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4342-61-4

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4342-61-4 Usage

Description

1,2-DICHLOROTETRAMETHYLDISILANE is a kind of widely used organic silicon intermediates and usually be used as organic silicon blocking agent in the synthesis,such as,Si-Si Compounds; Dichlorosilanes (for Polysilanes); Electroluminescence; Functional Materials; Monochlorosilanes; Reagent for High-Performance Polymer Research; Si (Classes of Silicon Compounds); Si-Cl Compounds; Silicon Compounds (for Synthesis); Synthetic Organic Chemistry; Precursors by Metal; Vapor Deposition Precursors.

Uses

1,2-DICHLOROTETRAMETHYLDISILANE is used as an intermediate for preparing other organical compounds. It is also used in aqueous polymer preparation as well as a laboratory reagent. 1,2-Dihydroxy-tetramethyldisilane has been synthesized by hydrolysis of 1,2-dichloro-tetramethyldisilane and characterized by IR, NMR, MS and X-ray structure analysis.

Synthesis

Tetramethyldisilane (XIV, 0.3 mmol), excess MeSiC (IV, 1.7 mmol), diglyme (0.35 ml) and n-Bu4PCI (0.02 mmol) as catalyst were placed in an NMR tube that was cooled to -196 °C (liquid nitrogen). After evacuation in vacuo the NMR tube was sealed, warmed to r.t. and the reaction course was monitored by NMR spectroscopy. Me2SiHCI III was not detected at r.t. but the disilane was chlorinated to give disilane XV (12%). Reduction of MeSiC (H-transfer from disilane XIV) yielded V in small amounts (1.2%) while target product VI was formed in nearly 40% yield (80 °C/+4 h). At 120 °C (additional 19 h) disilane XV was reduced by about a half (1 1.9% → 6.7%) to form dimethyldichlorosilane II in 13.8% yield. The catalyst remained unreacted as shown by31P-NMR spectroscopy.

Check Digit Verification of cas no

The CAS Registry Mumber 4342-61-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,4 and 2 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 4342-61:
(6*4)+(5*3)+(4*4)+(3*2)+(2*6)+(1*1)=74
74 % 10 = 4
So 4342-61-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H12Cl2Si2/c1-7(2,5)8(3,4)6/h1-4H3

4342-61-4 Well-known Company Product Price

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

  • (D2144)  1,2-Dichlorotetramethyldisilane  >95.0%(GC)

  • 4342-61-4

  • 5g

  • 380.00CNY

  • Detail
  • TCI America

  • (D2144)  1,2-Dichlorotetramethyldisilane  >95.0%(GC)

  • 4342-61-4

  • 25g

  • 980.00CNY

  • Detail
  • Aldrich

  • (415456)  1,2-Dichlorotetramethyldisilane  95%

  • 4342-61-4

  • 415456-5ML

  • 762.84CNY

  • Detail

4342-61-4Synthetic route

1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With chloro-trimethyl-silane; aluminium trichloride88%
With aluminium trichloride; acetyl chloride at 0℃; for 20h;78%
With aluminium trichloride; acetyl chloride In dichloromethane at 40℃; for 12h;76%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

pentamethylchlorodisilane
1560-28-7

pentamethylchlorodisilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With aluminum (III) chloride at 70℃;74%
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

D

1,5-dichlorodecamethylpentasilane
5586-42-5

1,5-dichlorodecamethylpentasilane

Conditions
ConditionsYield
With tin(IV) chloride at 175℃; for 1h; Product distribution; Further Variations:; Reagents; Temperatures; reaction times;A 16.5%
B 10%
C 12.7%
D 49.5%
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

D

1,6-dichlorododecamethylhexasilane
812-54-4

1,6-dichlorododecamethylhexasilane

Conditions
ConditionsYield
With thionyl chloride In 1,1,2,2-tetrachloroethylene at 146℃; for 4h; Product distribution; other permethylated cyclosilane; var. solvents, time, temp.;A 24%
B 20%
C 18%
D 28%
With tin(IV) chloride at 175℃; for 0.5h; Further byproducts given;A 11.3%
B 7.5%
C 9.6%
D 46.1 % Chromat.
With mercury dichloride at 210℃; for 2h;A 40.8 % Chromat.
B 30.0 % Chromat.
C 21.9 % Chromat.
D 2.1 % Chromat.
polydimethylsilane

polydimethylsilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

D

1,5-dichlorodecamethylpentasilane
5586-42-5

1,5-dichlorodecamethylpentasilane

Conditions
ConditionsYield
With tin(IV) chloride at 180℃; for 3h; Product distribution; Further Variations:; Reagents; Temperatures; reaction times;A 27.9%
B 10.1%
C 25.5%
D 18.3%
1,2-diethoxy-1,1,2,2-tetramethyldisilane
18419-84-6

1,2-diethoxy-1,1,2,2-tetramethyldisilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With pyridine
1,2-diphenyltetramethyldisilane
1145-98-8

1,2-diphenyltetramethyldisilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With hydrogenchloride Ambient temperature;
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With chlorine
1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

A

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1,1,2-trichloro-1,2,2-trimethyldisilane
13528-88-6

1,1,2-trichloro-1,2,2-trimethyldisilane

D

1,1,2,2-tetrachloro-1,2-dimethyldisilane
4518-98-3

1,1,2,2-tetrachloro-1,2-dimethyldisilane

E

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

Conditions
ConditionsYield
With hexachlorodisilane; aluminium trichloride In benzene-d6 at 200℃; for 120h; Product distribution; var. temp.;A 15 % Spectr.
B 6 % Spectr.
C 15 % Spectr.
D 3 % Spectr.
E 60 % Spectr.
1,1,2-trichloro-1,2,2-trimethyldisilane
13528-88-6

1,1,2-trichloro-1,2,2-trimethyldisilane

benzyl chloride
100-44-7

benzyl chloride

A

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

B

benzyl(methyl)dichlorosilane
18236-82-3

benzyl(methyl)dichlorosilane

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In 1,3,5-trimethyl-benzene at 80℃; for 2h; Heating;A 2 % Chromat.
B 98 % Chromat.
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

D

1,5-dichlorodecamethylpentasilane
5586-42-5

1,5-dichlorodecamethylpentasilane

E

1,2-Dichloro-1,2,3,3,4,4,5,5,6,6-decamethyl-hexasilinane

1,2-Dichloro-1,2,3,3,4,4,5,5,6,6-decamethyl-hexasilinane

Conditions
ConditionsYield
With chlorine In tetrachloromethane also chlorination of 1,4-Cl2Si4Me8;
dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran also methylphenyldichlorosilane;
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

chloroundecamethylcyclohexasilane
23118-87-8

chloroundecamethylcyclohexasilane

D

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

E

1,6-dichlorododecamethylhexasilane
812-54-4

1,6-dichlorododecamethylhexasilane

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane for 30h; Product distribution; further reagent: TiCl4;
tetrachloromethane
56-23-5

tetrachloromethane

dimethylsilylene
6376-86-9

dimethylsilylene

A

chloroform
67-66-3

chloroform

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

(trichloromethyl)dimethylchlorosilane
18171-30-7

(trichloromethyl)dimethylchlorosilane

D

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

Conditions
ConditionsYield
Addition; Insertion;
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

chloroundecamethylcyclohexasilane
23118-87-8

chloroundecamethylcyclohexasilane

D

1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

Conditions
ConditionsYield
With antimonypentachloride at 25℃; for 0.002h; Product distribution; Further Variations:; Temperatures; Reagents;A 11.4 % Chromat.
B 43.4 % Chromat.
C 4.5 % Chromat.
D 10.8 % Chromat.
With tin(IV) chloride at 175℃; for 1h; Further byproducts given;A 34.7 % Chromat.
B 29.9 % Chromat.
C 2 % Chromat.
D 25.8 % Chromat.
dodecamethylcyclohexasilane
4098-30-0

dodecamethylcyclohexasilane

A

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane
812-36-2

1,3-dichloro-1,1,2,2,3,3-hexamethyltrisilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

chloroundecamethylcyclohexasilane
23118-87-8

chloroundecamethylcyclohexasilane

D

1,6-dichlorododecamethylhexasilane
812-54-4

1,6-dichlorododecamethylhexasilane

Conditions
ConditionsYield
With molybdenum(V) chloride at 185℃; for 3h; Further byproducts given;A 6.3 % Chromat.
B 10.9 % Chromat.
C 14.0 % Chromat.
D 17.8 % Chromat.
1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

A

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

B

dimethylsilane
1111-74-6

dimethylsilane

C

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

D

1-chloro-2-hydro-1,1,2,2-tetramethyldisilane
4455-83-8

1-chloro-2-hydro-1,1,2,2-tetramethyldisilane

Conditions
ConditionsYield
With tetra-n-butylphosphonium chloride In diethylene glycol dimethyl ether at -196 - 120℃; Sealed tube;A 50 %Spectr.
B 7 %Spectr.
C 9 %Spectr.
D 7 %Spectr.
With tetra-n-butylphosphonium chloride In diethylene glycol dimethyl ether at -196 - 120℃; Sealed tube;A 45 %Spectr.
B 11.3 %Spectr.
C 11.4 %Spectr.
D 12.3 %Spectr.
Methyltrichlorosilane
75-79-6

Methyltrichlorosilane

1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

A

Dichloromethylsilane
75-54-7

Dichloromethylsilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

Conditions
ConditionsYield
With tetra-n-butylphosphonium chloride In diethylene glycol dimethyl ether at -196 - 80℃; Temperature; Sealed tube;A 37.9 %Spectr.
B 6.7 %Spectr.
C 13.8 %Spectr.
Methyltrichlorosilane
75-79-6

Methyltrichlorosilane

1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

A

Dichloromethylsilane
75-54-7

Dichloromethylsilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With tetra-n-butylphosphonium chloride In diethylene glycol dimethyl ether at -196 - 80℃; Temperature; Sealed tube;A 38.7 %Spectr.
B 11.9 %Spectr.
1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

A

Dichloromethylsilane
75-54-7

Dichloromethylsilane

B

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

C

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With hydrogenchloride In dibutyl ether; water at 80℃; for 24h; Temperature; Solvent;A 10.1 %Spectr.
B 84.7 %Spectr.
C 5.2 %Spectr.
1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

A

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With hydrogenchloride In dibutyl ether; water at 100℃; for 24h;A 94.1 %Spectr.
B 5.9 %Spectr.
With hydrogenchloride In dibutyl ether; benzene-d6 at 100℃; for 24h; Sealed tube;
1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Conditions
ConditionsYield
With hydrogenchloride; tetra-n-butylphosphonium chloride In dibutyl ether; benzene-d6 at 80℃; for 18h; Reagent/catalyst; Sealed tube;
1,1,2,2-tetramethyldisilane
814-98-2

1,1,2,2-tetramethyldisilane

A

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

B

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C

1-chloro-2-hydro-1,1,2,2-tetramethyldisilane
4455-83-8

1-chloro-2-hydro-1,1,2,2-tetramethyldisilane

Conditions
ConditionsYield
With hydrogenchloride In dibutyl ether; benzene-d6 at 40℃; for 144h; Temperature; Time; Sealed tube;
1,1,2-trichloro-1,2,2-trimethyldisilane
13528-88-6

1,1,2-trichloro-1,2,2-trimethyldisilane

1,1,2,2-tetrachloro-1,2-dimethyldisilane
4518-98-3

1,1,2,2-tetrachloro-1,2-dimethyldisilane

1,1-dichlorotetramethyldisilane
4518-99-4

1,1-dichlorotetramethyldisilane

A

Dichloromethylsilane
75-54-7

Dichloromethylsilane

B

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

C

Methyltrichlorosilane
75-79-6

Methyltrichlorosilane

D

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

E

methylsilane
992-94-9

methylsilane

F

chloro-methyl-silane
993-00-0

chloro-methyl-silane

G

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

H

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

Conditions
ConditionsYield
With diethylene glycol dimethyl ether; lithium hydride at 60℃; for 0.25h; Sealed tube;
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

phenyllithium
591-51-5

phenyllithium

1,2-diphenyltetramethyldisilane
1145-98-8

1,2-diphenyltetramethyldisilane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; cyclohexane at 0 - 20℃; for 1h;100%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

2,2'-diindenyldimethylsilane lithium salt

2,2'-diindenyldimethylsilane lithium salt

dichlorotetramethyldisilane

dichlorotetramethyldisilane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -30℃; for 4h;99%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C12H18N(1-)*Li(1+)

C12H18N(1-)*Li(1+)

1,2-bis(2,6-diisopropylphenylamino)tetramethyldisilane
188599-46-4

1,2-bis(2,6-diisopropylphenylamino)tetramethyldisilane

Conditions
ConditionsYield
In diethyl ether at -35 - 20℃; for 12h; Inert atmosphere;98%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

2,2'-diindenyltetramethyldisilane lithium salt

2,2'-diindenyltetramethyldisilane lithium salt

C26H34Si4(2-)*2Li(1+)

C26H34Si4(2-)*2Li(1+)

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -30℃; for 4h;98%
1-methyl-o-carborane
16872-10-9

1-methyl-o-carborane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

1,2-bis(1'-methyl-o-carboranyl)-1,1,2,2-tetramethyl-1,2-disilane
668987-57-3

1,2-bis(1'-methyl-o-carboranyl)-1,1,2,2-tetramethyl-1,2-disilane

Conditions
ConditionsYield
With n-BuLi In diethyl ether; hexane; benzene (Ar); standard Schlenk technique; soln. of n-BuLi in hexane was added tosoln. of carborane in C6H6 at -78°C; mixt. was warmed to room te mp. and stirred for 2 h; transferred via cannula to suspn. of Si compd. (0.5 equiv.) in Et2O at -78°C; mixt. warmed to room temp.; stirred for 2 h; volatiles removed (vac.); residue dissolved in Et2O; filtered through silica gel; volatiles removed; crystd. (toluene, -5°C); elem. anal.;96%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

[1,1'-bis[tris(trimethylsilyl)silyl]ferrocenyldipotassium](18-crown-6)2*2C6H6

[1,1'-bis[tris(trimethylsilyl)silyl]ferrocenyldipotassium](18-crown-6)2*2C6H6

1,1'-ansa-[1,1,4,4-tetrakis(trimethylsilyl)-2,2,3,3-tetramethyltetrasilanylene]ferrocene
934822-73-8

1,1'-ansa-[1,1,4,4-tetrakis(trimethylsilyl)-2,2,3,3-tetramethyltetrasilanylene]ferrocene

Conditions
ConditionsYield
In tetrahydrofuran (N2); Schlenk technique; soln. of Fe complex in THF was added to soln. of Si compd. (1 equi.) in THF at -40°C; mixt. was warmed to room temp.; stirred for 12 h; aq. H2SO4 added; extd. (Et2O); org. layers dried (Na2SO4); solvent removed (vac.); residue treated with hot isopropanol; slowly cooled to room temp.; elem. anal.;96%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C12H24KO6(1+)*C13H39Si7(1-)
1231960-76-1

C12H24KO6(1+)*C13H39Si7(1-)

C30H90Si16
1231960-93-2

C30H90Si16

Conditions
ConditionsYield
In benzene for 2.25h;96%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

[bis(trimethylsilyl)((trimethylsilyl)methyl)silyl]potassium*18-crown-6

[bis(trimethylsilyl)((trimethylsilyl)methyl)silyl]potassium*18-crown-6

1,1,4,4-tetrakis(trimethylsilyl)-1,4-bis[(trimethylsilyl)methyl]-2,2,3,3-tetramethyltetrasilane
1314029-96-3

1,1,4,4-tetrakis(trimethylsilyl)-1,4-bis[(trimethylsilyl)methyl]-2,2,3,3-tetramethyltetrasilane

Conditions
ConditionsYield
In benzene at 0℃; for 2h;96%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

1,1,1,4,4,4-hexaphenyltetramethyltetrasilane
25368-92-7

1,1,1,4,4,4-hexaphenyltetramethyltetrasilane

Conditions
ConditionsYield
With lithium In toluene at -30 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;95%
Stage #1: Triphenylsilyl chloride With lithium In tetrahydrofuran at 0 - 20℃; for 10h;
Stage #2: 1,2-dichlorotetramethylsilane In tetrahydrofuran at 0 - 80℃; for 30h;
Stage #3: With water In hexane for 0.25h;
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

N,N’-Bis(2,6-diisopropylphenyl)-N-trimethylsilylformamidine
850816-27-2

N,N’-Bis(2,6-diisopropylphenyl)-N-trimethylsilylformamidine

trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

[(Me2SiNDipp)2CH]OTf
1441046-04-3

[(Me2SiNDipp)2CH]OTf

Conditions
ConditionsYield
Stage #1: 1,2-dichlorotetramethylsilane; N,N’-Bis(2,6-diisopropylphenyl)-N-trimethylsilylformamidine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; Inert atmosphere;
95%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

tris(trimethylsilyl)silyl potassium

tris(trimethylsilyl)silyl potassium

1,1,1,3,3,4,4,6,6,6-decamethyl-2,2,5,5-tetrakis(trimethylsilyl)-hexasilane
78365-62-5

1,1,1,3,3,4,4,6,6,6-decamethyl-2,2,5,5-tetrakis(trimethylsilyl)-hexasilane

Conditions
ConditionsYield
In toluene at -78 - 20℃; Inert atmosphere;95%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

tris(trimethylsilyl)germyl potassium

tris(trimethylsilyl)germyl potassium

2,2,5,5-tetrakis(trimethylsilyl)-2,5-digermadecamethylhexasilane
849441-04-9

2,2,5,5-tetrakis(trimethylsilyl)-2,5-digermadecamethylhexasilane

Conditions
ConditionsYield
In toluene at -78 - 20℃; Inert atmosphere;95%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

2,5-bis(trimethylsilyl)undecamethylhexasilan-2-yl potassium

2,5-bis(trimethylsilyl)undecamethylhexasilan-2-yl potassium

2,5,5,8,8,11-hexakis(trimethylsilyl)icosamethyldodecasilan

2,5,5,8,8,11-hexakis(trimethylsilyl)icosamethyldodecasilan

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 5h;95%
dichloromethyl[(trimethylsilyl)methyl]silane
16538-65-1

dichloromethyl[(trimethylsilyl)methyl]silane

pentamethylchlorodisilane
1560-28-7

pentamethylchlorodisilane

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

1-chloro-1,1,3,3,3-pentamethyldisiloxane
2943-62-6

1-chloro-1,1,3,3,3-pentamethyldisiloxane

Me3SiSiMe2OSiMe2H
56240-54-1

Me3SiSiMe2OSiMe2H

Conditions
ConditionsYield
Stage #1: dichloromethyl[(trimethylsilyl)methyl]silane; pentamethylchlorodisilane; 1,2-dichlorotetramethylsilane; 1-chloro-1,1,3,3,3-pentamethyldisiloxane With water at 80 - 90℃; for 3h;
Stage #2: perfluorobutanesulfonic acid at 100℃; for 3 - 4h; Heating / reflux;
94.8%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

bis(phenylthio)methane
3561-67-9

bis(phenylthio)methane

1,2-bis-(bis-phenylsulfanyl-methyl)-1,1,2,2-tetramethyl-disilane
218932-31-1

1,2-bis-(bis-phenylsulfanyl-methyl)-1,1,2,2-tetramethyl-disilane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - 20℃;94%
1-phenyl-1,2-closo-C2B10H11
16390-61-7

1-phenyl-1,2-closo-C2B10H11

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

1,2-bis(1'-phenyl-o-carboranyl)-1,1,2,2-tetramethyl-1,2-disilane
668987-58-4

1,2-bis(1'-phenyl-o-carboranyl)-1,1,2,2-tetramethyl-1,2-disilane

Conditions
ConditionsYield
With n-BuLi In diethyl ether; hexane; benzene (Ar); standard Schlenk technique; soln. of n-BuLi in hexane was added tosoln. of carborane in C6H6 at -78°C; mixt. was warmed to room te mp. and stirred for 2 h; transferred via cannula to suspn. of Si compd. (0.5 equiv.) in Et2O at -78°C; mixt. warmed to room temp.; stirred for 2 h; volatiles removed (vac.); residue dissolved in Et2O; filtered through silica gel; volatiles removed; crystd. (toluene, -5°C); elem. anal.;94%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

[(1,2-C2B10H10)Li2]*2Et2O

[(1,2-C2B10H10)Li2]*2Et2O

1,1,2,2-tetramethyl-3,4-[1,2-dicarba-closo-dodecaborano(12)]-1,3-disila-cyclobutane
220453-53-2

1,1,2,2-tetramethyl-3,4-[1,2-dicarba-closo-dodecaborano(12)]-1,3-disila-cyclobutane

Conditions
ConditionsYield
In diethyl ether suspn. of carborane deriv. in Et2O cooled to 0°C, (Me2SiCl)2 injected through syringe for 30 min; stirred for 3 h at room temp.; insol. material separated by centrifugation; remaining insol. residue washed with Et2O and centrifuged; solns. combined; liquid evapd. in vac.;94%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

2-methoxyphenyllithium
31600-86-9

2-methoxyphenyllithium

1,2-bis(2-methoxyphenyl)-1,1,2,2-tetramethyldisilane
332343-84-7

1,2-bis(2-methoxyphenyl)-1,1,2,2-tetramethyldisilane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;93%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

3,5-di-tert-butyl-4-trimethylsiloxyphenyllithium
79101-69-2

3,5-di-tert-butyl-4-trimethylsiloxyphenyllithium

1,2-bis-(3,5-di-tert-butyl-4-trimethylsilanyloxy-phenyl)-1,1,2,2-tetramethyl-disilane
653604-19-4

1,2-bis-(3,5-di-tert-butyl-4-trimethylsilanyloxy-phenyl)-1,1,2,2-tetramethyl-disilane

Conditions
ConditionsYield
In diethyl ether at 20℃; for 2h;93%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

octamethyl-1,4-dioxa-2,3,5,6-tetrasilacyclohexane
17865-73-5

octamethyl-1,4-dioxa-2,3,5,6-tetrasilacyclohexane

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether; water for 6h; Inert atmosphere; Schlenk technique; Sealed tube;92%
With water In pentane Glovebox; Inert atmosphere;80%
With water In diethyl ether; acetone for 2h;72%
With pyridine In various solvents at 20℃; for 1h;72%
With water
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

1,1-dibromomethane
74-95-3

1,1-dibromomethane

1,2-bis(bromomethyl)-1,1,2,2-tetramethyldisilane
33558-73-5

1,2-bis(bromomethyl)-1,1,2,2-tetramethyldisilane

Conditions
ConditionsYield
With n-butyllithium; lithium bromide In tetrahydrofuran; hexane at -78 - 20℃;92%
With n-butyllithium; lithium bromide In tetrahydrofuran; hexane at -78 - 20℃;69%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

lithium di-tert-butylstannide

lithium di-tert-butylstannide

1,1,4,4-tetra(tert-butyl)-tetramethyl-1,4-distanna-2,3-disilabutane
223565-67-1

1,1,4,4-tetra(tert-butyl)-tetramethyl-1,4-distanna-2,3-disilabutane

Conditions
ConditionsYield
In tetrahydrofuran (inert atmosphere); stirring (-50°C, 2 h); warming to -30°C, addn. of petroleum ether, stirring (30 min), warming to 0°C, addn. of oxygen-free water, phase sepn., drying (CaCl2, 12 h), filtration, solvent removal (vac.), recrystn. (n-hexane);92%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

2-bromoindene
10485-09-3

2-bromoindene

1,2-di(1H-inden-1-yl)-1,1,2,2-tetramethyldisilane
221392-72-9

1,2-di(1H-inden-1-yl)-1,1,2,2-tetramethyldisilane

Conditions
ConditionsYield
With magnesium In tetrahydrofuran; ethylene dibromide Cooling with ice;92%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

C22H66Li2P2Si10

C22H66Li2P2Si10

C26H78P2Si12

C26H78P2Si12

Conditions
ConditionsYield
In diethyl ether at -78℃; Inert atmosphere;92%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

benzoyl chloride
98-88-4

benzoyl chloride

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

Conditions
ConditionsYield
With triphenylphosphine91%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

4-phenoxyphenylmagnesium bromide
21473-02-9

4-phenoxyphenylmagnesium bromide

1-(4-phenoxyphenyl)-1,1,2,2-tetramethyldisilane

1-(4-phenoxyphenyl)-1,1,2,2-tetramethyldisilane

Conditions
ConditionsYield
Stage #1: 1,2-dichlorotetramethylsilane; 4-phenoxyphenylmagnesium bromide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
91%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

bis(trimethylsilyl)(triisopropylsilyl)silyl potassium

bis(trimethylsilyl)(triisopropylsilyl)silyl potassium

2,5-bis(triisopropylsilyl)-2,5-bis(trimethylsilyl)decamethylhexasilan

2,5-bis(triisopropylsilyl)-2,5-bis(trimethylsilyl)decamethylhexasilan

Conditions
ConditionsYield
In tetrahydrofuran for 6h;91%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

Lithium-tert-butyldimethylsilylamid
82135-41-9

Lithium-tert-butyldimethylsilylamid

C16H44N2Si4

C16H44N2Si4

Conditions
ConditionsYield
90%
1,2-dicarba-closo-dodecaborane(12)
16872-09-6

1,2-dicarba-closo-dodecaborane(12)

1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

1,2-bis(o-carboranyl)-1,1,2,2-tetramethyl-1,2-disilane
652995-44-3

1,2-bis(o-carboranyl)-1,1,2,2-tetramethyl-1,2-disilane

Conditions
ConditionsYield
With n-BuLi In tetrahydrofuran; diethyl ether; hexane (Ar); standard Schlenk technique; soln. of n-BuLi in hexane was added tosoln. of carborane in THF at -78°C; mixt. was warmed to room tem p. and stirred for 2 h; transferred via cannula to suspn. of Si compd. (0.5 equiv.) in Et2O at -78°C; mixt. warmed to room temp.; stirred for 2 h; volatiles removed (vac.); residue dissolved in Et2O; filtered through silica gel; volatiles removed; crystd. (toluene, -5°C); elem. anal.;90%
1,2-dichlorotetramethylsilane
4342-61-4

1,2-dichlorotetramethylsilane

1,1-diisopropyltrimethyldisilanylpotassium

1,1-diisopropyltrimethyldisilanylpotassium

2,2,5,5-tetraisopropyldecamethylhexasilane

2,2,5,5-tetraisopropyldecamethylhexasilane

Conditions
ConditionsYield
In benzene at 0 - 20℃;90%

4342-61-4Relevant articles and documents

The behaviour of medium-sized permethylated cyclosilanes towards SOCl2 and SOCl2-HC(OCH3)3

Jenkner, P.K.,Spielberger, A.,Hengge, E.

, p. 161 - 164 (1992)

Treatment of Si6Me12 with SOCl2 in various solvents gives α,ω-dichloropermethylpolysilanes (nSi = 2,3,4,6) at temperatures above 80 deg C.In contrast to an earlier report, treatment of the α,ω-dichloropermethylpolysilanes with HC(OCH3)3 in the presence of SOCl2 does not give Si6Me12.

-

Wojnowski,W. et al.

, p. 271 - 278 (1977)

-

Katalytische Hydrierung chlorhaltiger Disilane mit Tributylstannan

Herzog, U.,Roewer, G.,Paetzold, U.

, p. 143 - 148 (1995)

Partial hydrogenation of methylchlorodisilanes and hexachlorodisilane to methylchlorohydrogendisilanes and chlorohydrogendisilanes respectively, is possible by the use of tri-n-butylstannane.Electron-pair donators catalyse the hydrogenation reaction.The 29Si NMR chemical shifts and coupling constants 1JSiH of some new methylchlorohydrogendisilanes are reported.Keywords: Silicon; Catalysis; Partial hydrogenation

Synthesis of dichloro derivatives of linear and cyclic permethyloligosilanes and cyclolinear permethylpolysilane-siloxanes and permethylpolyoxysilane based on them

Chernyavskii, A. I.,Larkin, D. Yu.,Chernyavskaya, N. A.

, p. 175 - 180 (2002)

The reactions of dodecamethylcyclohexasilane with chlorides of I, II, IV-VI, and VIII Group metals were studied as a promising approach to the synthesis of functional oligosilanes. When cyclohexasilane reacts with metal chlorides without a solvent at elevated temperatures, the process is intensified and, in some cases, the selectivity of formation of chloro derivatives of linear and cyclic permethyloligosilanes increases. The cyclolinear permethylpolysilane-siloxanes were prepared by heterofunctional polycondensation of the resulting oligosilanes with bifunctional cyclic and linear permethyloligosiloxanes. Cyclolinear permethylpolyoxysilane was synthesized for the first time by the reaction of 1,3-dihydroxycyclo-hexasilane with 1,3-dichlorohexamethyltrisilane.

Making Use of the Direct Process Residue: Synthesis of Bifunctional Monosilanes

Sturm, Alexander G.,Santowski, Tobias,Schweizer, Julia I.,Meyer, Lioba,Lewis, Kenrick M.,Felder, Thorsten,Auner, Norbert,Holthausen, Max C.

supporting information, p. 8499 - 8502 (2019/06/13)

The industrial production of monosilanes MenSiCl4?n (n=1–3) through the Müller–Rochow Direct Process generates disilanes MenSi2Cl6?n (n=2–6) as unwanted byproducts (“Direct Process Residue”, DPR) by the thousands of tons annually, large quantities of which are usually disposed of by incineration. Herein we report a surprisingly facile and highly effective protocol for conversion of the DPR: hydrogenation with complex metal hydrides followed by Si?Si bond cleavage with HCl/ether solutions gives (mostly bifunctional) monosilanes in excellent yields. Competing side reactions are efficiently suppressed by the appropriate choice of reaction conditions.

PROCESS FOR THE PRODUCTION OF ORGANOHYDRIDOCHLOROSILANES FROM HYDRIDOSILANES

-

Page/Page column 45; 46, (2019/04/16)

The invention relates to a process for the manufacture of organomonosilanes bearing both hydrogen and chlorine substituents at the silicon atom by subjecting one or more organomonosilanes to the reaction with one or more di- or carbodisilanes in the presence of one or more compounds (C) acting as a redistribution catalyst, wherein at least one of the silanes has only hydrogen and organic residues at the silicon atoms.

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