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1066-45-1

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1066-45-1 Usage

Chemical Properties

WHITE CRYSTALS

Uses

Trimethyltin chloride is an organotin reagent widely used in transferring trimethylstannyl groups onto the substrates to synthesize various organostannanes. Trimethylstannyl compounds derived from this reagent, are extensively used in the palladium-catalyzed Stille coupling reactions.

General Description

Solid.

Reactivity Profile

TRIMETHYLTIN CHLORIDE is in the family of tin compounds widely used as stabilizers for plastics, additives to paint(as antifouling agents). Some have catalytic properties. Examples include butyl tin, dibutyl tin oxide. Their main hazard is associated with their high toxicity, in skin adsorption or inhalation.

Hazard

A deadly poison. A reproductive hazard.

Health Hazard

Different sources of media describe the Health Hazard of 1066-45-1 differently. You can refer to the following data:
1. (Non-Specific -- Tin Compounds, Organic) The material is an irritant to the skin and gastrointestinal tract. Contact may specifically damage the following target organs: central nervous system, eyes, liver, urinary tract, and skin.
2. Trimethyltin chloride and other organotin compounds are highly toxic by ingestion, inhalation, or skin contact. Trimethyltin chloride can cause irritation and burns of the skin and eyes. Organotin compounds can affect the central nervous system. The degree of toxicity is greatest for compounds with three or four alkyl groups attached to tin. Diand monoalkyltin compounds are moderately toxic. The toxicity diminishes as the size of the alkyl groups increases. Thus, the oral LD50s in rats are as follows: dimethyltin dichloride, 74 to 237 mg/kg; tributyltin chloride, 122 to 349 mg/kg; dibutyltin oxide, 487 to 520 mg/kg; trioctyltin chloride, >4000 mg/kg. Organotin compounds have been shown to cause reproductive effects in laboratory animals.

Fire Hazard

Different sources of media describe the Fire Hazard of 1066-45-1 differently. You can refer to the following data:
1. Not a significant fire hazard. Emits toxic fumes in fire.
2. When heated to decomposition, TRIMETHYLTIN CHLORIDE emits toxic fumes of chlorides. Avoid decomposing heat.

Flammability and Explosibility

Not a significant fire hazard. Emits toxic fumes in fire.

Safety Profile

A deadly poison by intravenous route. Experimental reproductive effects. See also TIN COMPOUNDS. When heated to decomposition it emits toxic fumes of Cl-.

Incompatibilities

Trimethyltin chloride and other organotin halides react with water to produce hydrogen halides. Organotin hydrides react with water to produce hydrogen gas, which is flammable and explosive.

Waste Disposal

Excess trimethyltin chloride or other organotin compound and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

Check Digit Verification of cas no

The CAS Registry Mumber 1066-45-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,6 and 6 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1066-45:
(6*1)+(5*0)+(4*6)+(3*6)+(2*4)+(1*5)=61
61 % 10 = 1
So 1066-45-1 is a valid CAS Registry Number.
InChI:InChI=1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9Sn.ClH/c1-4(2)3;/h1-3H3;1H/q+1;/p-1

1066-45-1 Well-known Company Product Price

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

  • (T0958)  Trimethyltin Chloride  >98.0%(GC)

  • 1066-45-1

  • 5g

  • 455.00CNY

  • Detail
  • TCI America

  • (T0958)  Trimethyltin Chloride  >98.0%(GC)

  • 1066-45-1

  • 25g

  • 1,340.00CNY

  • Detail
  • Alfa Aesar

  • (71166)  Trimethyltin chloride   

  • 1066-45-1

  • 2g

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (71166)  Trimethyltin chloride   

  • 1066-45-1

  • 10g

  • 595.0CNY

  • Detail
  • Alfa Aesar

  • (71166)  Trimethyltin chloride   

  • 1066-45-1

  • 50g

  • 2293.0CNY

  • Detail
  • Aldrich

  • (375187)  Trimethyltinchloridesolution  1.0 M in hexanes

  • 1066-45-1

  • 375187-100ML

  • 1,745.64CNY

  • Detail
  • Aldrich

  • (375187)  Trimethyltinchloridesolution  1.0 M in hexanes

  • 1066-45-1

  • 375187-4X25ML

  • 1,918.80CNY

  • Detail
  • Aldrich

  • (375195)  Trimethyltinchloridesolution  1.0 M in THF

  • 1066-45-1

  • 375195-100ML

  • 1,528.02CNY

  • Detail
  • Aldrich

  • (375195)  Trimethyltinchloridesolution  1.0 M in THF

  • 1066-45-1

  • 375195-4X25ML

  • 1,627.47CNY

  • Detail
  • Aldrich

  • (146498)  Trimethyltinchloride  

  • 1066-45-1

  • 146498-5G

  • 437.58CNY

  • Detail
  • Aldrich

  • (146498)  Trimethyltinchloride  

  • 1066-45-1

  • 146498-10G

  • 623.61CNY

  • Detail
  • Aldrich

  • (146498)  Trimethyltinchloride  

  • 1066-45-1

  • 146498-50G

  • 2,962.44CNY

  • Detail

1066-45-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name TRIMETHYLTIN CHLORIDE

1.2 Other means of identification

Product number -
Other names trimethyl tin chloride

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:1066-45-1 SDS

1066-45-1Synthetic route

tetramethylstannane
594-27-4

tetramethylstannane

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
With tin(IV) chloride at -20 - 60℃; for 16h; Inert atmosphere;100%
With hydrogenchloride In chloroform 4h boiling, under inflow of gaseous HCl;70%
With HCl In chloroform 4h boiling, under inflow of gaseous HCl;70%
trimethyl(dimesylamino)stannane
87293-07-0

trimethyl(dimesylamino)stannane

benzoyl chloride
98-88-4

benzoyl chloride

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

N,N-bis(methanesulfonyl)benzamide
120622-90-4

N,N-bis(methanesulfonyl)benzamide

Conditions
ConditionsYield
In dichloromethane reflux for 48 h; evapn. of solvent, pptn. of N-benzoyldimesylamine, isolation of (CH3)3SnCl from filtrate;A 100%
B n/a
trimethyl(dimesylamino)stannane
87293-07-0

trimethyl(dimesylamino)stannane

benzoyl chloride
98-88-4

benzoyl chloride

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

N,N-bis(methanesulfonyl)benzamide
120622-90-4

N,N-bis(methanesulfonyl)benzamide

Conditions
ConditionsYield
In dichloromethane reflux for 48 h; evapn. of solvent, pptn. of N-benzoyldimesylamine, isolation of (CH3)3SnCl from filtrate;A 100%
B n/a
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

bis(trimethyltin) sulfide
1070-91-3

bis(trimethyltin) sulfide

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
With triphenylphosphine In ethanol; acetone byproducts: Ni, triphenylphosphonium sulfide; dropwise addn. of an ethanolic soln. of NiCl2*6H2O to a stirred soln. of ((CH3)3Sn)2S and triphenylphosphine in acetone; refluxing;; filtration;;100%
tetramethylstannane
594-27-4

tetramethylstannane

tin(IV) chloride
7646-78-8

tin(IV) chloride

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
stirring overnight at 60°F, N2-atmosphere; distd. at 15 Torr;99%
molar ratio of (CH3)4Sn:SnCl4=3:1; distn.;
In neat (no solvent) react. Me4Sn with SnCl4 (3:1) at 130°C for 2 h; recrystn. from hexane;
tetramethylstannane
594-27-4

tetramethylstannane

phenyltin trichloride
1124-19-2

phenyltin trichloride

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

methylphenyltin(IV) dichloride
15649-26-0

methylphenyltin(IV) dichloride

Conditions
ConditionsYield
equimolar amts. of educts, 0°C, 1.5h;A 99%
B 85%
equimolar amts. of educts, 0°C, 1.5h;A 99%
B 85%
germanium(II) chloride dioxane

germanium(II) chloride dioxane

GeC6H10(Sn(CH3)3)2
186268-80-4

GeC6H10(Sn(CH3)3)2

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In benzene-d6 byproducts: germanium-contg. polymer; (Ar); stirring (20°C, 2 d);99%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

bis(trimethyltin) sulfide
1070-91-3

bis(trimethyltin) sulfide

A

nickel(II) sulfide

nickel(II) sulfide

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In water; acetone dropwise addn. of an aq. soln. of NiCl2*6H2O to a stirred soln. of ((CH3)3Sn)2S in acetone at room temp.; refluxing for 5 h;; filtration;;A 90%
B 99%
O,O-dimethylphosphorylsulfenyl chloride
13894-35-4

O,O-dimethylphosphorylsulfenyl chloride

trimethyl(allyl)stannane
762-73-2

trimethyl(allyl)stannane

A

S-allyl O,O-dimethyl phosphorothioate
66498-87-1

S-allyl O,O-dimethyl phosphorothioate

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In tetrachloromethane from -15 deg C to RT;A 97%
B n/a
In tetrachloromethane addn. of soln. of sulfenyl chloride to soln. of stannane in CCl4 with cooling (-15°C) and stirring, warming to room temp.; solvent removed, distilln., (1)H-NMR;A 97%
B n/a
(4-methoxyphenyl)trimethylstannane
940-00-1

(4-methoxyphenyl)trimethylstannane

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With trichlorophosphate at 50 - 70℃; for 3h;A n/a
B 96%
tetramethylstannane
594-27-4

tetramethylstannane

butyl-methyl-tin dichloride
15649-24-8

butyl-methyl-tin dichloride

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

butyl-dimethyl-tin chloride
15649-31-7

butyl-dimethyl-tin chloride

Conditions
ConditionsYield
3h, 75 to 85°C;A 96%
B 91%
3h, 75 to 85°C;A 96%
B 91%
bis(triphenylphosphine)nickel(II) chloride
14264-16-5, 53996-95-5, 62075-39-2, 39716-73-9

bis(triphenylphosphine)nickel(II) chloride

bis(trimethyltin) sulfide
1070-91-3

bis(trimethyltin) sulfide

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In ethanol byproducts: Ni, triphenylphosphonium sulfide, triphenylphosphine; a mixt. of ((CH3)3Sn)2S and ((C6H5)3P)2NiCl2 in ethanol was heated at 95-100°C for 10 h;; distn.;;95%
bis(trimethylstannyl)methane
16812-43-4

bis(trimethylstannyl)methane

dimethyltin dichloride
753-73-1

dimethyltin dichloride

A

bis(chlorodimethylstannyl)methane
83135-39-1

bis(chlorodimethylstannyl)methane

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In neat (no solvent) heated at 60°C for 12 h; distd. (12-15 Torr), recrystd. (C6H6); elem. anal.;A 95%
B n/a
2,2-bis(trimethylstannyl)propane
83135-43-7

2,2-bis(trimethylstannyl)propane

dimethyltin dichloride
753-73-1

dimethyltin dichloride

A

2,2-bis(chlorodimethylstannyl)propane
83135-44-8

2,2-bis(chlorodimethylstannyl)propane

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In neat (no solvent) 2,2-bis(trimethylstannyl)propane placed in flash with 2 mol of dimethyldichlorostannane, heated at 60°C overnight; stirred at 15-20 Torr, warmed at 0.01 Torr to 100°C, recrystd. (CCl4); elem. anal.;A 95%
B n/a
3,3-bis(trimethylstannyl)propyl ethyl sulfoxide
85294-03-7

3,3-bis(trimethylstannyl)propyl ethyl sulfoxide

dimethyltin dichloride
753-73-1

dimethyltin dichloride

3,3-bis(chlorodimethylstannyl)propyl ethyl sulfoxide
91230-55-6

3,3-bis(chlorodimethylstannyl)propyl ethyl sulfoxide

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In dichloromethane mixt. of the sulfoxide (6.7 mmol) and SnMe2Cl2 (13.5 mmol) in CH2Cl2 refluxed for 12 h; solvent removed (rotary evaporator); SnMe3Cl removed (0.01 torr, 60 °C); recrystn. (CCl4/hexane); elem. anal.; mol. wt. calc.: 486.6; mol. wt. found: 506.6 (isopiestic in CH2Cl2 at 22 °C);A 95%
B n/a
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

trimethyl(trifluoro-1-propynyl)stanane
19097-32-6

trimethyl(trifluoro-1-propynyl)stanane

A

1,1,1-trifluoro-3-trimethylsilyl-2-propyne
6618-09-3

1,1,1-trifluoro-3-trimethylsilyl-2-propyne

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide mixt. heating (80°C, 0.5 h); Si-compd. isolation (vac. distn., elem. anal., IR and NMR spectroscopy);A 92%
B n/a
di-tert-butyltin dichloride
19429-30-2

di-tert-butyltin dichloride

tris(trimethylstannyl)amine
1068-70-8

tris(trimethylstannyl)amine

A

bis(trimethylstannyl)(chloro-di-tert-butylstannyl)amine

bis(trimethylstannyl)(chloro-di-tert-butylstannyl)amine

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In dichloromethane (inert atmosphere); stirring (-78°C to room temp.); removal of CH2Cl2 and trapping Me3SnCl at -78°C by applying high vacuum, NMR monitoring;A 0%
B 92%
tetramethylstannane
594-27-4

tetramethylstannane

Ethylbutylzinndichlorid
15649-29-3

Ethylbutylzinndichlorid

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

n-Butyl-ethylmethyl-zinnchlorid
15649-32-8

n-Butyl-ethylmethyl-zinnchlorid

Conditions
ConditionsYield
4h, 120 to 130°C;A 91%
B 76%
4h, 120 to 130°C;A 91%
B 76%
trimethylphenoxystannane
1529-50-6

trimethylphenoxystannane

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

A

phenyl methanesulfonate
16156-59-5

phenyl methanesulfonate

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In tetrachloromethane Kinetics; Me3SnOPh refluxed for 5 h with MeSO2Cl in CCl4 / kinetics measured at 120-150°C; Me3SnCl not isolated; detected by NMR;A 91%
B n/a
In further solvent(s) Kinetics; educts dissolved in CH2Br2, sealed in glass tube, heated at 120-140°C; NMR anal.;
In dichloromethane Kinetics; educts dissolved in CH2Cl2, sealed in glass tube, heated at 130-160°C; NMR anal.;
In benzonitrile Kinetics; educts dissolved in PhCN, sealed in glass tube, heated at 120-140°C; NMR anal.;
In acetonitrile Kinetics; educts dissolved in MeCN, sealed in glass tube, heated at 100-130°C; NMR anal.;
O,O-dimethylphosphorylsulfenyl chloride
13894-35-4

O,O-dimethylphosphorylsulfenyl chloride

p-vinylbenzyltrimethylstannane
64268-27-5

p-vinylbenzyltrimethylstannane

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

O,O-dimethyl-S-<2--2-chloroethyl>thiophosphate

O,O-dimethyl-S-<2--2-chloroethyl>thiophosphate

Conditions
ConditionsYield
In diethyl ether addn. of P-compound in soln. to stirred soln. of stannane at -50-70°C; solvent removed, (CH3)3SnCl isolated, extn. with ether (5 times), solvent removed; elem. anal.;A 91%
B 87%
In chloroform addn. of P-compound in soln. to stirred soln. of stannane at -20-30°C over 0.5h; solvent removed, (CH3)3SnCl isolated, chromy. (silica gel, Rf 0.07, benzene:acetone 4:1); elem. anal.;A 48%
B 35%
In tetrachloromethane soln. of equimolar amts. of starting materials mixed at -20 and 20°C; not isolated, detd. by H-NMR;
In benzene-d6 soln. of equimolar amts. of starting materials or with stannane to sulfenyl ratio of 2:1 mixed at 10°C; not isolated, detd. by H-NMR;
trimethyl(trimethylstannanylethynyl)silane
16035-50-0

trimethyl(trimethylstannanylethynyl)silane

A

1,4-bis(trimethylsilyl)-1,3-butadiyne
4526-07-2

1,4-bis(trimethylsilyl)-1,3-butadiyne

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
With iron(III) chloride In tetrachloromethane; toluene at 25℃; for 1.5h;A 90%
B 90%
With iron(III) chloride In tetrachloromethane; cyclohexane byproducts: FeCl2; at 25°C for 1.5 h;A 90%
B n/a
hydrogenchloride
7647-01-0

hydrogenchloride

trimethyl(dimesylamino)stannane
87293-07-0

trimethyl(dimesylamino)stannane

A

dimesylamine
5347-82-0

dimesylamine

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In dichloromethane stream of HCl for 3 h, stirring for 1 h at 20°C; pptn. of dimesylamine, filtration, isolation of (CH3)3SnCl from filtrate;A n/a
B 90%
hydrogenchloride
7647-01-0

hydrogenchloride

trimethyl(dimesylamino)stannane
87293-07-0

trimethyl(dimesylamino)stannane

A

dimesylamine
5347-82-0

dimesylamine

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In dichloromethane stream of HCl for 3 h, stirring for 1 h at 20°C; pptn. of dimesylamine, filtration, isolation of (CH3)3SnCl from filtrate;A n/a
B 90%
SiF3SiHCl2
119895-84-0

SiF3SiHCl2

trimethylstannane
1631-73-8

trimethylstannane

A

F3SiSiH3
15195-26-3

F3SiSiH3

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In neat (no solvent) Warming of starting materials (in absence of solvent, vac. line) for 30 min to room temp.; Removal of Me3SnCl by passing the mixt. through a trap cooled to -95°C (toluene), IR and NMR identification of volatile resulting compd.;A 90%
B n/a
In neat (no solvent) Condensing of 1 equiv. of Si-compd. with 2 equiv. of Me3SnH at -196°C (vac. line, no solvent). React. is obsd. via F-NMR only after warming (0°C, 30 min), while at -10°C (25 min) no react. occurs.; After 1 h at 0°C peaks due to SiF3SiH2Cl and unreacted SiF3SiHCl2 disappear and Me3SnCl is removed by passing the mixt. through a trap cooled to -95°C (toluene).;A 90%
B n/a
tetrachloro(η-pentamethylcyclopentadienyl)tungsten(V)

tetrachloro(η-pentamethylcyclopentadienyl)tungsten(V)

trimethyltin fluoride
420-60-0

trimethyltin fluoride

A

[WF4(η5-C5Me5)]
175477-60-8

[WF4(η5-C5Me5)]

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In dichloromethane stoichiometric ratio, stirring (8 h, room temp.); evapn. (vac.), washing (n-hexane, toluene), drying (vac.); elem. anal.;A 89.5%
B n/a
In toluene stoichiometric ratio, stirring (5 d, room temp.); filtn., evapn. (vac.), washing (n-hexane), drying (vac.);A 86%
B n/a
1-trimethylsilyl-2-phenyl-2-trimethylstannyl-ethene
97607-44-8

1-trimethylsilyl-2-phenyl-2-trimethylstannyl-ethene

mercury dichloride

mercury dichloride

A

1-trimethylsilyl-2-phenyl-2-chloromercuri-ethene
156994-84-2

1-trimethylsilyl-2-phenyl-2-chloromercuri-ethene

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
With potassium fluoride In tetrahydrofuran Solid HgCl2 is added to a soln. of the ethene-compd. in THF at room temp. After 20 h stirring KF is added.; After filtn. and removal of the solvent the residue is sublimed at 80°C/10-E2 torr, giving a highly viscous oil; elem. anal.;A 89%
B n/a
1,1,1,2,2,3,3-heptafluoro-3-iodo-propane
754-34-7

1,1,1,2,2,3,3-heptafluoro-3-iodo-propane

(3,3-dimethyl-1-butynyl)trimethylstannane
34664-54-5

(3,3-dimethyl-1-butynyl)trimethylstannane

A

2,2,7,7-tetramethyl-octa-3,5-diyne
6130-98-9

2,2,7,7-tetramethyl-octa-3,5-diyne

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

C

5,5,6,6,7,7,7-heptafluoro-2,2-dimethyl-3-heptyne
126260-37-5

5,5,6,6,7,7,7-heptafluoro-2,2-dimethyl-3-heptyne

D

trimethylstannyl iodide
811-73-4

trimethylstannyl iodide

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;A 2-3
B <=2
C 88%
D n/a
bis-triphenylphosphine-palladium(II) chloride In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;A 2-3
B <=2
C 87%
D n/a
bis(benzonitrile)palladium(II) dichloride In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;A 2-3
B <=2
C 70%
D n/a
[WCl4(η5-C5Me4Et)]

[WCl4(η5-C5Me4Et)]

trimethyltin fluoride
420-60-0

trimethyltin fluoride

A

[WF4(η5-C5Me4Et)]
175477-61-9

[WF4(η5-C5Me4Et)]

B

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
In dichloromethane stoichiometric ratio, stirring (8 h, room temp.); evapn. (vac.), washing (n-hexane, toluene), drying (vac.); elem. anal.;A 88%
B n/a
In toluene stoichiometric ratio, stirring (5 d, room temp.); filtn., evapn. (vac.), washing (n-hexane), drying (vac.);A 80%
B n/a
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

sodium
7440-23-5

sodium

4-methoxy-N,N,N-trimethylbenzenaminium iodide
17310-99-5

4-methoxy-N,N,N-trimethylbenzenaminium iodide

(4-methoxyphenyl)trimethylstannane
940-00-1

(4-methoxyphenyl)trimethylstannane

Conditions
ConditionsYield
With methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of CH3OC6H4NMe3I; irradn. with stirring for30 min, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;100%
With para-dinitrobenzene; methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CH3OC6H4NMe3I; irradn. with stirring for 30 min, quenching by addn. of MeI inexcess; evapn. of ammonia, treatment with water, extn. with ether;34%
With methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, then addn. of CH3OC6H4NMe3I; holding in dark for 30 min; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;14%
With para-dinitrobenzene; methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CH3OC6H4NMe3I, holding in dark for 30 min, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;0%
1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

(2,3-dimethoxyphenyl)trimethylstannane
134952-94-6

(2,3-dimethoxyphenyl)trimethylstannane

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane BuLi in hexane added to stirred soln. of veratrole and TMEDA in Et2O at 0°C, warmed to 22°C, stirred 1h, cooled to -80°C, addn. of (CH3)3SnCl in Et2O, warmed to 22°C, after 90 min H2O was added, stirred (room temp. overnight); Et2O layer washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure, distn. (Kugelrohr, 110°C, 0.04 mmHg); elem. anal.;;100%
1,5-dihydro-s-indacene
70600-14-5

1,5-dihydro-s-indacene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

1-(trimethylstannyl)-1,5-dihydro-s-indacene
106161-63-1

1-(trimethylstannyl)-1,5-dihydro-s-indacene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane byproducts: LiCl; To a soln. of s-indacene in THF at -78°C n-BuLi in hexane was added, mixt. allowed to warm slowly to 5-10°C; this soln. was added to a soln. of Me3SnCl in hexane;; LiCl was filtered; solvent was removed in vac., oil was crystd. on standing; elem. anal.;;100%
2,2'-Bithiophene
492-97-7

2,2'-Bithiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

5,5'-bis(trimethylstannyl)-2,2'-bithiophene
143367-56-0

5,5'-bis(trimethylstannyl)-2,2'-bithiophene

Conditions
ConditionsYield
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 25℃; for 2h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -40 - 25℃; for 3h;
100%
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; for 0.583333h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane Inert atmosphere;
93%
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; for 1h;
90%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

sodium
7440-23-5

sodium

(4-cyanophenyl)trimethylammonium iodide
17311-01-2

(4-cyanophenyl)trimethylammonium iodide

(4-cyanophenyl)trimethylstannane
58666-77-6

(4-cyanophenyl)trimethylstannane

Conditions
ConditionsYield
With methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, then addn. of CNC6H4NMe3I; holding in dark for 0.08 h; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;100%
With methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of CNC6H4NMe3I; irradn. with stirring for 0.08 h, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;100%
With para-dinitrobenzene; methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CNC6H4NMe3I; holding in dark for 0.08 h; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;35%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

tetrabutyl-ammonium chloride
1112-67-0

tetrabutyl-ammonium chloride

.

.

Conditions
ConditionsYield
In water byproducts: KCl;100%
3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2-(1-trimethylstannyl-3-propynyloxy) tetrahydropyran
711029-24-2

2-(1-trimethylstannyl-3-propynyloxy) tetrahydropyran

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane (Ar); soln. of n-BuLi in hexane was added dropwise to soln. of alkyne inTHF at -78°C; mixt. was stirred at -78°C for 30 min; Sn c ompd. was added; mixt. was stirred for 30 min and slowly warmed from -78°C to -30°C; extd. (ether/H2O); aq. phase washed (ether); combined org. phase dried (MgSO4); filtered; concd.;100%
1-Bromo-2,4-dimethoxybenzene
17715-69-4

1-Bromo-2,4-dimethoxybenzene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

(2,4-dimethoxyphenyl)trimethylstannane
134952-91-3

(2,4-dimethoxyphenyl)trimethylstannane

Conditions
ConditionsYield
With magnesium In tetrahydrofuran aryl halide added to stirred suspn. of Mg turnings in THF (under N2), heated at reflux for 90 min, cooled to room temp., addn. of (CH3)3SnCl, stirred at room temp. for 2h;; partitioned between Et2O and H2O, aq. phase extd. with Et2O, organic phase washed with H2O, dried (MgSO4), filtered, concentrated under reduced pressure, filtered through deep pad of silica (THF/hexane (1:19)); elem. anal.;;100%
benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene
29150-63-8

benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2,5,8-tris(trimethylstannyl)benzo[1,2-b:3,4-b’:5,6-b’’]trithiophene
1289556-30-4

2,5,8-tris(trimethylstannyl)benzo[1,2-b:3,4-b’:5,6-b’’]trithiophene

Conditions
ConditionsYield
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene In tetrahydrofuran; hexane at 0 - 20℃; for 6h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
100%
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Schlenk technique;
94%
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Reflux;
82%
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at 0℃; Inert atmosphere;
75%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole
165190-76-1

4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole

4,7-bis(5-(trimethylstannyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole
1025451-57-3

4,7-bis(5-(trimethylstannyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole

Conditions
ConditionsYield
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With 2,2,6,6-tetramethylpiperidinyl-lithium
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃;
100%
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; for 12h;
89%
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃;
85%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

toluene
108-88-3

toluene

benzyl(trimethyl)tin
4314-94-7

benzyl(trimethyl)tin

Conditions
ConditionsYield
Stage #1: toluene With (-)-sparteine at -78℃;
Stage #2: With n-butyllithium at -78 - 20℃; for 0.5h;
Stage #3: trimethyltin(IV)chloride at -78℃; for 2h;
100%
C21H24O2S3

C21H24O2S3

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

C24H32O2S3Sn

C24H32O2S3Sn

Conditions
ConditionsYield
Stage #1: C21H24O2S3 With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;
100%
2-(2-ethylhexyl)thiophen
4891-44-5

2-(2-ethylhexyl)thiophen

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

(5-(2-ethylhexyl)thiophen-2-yl)trimethylstannane
1429306-71-7

(5-(2-ethylhexyl)thiophen-2-yl)trimethylstannane

Conditions
ConditionsYield
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Schlenk technique;
100%
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
86.5%
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
0.68 g
3-hexylthiophene
1693-86-3

3-hexylthiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

(3-hexylthiophene-5-yl)trimethylstannane
154717-22-3

(3-hexylthiophene-5-yl)trimethylstannane

Conditions
ConditionsYield
Stage #1: 3-hexylthiophene With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; for 14h;
100%
Stage #1: 3-hexylthiophene With lithium diisopropyl amide
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃;
98%
Stage #1: 3-hexylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane for 1h; Reflux; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 2h;
92%
Stage #1: 3-hexylthiophene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 4h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
82.4%
With lithium diisopropyl amide
7-bromo-N,N-bis(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine

7-bromo-N,N-bis(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

N,N-bis(4-methoxyphenyl)-4'-(trimethylstannyl)biphenyl-4-amine

N,N-bis(4-methoxyphenyl)-4'-(trimethylstannyl)biphenyl-4-amine

Conditions
ConditionsYield
Stage #1: 7-bromo-N,N-bis(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere;
100%
N,N-bis(4-methoxyphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophen-6-amine

N,N-bis(4-methoxyphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophen-6-amine

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

N,N-bis(4-methoxyphenyl)-4,4-dimethyl-2-(trimethylstannyl)-4H-indeno[1,2-b]thiophen-6-amine

N,N-bis(4-methoxyphenyl)-4,4-dimethyl-2-(trimethylstannyl)-4H-indeno[1,2-b]thiophen-6-amine

Conditions
ConditionsYield
Stage #1: N,N-bis(4-methoxyphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophen-6-amine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere;
100%
4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene

4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2,6-bis(trimethylstannyl)-4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene

2,6-bis(trimethylstannyl)-4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene

Conditions
ConditionsYield
Stage #1: 4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene With n-butyllithium In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere; Glovebox;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran for 0.00277778h; Glovebox;
100%
4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-4H-dithieno[3,2-b:2',3'-d]pyrrole

4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-4H-dithieno[3,2-b:2',3'-d]pyrrole

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-2,6-bis(trimethylstannyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole

4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-2,6-bis(trimethylstannyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole

Conditions
ConditionsYield
Stage #1: 4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-4H-dithieno[3,2-b:2',3'-d]pyrrole With n-butyllithium In tetrahydrofuran at -78 - 5℃; for 3h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃; for 5h;
100%
2-(3,4,5-tris(dodecyloxy)phenyl)thiophene
1329426-09-6

2-(3,4,5-tris(dodecyloxy)phenyl)thiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2-(3,4,5-tridodecyloxyphenyl)-5-trimethylstannylthiophene
1329426-11-0

2-(3,4,5-tridodecyloxyphenyl)-5-trimethylstannylthiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -40℃;100%
2-hexylthieno[3,2-b]thiophene

2-hexylthieno[3,2-b]thiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

5′-hexyl-2,2′-bithiophene-5-trimethylstannane
1595320-51-6

5′-hexyl-2,2′-bithiophene-5-trimethylstannane

Conditions
ConditionsYield
Stage #1: 2-hexylthieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃;
100%
2-bromo-5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophene

2-bromo-5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

(5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophen-2-yl)trimethylstannane

(5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophen-2-yl)trimethylstannane

Conditions
ConditionsYield
Stage #1: 2-bromo-5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane
100%
2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane
773093-00-8

2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

C14H18O2S2Sn

C14H18O2S2Sn

Conditions
ConditionsYield
Stage #1: 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane With n-butyllithium In tetrahydrofuran; water at -78 - 0℃; for 2h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; water at -78 - 20℃; Inert atmosphere;
99.9%
Stage #1: 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
99.8%
2-(2'-butyl-1'-octyl)thiophene
1271438-65-3

2-(2'-butyl-1'-octyl)thiophene

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

2-(2-butyloctyl)-5-trimethylstannylthiophen
1362165-84-1

2-(2-butyloctyl)-5-trimethylstannylthiophen

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran99.2%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

(S)-2-(2-Methylbutyl)thiophene
73893-87-5

(S)-2-(2-Methylbutyl)thiophene

(S)-2-(2-methylbutyl)-5-trimethylstannylthiophene
1362166-27-5

(S)-2-(2-methylbutyl)-5-trimethylstannylthiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran99.1%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

1-tert-butyldimethylsilyl-3-trimethylstannyl-7-azaindole
226085-20-7

1-tert-butyldimethylsilyl-3-trimethylstannyl-7-azaindole

Conditions
ConditionsYield
Stage #1: 3-bromo-1-(tert-butyldimethylsilyl)-1H-pyrrolo[2,3-b]pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -90℃; for 0.0833333h;
Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; pentane at -90℃; for 1h;
99%

1066-45-1Relevant articles and documents

Kraus, C. A.,Greer, W. N.

, p. 2629 - 2633 (1922)

Alkyl- and acyl-substituted vinylstannanes: Synthesis and reactivity in electrophilic substitution reactions

Cochran, John C.,Prindle, Vicki,Young, Heather A.,Kumar, Mark H.,Tom, Samson,Petraco, Nicholas D. K.,Mohoro, Clare,Kelley, Brendan

, p. 885 - 902 (2002)

Six substituted vinylstannanes have been prepared. (E)- and (Z)-2-trimethylstannyl-2-butene, (1) and (2), respectively, 2-methyl-1-(trimethylstannyl) propene, (3), and 3-methyl-2-trimethylstannyl-2-butene, (4), were prepared by coupling the appropriate lithium or Grignard reagent with chlorotrimethylstannane. 3-Trimethylstannyl-3-butene-2-one, (5), and (Z)-3-trimethylstannyl-3-hexene-2-one, (6), were prepared by palladium(O) catalyzed hydrostannation of the appropriate ynone. This reaction was regiospecific such that the trimethylstannyl and carbonyl groups were bonded at the same vinyl carbon. The reaction was also stereospecific giving syn addition in each case. However, isomerization to a mixture of isomers was observed for the reaction of (5) with Me3SnD and complete isomerization of E-(6) to Z-(6). Each compound was characterized by 1H, 13C, and 119Sn NMR. The reactivity to protodestannylation was determined for each compound by spectrophotometric measurement of second order rate constants. The reactivity of the multimethyl-substituted vinylstannanes was consistent with the reactivity determined previously for monomethyl-substituted vinylstannanes. However, two methyl groups at the remote vinyl carbon exhibited a synergistic activating effect on the protodestannylation reactivity. The acyl group was found to be deactivating for protodestannylation. The stereochemistry of the reaction was round to take place with retention of configuration.

Synthesis and reactivity of germanium heterocycles containing germanium - tin bonds

Nosov,Lalov,Borovik,Lee,Egorov,Nefedov

, p. 2623 - 2626 (1996)

Previously unknown stannyl-substituted germanium heterocycles, 1,1-bis(trimethylstannyl)-2,3,4,5-tetraphenyl-1-germacyclopenta-2,4-diene and 1,1-bis(trimethylstannyl)-3,4-dimethyl-1-germacyclopent-3-ene were synthesized, and their photolysis and chemical

Tombe, F. J. A. des,Kerk, G. J. van der,Noltes, J. G.

, p. 173 - 180 (1973)

Reagents based on cyclopentadienyl derivatives of the group 14 elements for the synthesis of indium(I) derivatives. Crystal and molecular structure of in(C5H4SiMe3)

Beachley Jr.,Lees,Glassman,Churchill, Melvyn Rowen,Buttrey, Lisa A.

, p. 2488 - 2492 (1990)

Cyclopentadienyl trimethyl derivatives of the group 14 elements (C5H4MMe3, M = Si, Ge, Sn) have been investigated for their effects on indium(I) chemistry. The compounds In(C5H4SiMe3) and In(C5H4GeMe3) have been prepared from the corresponding lithium cyclopentadienyl reagent LiC5H4MMe3 and InCl. Characterization data have included partial elemental analyses (C, H), physical properties, IR and 1H NMR spectroscopic data, oxidation reactions with dilute aqueous HCl, and a single-crystal X-ray structural study in the case of In(C5H4SiMe3). When cyclopentadienyltrimethyltin, C5H5SnMe3, was combined with InCl in diethyl ether, In(C5H5) and Me3SnCl were formed in good yields. In(C5H4SiMe3) crystallizes in the centrosymmetric monoclinic space group P21/c (C2h5; No. 14) with a = 9.171 (5) ?, b = 9.910 (6) ?, c = 11.677 (7) ?, β = 97.30 (5)°, V = 1052.6 (11) ?3, and Z = 4. Diffraction data (Mo Kα radiation, 2θ = 4.5-50.0°) were collected on a Syntex P21 automated four-circle diffractometer, and the structure was solved and refined to RF = 5.0% and RwF = 4.0% for all 1851 independent reflections (RF = 3.1% and RwF = 3.5% for those 1336 data with |Fo| > 6σ|Fo|)). The solid-state structure consists of infinite zigzag chains of [In(C5H4SiMe3)]∞. Each indium atom interacts with two η5-C5H4SiMe3 ligands with a centroid?In?centroid angle of 131.78°, and each η5-C5H4SiMe3 ligand is linked to two indium atoms with In?centroid?In angles of 175.94°. There are no short interstrand In?In interactions, the shortest such distance being 5.428 ?. Thus, In(C5H4SiMe3) is the first cyclopentadienylindium(I) derivative with no apparent indium-indium interactions.

Homolytic Substitution at Carbon: 1,3- and 1,5-Ring Closures in Organotin-Substituted Radicals

Davis, Dennis D.,Ahmed, Fahim U.

, p. 7653 - 7654 (1981)

-

Abel et al.

, p. 260,261 (1966)

Berghe, E. V. van den,Kelen, G. P. van der

, p. 522 - 527 (1966)

Investigation of the catalyst system tungsten hexachloride/tetramethyltin; reduction of tungsten hexachloride during the alkylation step

Thorn-Csanyi, E.,Kessler, M.

, p. 253 - 260 (1991)

The alkylation steps in the catalyst system tungsten hexachloride/tetramethyltin have been studied kinetically. FTIR examinations in combination with UV and GC results have shown that the alkylation of tungsten hexachloride is accompanied by a reduction of the tungsten component. Ether addition increases the amount of the tungsten chloride which is reduced.

Kato, S.,Kato, T.,Mizuta, M.,Itoh, K.,Ishii, Y.

, p. 167 - 171 (1973)

Eaborn, C.,Najam, A. A.,Walton, D. R. M.

, (1972)

Ssebuwufu, P. John,Glockling, F.,Harriott, P.

, p. L35 - L38 (1985)

Cardin et al.

, p. C70 (1973)

Kozuka,Naribayashi

, p. 3638 (1979)

Simple procedure for conversion of a trialkyltin fluoride into the corresponding chloride or bromide

Mitchell, Terence N.,Kwetkat, Klaus,Godry, Bernd

, p. 1633 - 1634 (1991)

Trialkyltin fluorides are converted into the chlorides or bromides on treatment with an excess of the corresponding sodium halide in tetrahydrofuran.

Armbrecht,jun. et al.

, p. 3218 (1969)

Redox properties of dihalogermylenes, dihalostannylenes and their complexes with Lewis bases

Lee, V.Ya.,Basova, A.A.,Matchkarovskaya, I.A.,Faustov, V.I.,Egorov, M.P.,et al.

, p. 27 - 34 (1995)

Reduction and oxidation potentials of Gel2, GeBr2 * B (B = dioxane, PPh3), GeCl2 * B (B = dioxane, PPh3, AsPh3, Py, dip), SnCl2 * dioxane, SnX2 (X = F, Cl Br, I) were measured in MeCN at 20 deg C.The data obtained indicate that in many cases the EX2 and EX2 * B (E = Ge, Sn) can act not only as a good reducing agents, but also as strong oxidants.Examples of redox reactions in which EX2 and EX2 * B react as oxidizing agents were found.The variation of the redox potentials of the dihalogermylenes and dihalostannylenes with complexation and with the nature of the halogen substituent and the Lewis base is discussed.In some cases (GeI2, GeX2 * B; X = Cl, Br, B = dioxane, PPh3), the reduction or oxidation was found to be quasi-reversible, indicating the presence of relatively stable ion radicals.AM1 calculations on GeCl2 * dioxane and GeCl2 * PH3 complexes show that the complexation destabilizes both the highest occupied and the lowest unoccupied MOs of the carbene analogues.The complexation reduces the IP and lowers the oxidation potential; its intluence on the electron affinity is not straightforward.Calculations of the ion radicals of GeCl2 and GeCl2 * B (B = dioxane, PH3 ) show that in the ground state an unpaired electron occupies ?-MO in the cation and ?-MO in anion radicals.Keywords: Germanium; Tin; Germylenes; Stannylene; Electrochemistry; AM1 calculations

Conversion of Alkyltantalum Chlorides to Fluorides Using Trimethyltin Fluoride as a Fluorinating Agent. Crystal Structures of (p-MeC6H4CH2)3TaF2, (Me3SnCl.Me3SnF.TaF5)n, (Me3Si)2CHTaCl4

Guzyr, Olexandr I.,Schormann, Mark,Schimkowiak, Jürgen,Roesky, Herbert W.,Lehmann, Christopher,Walawalkar, Mrinalini G.,Murugavel, Ramaswarny,Schmidt, Hans-Georg,Noltemeyer, Mathias

, p. 832 - 836 (1999)

The reactions of alkyltantalum chlorides with trimethyltin fluoride were found to be highly dependent on the number of organic ligands on tantalum as well as on the electronic and the steric nature of the substituants. The synthesis of trialkyltantalum difluorides of general formula (RCH2)3TaF2 (R = Ph, 1; R = p-Tol, 2; R = Me3Si, 3) and the first example of the alkyltantalum tetrafluoride (Me3Si)2CHTaF4 (8) are reported. The compounds (p-MeC6H4-CH2)3TaF2, (Me2SnCl.Me3SnFTaF5)n (Me3Si)2CHTaCl4, {(Me3Si)2CHTaCl4(Me3Si) 2CH]2Ta2-Cl6μ2-O)}, and (Me3Si)2CHTaF4 respectively have been characterized by single-crystal X-ray structural analysis.

STUDY OF THE REDISTRIBUTION REACTION OF TETRAMETHYLTIN WITH DIMETHYLTIN DICHLORIDE IN SEVERAL APROTIC SOLVENTS.

Yamashita,Saito,Yoshino,Takahashi

, p. 2555 - 2558 (1983)

The redistribution reaction of tetramethyltin with dimethyltin dichloride was studied in eight aprotic solvents by using the **1H NMR technique. The second-order rate constant of the reaction (ln k//2) is proportional to the dielectric constant of the solvent. There is a weak relation between the rate constants (ln k//2) and the values of **2J(Sn-H) of Me//2SnCl//2 in several solvents, which are considered to be related to the coordination ability of the solvents. The rate constants are also related to Kosower's Z values of the solvents. The activation entropies of the reaction in four typical solvents have large negative values. This predicts that the reaction proceeds via a four-center transition state.

MECHANISM OF THE REACTION OF (ARYLOXY)TRIMETHYLSTANNANE WITH METHANESULFONYL CHLORIDE - SOLVENT AND SUBSTITUENT EFFECTS ON THE RATE OF THE REACTION.

Kozuka,Yamaguchi,Tagaki

, p. 573 - 576 (1983)

A kinetic study has been conducted on the reactions of (aryloxy)trimethylstannanes with methanesulfonyl chloride giving chlorotrimethylstannane and aryl methanesulfonates. The reaction was found to obey a second order kinetic equation. The solvent effect on the rate of the reaction appeared obscure although a small rate enhancement was observed in a polar solvent. Substituent effect of the aryloxyl group was found to be dependent on the solvent used while a clear isokinetic relationship was observed. A charge separated four-center transition state has been suggested for the reaction.

Jean,Guillerm,Lequan

, p. P1-P2 (1970)

Platinum-catalyzed phenyl and methyl group transfer from tin to iridium: Evidence for an autocatalytic reaction pathway with an unusual preference for methyl transfer

Smith, Stuart E.,Sasaki, Jennifer M.,Bergman, Robert G.,Mondloch, Joseph E.,Finke, Richard G.

, p. 1839 - 1841 (2008)

Platinum complexes have been found to catalyze the transfer of σ-bound ligands to the Ir center in Cp*(PMe3)IrCl2 (Cp* = η5-C5Me5) from Bu3SnPh and PhxSnMe

Roberts, R. M. G.

, p. 323 - 330 (1971)

A utility for organoleads: Selective alkyl and aryl group transfer to tin

Arias-Ugarte, Renzo N.,Pannell, Keith H.

, p. 1703 - 1708 (2018/02/09)

Me4Pb and Ph4Pb readily transfer methyl or phenyl groups to an equivalent molar ratio of tin(iv) chlorides in the order SnCl4 > MeSnCl3 > Me2SnCl2 > Me3SnCl, often in a selective manner. Me3PbCl and Ph3PbCl specifically transfer a single methyl/phenyl group under the same reaction conditions to produce recovered yields in >75%. Specific transfer of 2 methyl groups from PbMe4 can be achieved at elevated temperatures and/or a 2:1 molar ratio Pb:Sn.

Direct Detection, Dimerization, and Chemical Trapping of Dimethyl- and Diphenylstannylene from Photolysis of Stannacyclopent-3-enes in Solution

Duffy, Ian R.,Leigh, William J.

, p. 5029 - 5044 (2015/11/09)

Dimethyl- and diphenylstannylene (SnMe2 and SnPh2, respectively) have been successfully detected and characterized in solution. The stannylenes were generated by photolysis of 1,1,3-trimethyl-4-phenyl- (2) and 3,4-dimethyl-1,1-diphenylstannacyclopent-3-ene (3), respectively, which have been shown to extrude the species cleanly and in high (0.6 2SnCl2) as the stannylene substrate. Laser flash photolysis of 2 and 3 in deoxygenated hexanes affords promptly formed transient absorptions assigned to SnMe2 (λmax = 500 nm; ε500 = 1800 ± 600 M-1 cm-1) and SnPh2 (λmax = 290, 505 nm; ε500 = 2500 ± 600 M-1 cm-1), respectively, which decay with absolute second-order rate constants within a factor of 2 of the diffusional limit in both cases. The decay of the stannylenes is accompanied by the growth of new transient absorptions ascribable to the corresponding dimers, the structures of which are assigned with the aid of DFT and time-dependent (TD) DFT calculations at the (TD)ωB97XD/6-31+G(d,p)C,H,O-LANL2DZdpSn level of theory. Dimerization of SnMe2 affords a species exhibiting λmax = 465 nm, which is assigned to the expected Sn=Sn doubly bonded dimer, tetramethyldistannene (Me2Sn=SnMe2, 16a), in agreement with earlier work. In contrast, the spectrum of the dimer formed from SnPh2 exhibits strong absorptions in the 280-380 nm range and a very weak absorption at 650 nm, on the basis of which it is assigned to phenyl(triphenylstannyl)stannylene (17b). The calculations suggest that 17b is formed via ultrafast rearrangement of a novel phenyl-bridged stannylidenestannylene intermediate (20), which can be formed either directly by "endo" dimerization of SnPh2 or by isomerization of the "exo" dimer, tetraphenyldistannene (16b); the predicted barriers for these rearrangements are consistent with the experimental finding that the observed product is formed at close to the diffusion-controlled rate. Absolute rate and equilibrium constants are reported for the reactions of SnMe2 and SnPh2 with Me2SnCl2 and methanol (MeOH), respectively, in hexanes at 25 °C.

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