenyl

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
tin at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
tin; copper; zinc at 480℃; Product distribution / selectivity;
tin; copper at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
chlorobenzene
108-90-7

chlorobenzene

A

biphenyl
92-52-4

biphenyl

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With silicon; tin(ll) chloride at 450 - 500℃; for 2h; Product distribution / selectivity;
With silicon; tin; copper; zinc at 450℃; Product distribution / selectivity;
With silicon; tin; zinc at 450℃; Product distribution / selectivity;
With silicon; tin at 450℃; Product distribution / selectivity;
phenylmagnesium bromide

phenylmagnesium bromide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With diethyl ether; hexachlorodisilane
With tetrachlorosilane; diethyl ether; benzene
With tetrachlorosilane; diethyl ether
chlorobenzene
108-90-7

chlorobenzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With silicon; tin(ll) chloride at 450 - 500℃; for 3h; Product distribution / selectivity;
chlorobenzene
108-90-7

chlorobenzene

A

biphenyl
92-52-4

biphenyl

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With silicon; tin at 450℃; for 1h; Product distribution / selectivity;
With silicon; copper at 450℃; for 1h; Product distribution / selectivity;
chlorobenzene
108-90-7

chlorobenzene

silicon
7440-21-3

silicon

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
tin at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
chlorobenzene
108-90-7

chlorobenzene

silicon
7440-21-3

silicon

A

biphenyl
92-52-4

biphenyl

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
tin at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
tin at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
diethoxydiphenylsilane
2553-19-7

diethoxydiphenylsilane

benzoyl chloride
98-88-4

benzoyl chloride

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With pyridine
In neat (no solvent) boiling of (C6H5)Si(OC2H5)2 and C6H5COCl in presence of some pyridine for a longer period of time;;
In neat (no solvent) boiling of (C6H5)Si(OC2H5)2 and C6H5COCl in presence of some pyridine for a longer period of time;;
dichloro(o-chlorophenyl)phenylsilane
36964-86-0

dichloro(o-chlorophenyl)phenylsilane

A

9,9-dichloro-9-silafluorene
18030-58-5

9,9-dichloro-9-silafluorene

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

chlorobenzene
108-90-7

chlorobenzene

D

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With hexachlorodisilane at 500℃; gas phase; Further byproducts given;A 95%
B 0.3 g
C 0.8 g
D 0.2 g
chlorobenzene
108-90-7

chlorobenzene

silicon
7440-21-3

silicon

A

biphenyl
92-52-4

biphenyl

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
tin at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
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
Dichlorosilane
4109-96-0

Dichlorosilane

chlorobenzene
108-90-7

chlorobenzene

A

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
1,1'-(1,2-ethanediyl)bisbenzene at 650℃; for 0.5h; Product distribution / selectivity;A 10.7%
B 5.11%
C 8.87%
chlorobenzene
108-90-7

chlorobenzene

silicon
7440-21-3

silicon

A

biphenyl
92-52-4

biphenyl

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
tin at 480℃; Product distribution / selectivity;
tin; copper; zinc at 480℃; Product distribution / selectivity;
tin at 480℃; Product distribution / selectivity;
dichloro(o-chlorophenyl)phenylsilane
36964-86-0

dichloro(o-chlorophenyl)phenylsilane

A

1,9,9-trichloro-9-silafluorene
104972-38-5

1,9,9-trichloro-9-silafluorene

B

9,9-dichloro-9-silafluorene
18030-58-5

9,9-dichloro-9-silafluorene

C

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

D

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With chloroform at 620℃; gas phase;A 44%
B 4.5%
C 1.5 g
D 4.5 g
hexachlorodisilane
13465-77-5

hexachlorodisilane

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With phenylmagnesium bromide In not given
With C6H5MgBr In not given
dichlorophenylsilane
1631-84-1

dichlorophenylsilane

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With boron trichloride at 185℃;
With aluminium trichloride at 185℃;
dichloro(o-chlorophenyl)phenylsilane
36964-86-0

dichloro(o-chlorophenyl)phenylsilane

A

9,9-dichloro-9-silafluorene
18030-58-5

9,9-dichloro-9-silafluorene

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

D

toluene
108-88-3

toluene

Conditions
ConditionsYield
With 1,1-Dichloro-2,5-dihydro-1H-silole at 600℃; gas phase; Further byproducts given. Title compound not separated from byproducts;A 30%
B 0.5 g
C 0.8 g
D n/a
dichloromethylphenylsilane
149-74-6

dichloromethylphenylsilane

A

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With aluminum (III) chloride at 120℃; for 3h;A 6%
B 6%
tetraphenylsilane
1048-08-4

tetraphenylsilane

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With phosphorus pentachloride at 180 - 240℃;
benzene
71-43-2

benzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With tetrachlorosilane at 840℃; in der Dampfphase;
tetrachlorosilane
10026-04-7, 53609-55-5

tetrachlorosilane

A

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

B

Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

C

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With phenylmagnesium bromide In diethyl ether SiCl4 (1 mol) and C6H5MgBr (2.25 mol) in boiling ether;;
With C6H5MgBr In diethyl ether SiCl4 (1 mol) and C6H5MgBr (2.25 mol) in boiling ether;;
Dichlorosilane
4109-96-0

Dichlorosilane

A

dichlorophenylsilane
1631-84-1

dichlorophenylsilane

B

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Conditions
ConditionsYield
With benzene In neat (no solvent) H2SiCl2 and C6H6 with a Zn-halide as catalyst at 400°C;;
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

1,3-diallyl-4-(trimethylsilyloxy)-2,6-dioxo-1,3,5-triazine
63226-47-1

1,3-diallyl-4-(trimethylsilyloxy)-2,6-dioxo-1,3,5-triazine

bis(diallylisocyanurato)diphenylsilane

bis(diallylisocyanurato)diphenylsilane

Conditions
ConditionsYield
at 120 - 160℃;99.6%
DDBA

DDBA

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C100H88O12P4Si

C100H88O12P4Si

Conditions
ConditionsYield
In tetrahydrofuran at 40℃; for 6h;99.5%
DDBA

DDBA

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C156H136O18P6Si2

C156H136O18P6Si2

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 10h;99.3%
(S)-4-trimethylsilyl-3-butyn-2-ol
6999-19-5, 103253-60-7, 121522-26-7, 121522-27-8

(S)-4-trimethylsilyl-3-butyn-2-ol

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C26H36O2Si3
462660-34-0

C26H36O2Si3

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 0 - 23℃; for 4h;99%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

allylsamarium bromide
346713-20-0

allylsamarium bromide

diallyldiphenylsilane
10519-88-7

diallyldiphenylsilane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;99%
allyl bromide
106-95-6

allyl bromide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

diallyldiphenylsilane
10519-88-7

diallyldiphenylsilane

Conditions
ConditionsYield
Stage #1: allyl bromide With indium In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: diphenylsilyl dichloride In N,N-dimethyl-formamide at 20℃; for 3h;
99%
With zinc In tetrahydrofuran for 0.166667h; Inert atmosphere; Sonication;88%
ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Dimethyldiphenylsilane
778-24-5

Dimethyldiphenylsilane

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;99%
lithium 1,2,3,4-tetramethylcyclopentadienide

lithium 1,2,3,4-tetramethylcyclopentadienide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

diphenylsilyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl) chloride

diphenylsilyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl) chloride

Conditions
ConditionsYield
In tetrahydrofuran at -25 - 20℃;99%
tetrakis(trimethylsilyl)silane
4098-98-0

tetrakis(trimethylsilyl)silane

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

1-chloro-1,1-diphenyl-2,2-bis(trimethylsilyl)trimethyltrisilane
101690-46-4

1-chloro-1,1-diphenyl-2,2-bis(trimethylsilyl)trimethyltrisilane

Conditions
ConditionsYield
Stage #1: tetrakis(trimethylsilyl)silane With potassium tert-butylate In 1,2-dimethoxyethane for 6h;
Stage #2: diphenylsilyl dichloride In 1,2-dimethoxyethane; toluene for 14h;
99%
phenylborondichloride
873-51-8

phenylborondichloride

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

{((C6H5)2Si)4(B(C6H5))(CH2)5}

{((C6H5)2Si)4(B(C6H5))(CH2)5}

Conditions
ConditionsYield
With sodium; 1,2-dibromomethane In xylene Ar; to suspension of Na were added at 138°C during 1.5 h silane and borane (4:1) and CH2Br2; 30 min reflux; filtration; evapn. of solvent and drying at 100°C for 20 h (vacuo); elem. anal.;98.8%
silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Diphenylsilicium-bis(trifluormethansulfonat)
27607-80-3

Diphenylsilicium-bis(trifluormethansulfonat)

Conditions
ConditionsYield
In dichloromethane at -25 - 20℃;98%
96 h,25°C;80%
1,2-dimethyl-4,5-di(mercaptomethyl)benzene
10230-61-2

1,2-dimethyl-4,5-di(mercaptomethyl)benzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

9,10-Dimethyl-2,2-diphenyl-5,6-benzo-1,3,2-dithiasilepine
135419-30-6

9,10-Dimethyl-2,2-diphenyl-5,6-benzo-1,3,2-dithiasilepine

Conditions
ConditionsYield
With triethylamine In benzene for 5h; Heating;98%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

diphenyl-divinyl-silane
17937-68-7

diphenyl-divinyl-silane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 12h; Grignard reaction;98%
In tetrahydrofuran; pentane for 12h; Heating;80%
sodium tri-tert-butylsilanide
103349-41-3

sodium tri-tert-butylsilanide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

Chlordiphenylsupersilylsilan

Chlordiphenylsupersilylsilan

Conditions
ConditionsYield
In tetrahydrofuran Substitution; supersilanidation;98%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

allylsamarium bromide
346713-20-0

allylsamarium bromide

allyl(chloro)diphenylsilane
41422-93-9

allyl(chloro)diphenylsilane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;98%
propargyl bromide
106-96-7

propargyl bromide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

diallenyldiphenylsilane

diallenyldiphenylsilane

Conditions
ConditionsYield
Stage #1: propargyl bromide With indium In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: diphenylsilyl dichloride In N,N-dimethyl-formamide at 20℃; for 3h;
98%
phenylacetylene
536-74-3

phenylacetylene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

1,1-diphenylbis(phenylethynyl)silane
18784-61-7

1,1-diphenylbis(phenylethynyl)silane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -70℃;97%
With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; lithium iodide at 100℃; for 72h; Schlenk technique; Inert atmosphere;90%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;90%
ethynylmagnesium chloride
65032-27-1

ethynylmagnesium chloride

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

diethynyldiphenylsilane
1675-57-6

diethynyldiphenylsilane

Conditions
ConditionsYield
In tetrahydrofuran at 30 - 40℃; for 3h;97%
Stage #1: ethynylmagnesium chloride; diphenylsilyl dichloride In tetrahydrofuran for 1h; Inert atmosphere;
Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;
70%
In tetrahydrofuran
cyclohexenone
930-68-7

cyclohexenone

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

3-phenylcyclohexanone
20795-53-3

3-phenylcyclohexanone

Conditions
ConditionsYield
With air; sodium fluoride; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate at 100℃; for 12h;97%
1,2-bis(1H-indol-2-yl)benzene

1,2-bis(1H-indol-2-yl)benzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

1,2-bis(indol-2-yl)benzene N1,N2-diphenylsilyl

1,2-bis(indol-2-yl)benzene N1,N2-diphenylsilyl

Conditions
ConditionsYield
Stage #1: 1,2-bis(1H-indol-2-yl)benzene With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.25h;
Stage #2: diphenylsilyl dichloride In tetrahydrofuran; toluene at 0 - 20℃; for 12h;
97%
ethanol
64-17-5

ethanol

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

diethoxydiphenylsilane
2553-19-7

diethoxydiphenylsilane

Conditions
ConditionsYield
With polyaniline at 40 - 50℃; for 8h;96%
In diethyl ether at 40℃; for 3h; Inert atmosphere;76.92%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

difluorodiphenylsilane
312-40-3

difluorodiphenylsilane

Conditions
ConditionsYield
With sodium tetrafluoroborate In various solvent(s) for 0.75h; Heating;96%
With hydrogen fluoride In ethanol at 20℃;90%
With ammonium hexafluorosilicate In 1,2-dimethoxyethane at 0℃; for 0.333333h; Product distribution; var. react.: Na2SiF6, var. solv., temp and time;82%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C15H13N2S2(1-)*Na(1+)

C15H13N2S2(1-)*Na(1+)

C42H36N4S4Si

C42H36N4S4Si

Conditions
ConditionsYield
In benzene for 12h; Heating;96%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

N,N'-Bis(trimethylsilyl)-N,N',N'',N'''-tetrakis(4-methylphenyl)oxalamidin

N,N'-Bis(trimethylsilyl)-N,N',N'',N'''-tetrakis(4-methylphenyl)oxalamidin

C42H38N4Si

C42H38N4Si

Conditions
ConditionsYield
With ammonium fluoride; 18-crown-6 ether In hexane; toluene for 10h; Heating;96%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

disilver 1,2-ethanedisulfonate

disilver 1,2-ethanedisulfonate

3,3-Diphenyl-2,4-dioxa-1,5-dithia-1,1,5,5-tetraoxid-3-silacycloheptane

3,3-Diphenyl-2,4-dioxa-1,5-dithia-1,1,5,5-tetraoxid-3-silacycloheptane

Conditions
ConditionsYield
In chloroform for 6h; Heating;96%
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

1,4-diphenylbut-2-ene-1,4-dione
959-28-4

1,4-diphenylbut-2-ene-1,4-dione

1,2,4-triphenylbutane-1,4-dione
4441-01-4

1,2,4-triphenylbutane-1,4-dione

Conditions
ConditionsYield
With air; sodium fluoride; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate at 100℃; for 12h;96%
2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

C37H46N2
587023-11-8

C37H46N2

Conditions
ConditionsYield
Stage #1: 2,6-diisopropylbenzenamine With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
Stage #2: diphenylsilyl dichloride In diethyl ether; hexane at -78℃; Inert atmosphere;
96%
Stage #1: 2,6-diisopropylbenzenamine With n-butyllithium In diethyl ether; hexane; Petroleum ether at -78 - 20℃;
Stage #2: diphenylsilyl dichloride In Petroleum ether at -78℃; for 8h;
66%
With n-butyllithium In diethyl ether; hexane; Petroleum ether at -78 - 20℃; for 8h;
diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

bis((trimethylsilyl)ethynyl)diphenylsilane
25284-31-5

bis((trimethylsilyl)ethynyl)diphenylsilane

Conditions
ConditionsYield
With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; lithium iodide at 100℃; for 72h; Schlenk technique; Inert atmosphere;96%
Stage #1: trimethylsilylacetylene With n-butyllithium In diethyl ether; hexane at -78 - 0℃; for 1h;
Stage #2: diphenylsilyl dichloride In diethyl ether; hexane at 0 - 20℃;
87%
With n-butyllithium In diethyl ether; hexane at -78 - 20℃;72%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

bis(4-bromophenyl)(diphenyl)silane
18733-91-0

bis(4-bromophenyl)(diphenyl)silane

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: diphenylsilyl dichloride In tetrahydrofuran at -78 - 20℃; for 14h; Inert atmosphere;
96%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at 0℃; for 3h; Inert atmosphere;
Stage #2: diphenylsilyl dichloride In diethyl ether at 20℃; for 48h; Inert atmosphere;
85%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 2.5h; Inert atmosphere;
Stage #2: diphenylsilyl dichloride In diethyl ether at -78 - 20℃; Inert atmosphere;
82.9%
allyl bromide
106-95-6

allyl bromide

diphenylsilyl dichloride
80-10-4

diphenylsilyl dichloride

A

diallyldiphenylsilane
10519-88-7

diallyldiphenylsilane

B

allyl(chloro)diphenylsilane
41422-93-9

allyl(chloro)diphenylsilane

Conditions
ConditionsYield
Stage #1: allyl bromide With indium In 1,3-dimethylimidazolidine at 20℃; for 1h;
Stage #2: diphenylsilyl dichloride In 1,3-dimethylimidazolidine at 70℃; for 3h;
A 3%
B 96%

80-10-4Relevant articles and documents

-

Rochow,Gilliam

, p. 1772 (1945)

-

Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

Fan, Xuanzi,Xiao, Pin,Jiao, Zeqing,Yang, Tingting,Dai, Xiaojuan,Xu, Wengang,Tan, Jin Da,Cui, Ganglong,Su, Hongmei,Fang, Weihai,Wu, Jie

, p. 12580 - 12584 (2019/08/16)

Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si?H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.

Electrochemical properties of arylsilanes

Biedermann, Judith,Wilkening, H. Martin R.,Uhlig, Frank,Hanzu, Ilie

, p. 13 - 18 (2019/03/27)

In the past, the electrochemical properties of organosilicon compounds were investigated for both fundamental reasons and synthesis purposes. Little is, however, known about the electrochemical behaviour of hydrogen-bearing arylsilanes. Here, we throw light on the electrochemical properties of 11 arylsilanes compounds, 2 of them synthesized for the first time. The oxidation potentials are found to depend on both the nature and number of the aryl groups. Based on these findings it was possible to establish some variation trends that match the expected structure–property correlations. Furthermore, we present first insights into the electrochemical reaction kinetics behind and identify several soluble electrochemical oxidation products.

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