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Chlorotributyltin
Cas No: 1461-22-9
USD $ 1.0-1.0 / Gram 1 Gram 1 Metric Ton/Month Nanjing chemipioneer pharmaceutical & technology Co., LTD Contact Supplier
Amadis Chemical offer CAS#1461-22-9;CAT#A808453
Cas No: 1461-22-9
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
Factory Supply Tri-n-butyltin chloride
Cas No: 1461-22-9
No Data 100 Gram 4000 Metric Ton/Day Ality Chemical Corporation Contact Supplier
TIANFU-CHEM - Chlorotributyltin
Cas No: 1461-22-9
No Data 1 Kilogram 10 Metric Ton/Month Henan Tianfu Chemical Co., Ltd. Contact Supplier
Pharmaceutical Grade CAS 1461-22-9 with competitive price
Cas No: 1461-22-9
USD $ 139.0-210.0 / Kilogram 1 Kilogram 1000 Kilogram/Day Zhuozhou Wenxi import and Export Co., Ltd Contact Supplier
Chlorotributyltin CAS No.:1461-22-9
Cas No: 1461-22-9
USD $ 4.0-100.0 / Gram 10 Gram 1000 Metric Ton/Week HUBEI AOKS BIO-TECH CO.,LTD Contact Supplier
Chlorotributyltin CAS NO.1461-22-9
Cas No: 1461-22-9
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Chlorotributyltin CAS NO.1461-22-9
Cas No: 1461-22-9
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Chlorotributyltin;Tributyltin Chloride;TBTC CAS:1461-22-9 from FandaChem
Cas No: 1461-22-9
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Chlorotributyltin (High quality and competitive produc
Cas No: 1461-22-9
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1461-22-9 Usage

Uses

Tributyltin Chloride is a triorganotin compound with insecticidal acitivity. Tributyltin Chloride is an endocrine disruptor as well as an inhibitor for the V-ATPases (potential targets in the treatmen t of diseases such as osteoporosis and cancer).

Description

Chlorotributyltin is the chloride of tributyltin. It is a biocide that contaminates foods, especially shellfish. It is an endocrine disrupter in several marine species and is neurotoxic and immuno-toxic in mammals. It has been used as a heat stabilizer, agricultural pesticide and component of antifouling paints2. However, it is perhaps the most acutely toxic chemical to aquatic organisms ever deliberately introduced to water. It has been demonstrated to have an adverse effect on shellfish in France and England, and as a consequence the use of tributyltin‐containing antifouling paints has been restricted in these countries. Other countries have banned the use of tributyltin‐containing antifouling paints or are contemplating restrictions3.

References

  1. Cooke, G. M., et al. Food & Chemical Toxicology An International Journal Published for the British Industrial Biological Research Association 42.2(2004):211-220.
  2. Nakatsu, Yusuke, Y. Kotake, and S. Ohta. "Tributyltin-induced cell death is mediated by calpain in PC12 cells."Neurotoxicology 27.4(2006):587-593.
  3. Maguire, R. James. "Environmental aspects of tributyltin." Applied Organometallic Chemistry 1.6(1987):475-498.
InChI:InChI=1/3C4H9.ClH.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H;/q;;;;+1/p-1/rC12H27Sn.ClH/c1-4-7-10-13(11-8-5-2)12-9-6-3;/h4-12H2,1-3H3;1H/q+1;/p-1

1461-22-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A10746)  Tri-n-butyltin chloride, 96%    1461-22-9 1000g 2716.0CNY Detail
Alfa Aesar (A10746)  Tri-n-butyltin chloride, 96%    1461-22-9 250g 987.0CNY Detail
Alfa Aesar (A10746)  Tri-n-butyltin chloride, 96%    1461-22-9 50g 283.0CNY Detail
TCI America (T0363)  Tributyltin Chloride  >97.0%(T) 1461-22-9 500g 1,480.00CNY Detail
TCI America (T0363)  Tributyltin Chloride  >97.0%(T) 1461-22-9 100g 595.00CNY Detail
TCI America (T0363)  Tributyltin Chloride  >97.0%(T) 1461-22-9 25g 235.00CNY Detail

1461-22-9Synthetic route

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

phosphorus pentachloride

(Benzoyloxy)tributylstannan
4342-36-3

(Benzoyloxy)tributylstannan

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
byproducts: C6H5COCl;100%
n-Butyl chloride
109-69-3

n-Butyl chloride

A

dibutyltin chloride
683-18-1

dibutyltin chloride

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
With catalyst: dicyclohexyl-18-crown-6/n-C4H9I In N,N-dimethyl-formamide 120°C; 24 h; excess KI;; analyzed by GLC;;A 99%
B 1%
With catalyst: dibenzo-18-crown-6/n-C4H9I In N,N-dimethyl-formamide 120°C; 24 h; excess KI;; analyzed by GLC;;A 98%
B 2%
With catalyst: dibenzo-18-crown-6/n-C8H17I In N,N-dimethyl-formamide 120°C; 24 h; excess KI;; analyzed by GLC;;A 98%
B 2%
allyltributylstanane
24850-33-7

allyltributylstanane

tantalum pentachloride
7721-01-9

tantalum pentachloride

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In acetonitrile N2; equimol., or 2, or 3 equiv. of Sn compd., stirred at -40°C for 5-30 min; NMR, chromy.;99%
In tetrahydrofuran equimol., stirred at -40°C for 5-30 min; NMR, chromy.;16%
bis(cyclopentadienyl)vanadium dichloride
12083-48-6

bis(cyclopentadienyl)vanadium dichloride

tributylstannyl isothiocyanate
5035-65-4

tributylstannyl isothiocyanate

A

bis(η5-cyclopentadienyl)vanadium diisothiocyanate

bis(η5-cyclopentadienyl)vanadium diisothiocyanate

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In toluene molar ratio V-complex/Bu3SnNCS=1:2, evacuated sealed ampul (20°C, 120 h);A 99%
B 84.5%
In toluene Heating at 20°C for 120 h.;A 99%
B 85.5%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

bis(tributylstannyl)carbodiimide
34885-41-1

bis(tributylstannyl)carbodiimide

A

bis(trimethylsilyl)carbodi-imide
1000-70-0

bis(trimethylsilyl)carbodi-imide

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In neat (no solvent) isolation from atmosphere; heating (20 - 160°C, 1 - 2 h); distn.;A 93.5%
B 98%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

dichlorodiphenylgermane
1613-66-7

dichlorodiphenylgermane

A

diphenylgermane
1675-58-7

diphenylgermane

B

tributyltin chloride
1461-22-9

tributyltin chloride

C

diphenylgermylene
68816-03-5

diphenylgermylene

D

diphenylchlorogermane
7366-23-6

diphenylchlorogermane

Conditions
ConditionsYield
In neat (no solvent) byproducts: N2, ClCH2CO2CH2CH3; 1 equiv of diazoester adding slowly to an equimolar mixt. of Ge and Sn deriv. to result in an exothermic reaction with N2 evolution; allowing to stand for 24 h at 20°C; analyzed by gas chromy. and NMR spectroscopy;A 33%
B 97%
C 15-20
D 7%
2-chloro-[1,3,2]dioxaborolane
1192-03-6

2-chloro-[1,3,2]dioxaborolane

2-methylallyltributyltin
67883-62-9

2-methylallyltributyltin

A

2-(2-methyl-2-propenyl)-1,3,2-dioxaborolane
74348-95-1

2-(2-methyl-2-propenyl)-1,3,2-dioxaborolane

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In dichloromethane (N2); to soln. of B compd. was dropped soln. of Sn compd. within 20 minat -10°C; mixt. was sepd. by fractionated distn. in vac.; elem. anal.;A 87%
B 97%
ethyl tributylstannyltriethylsilyl acetate

ethyl tributylstannyltriethylsilyl acetate

dibutylchloroborane
1730-69-4

dibutylchloroborane

A

trimetylsilylketene
4071-85-6

trimetylsilylketene

B

dibutylborinic acid methyl ester
2344-21-0

dibutylborinic acid methyl ester

C

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In pentane -50°C; fractionation;A 57%
B 82%
C 96%
hydrogenchloride
7647-01-0

hydrogenchloride

formaldehyd
50-00-0

formaldehyd

phosphorus

phosphorus

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

tetrakis(hydroxymethyl)phosphonium chloride
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

Conditions
ConditionsYield
Stage #1: phosphorus; tri-n-butyl-tin hydride In toluene at 20℃; for 16h; Schlenk technique; Irradiation;
Stage #2: formaldehyd In ethanol at 20℃; for 16h;
Stage #3: hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 2h; Cooling with liquid nitrogen;
A 96%
B 75%
boron trichloride
10294-34-5

boron trichloride

tributyl(cyclohex-2-en-1-yl)stannane
112520-99-7, 1177092-71-5

tributyl(cyclohex-2-en-1-yl)stannane

propionaldehyde
123-38-6

propionaldehyde

A

boron oxychloride
23361-55-9

boron oxychloride

B

C2H5CHClCHCHCH(CH2)2CH2

C2H5CHClCHCHCH(CH2)2CH2

C

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In dichloromethane (N2); addn. of Sn-compd. to mixt. of 1 equiv. EtCHO and 1 equiv. BCl3 in CH2Cl2 at -78°C, warming to room temperature; various product ratio for various conditions; treatment with sat. aq. NH4Cl;A n/a
B 95%
C n/a
(C4H9)3SnOCH(CH2Cl)2
35952-61-5

(C4H9)3SnOCH(CH2Cl)2

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

chloroacetone
78-95-5

chloroacetone

C

epichlorohydrin
106-89-8

epichlorohydrin

Conditions
ConditionsYield
63% decompn. at 210°C (1 h);A n/a
B 5%
C 95%
chloro(methyl)phenylsilane
1631-82-9

chloro(methyl)phenylsilane

tributyltin ethoxide
682-00-8

tributyltin ethoxide

A

diethoxy-methyl-phenyl-silane
775-56-4

diethoxy-methyl-phenyl-silane

B

tributyltin chloride
1461-22-9

tributyltin chloride

C

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

Conditions
ConditionsYield
2:1; room temp.;A 94%
B n/a
C n/a
2:1; room temp.;A 94%
B n/a
C n/a
Iodine monochloride
7790-99-0

Iodine monochloride

tributyltin ethoxide
682-00-8

tributyltin ethoxide

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In tetrachloromethane Ar-atmosphere; dropwise addn. of ICl to equimolar amt. of Sn-compd., stirring for 5 min; solvent removal, distn. (108-111°C, 20 mm Hg);93%
germaniumtetrachloride
10038-98-9

germaniumtetrachloride

tributyltin ethoxide
682-00-8

tributyltin ethoxide

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

tetraethoxygermanium
14165-55-0

tetraethoxygermanium

Conditions
ConditionsYield
100°C; 5 h;A n/a
B 93%
bis(cyclopentadienyl)titanium dichloride
1271-19-8

bis(cyclopentadienyl)titanium dichloride

tributyltin isocyanate
681-99-2

tributyltin isocyanate

A

bis(η-cyclopentadienyl)diisocyanato-titanium(IV)

bis(η-cyclopentadienyl)diisocyanato-titanium(IV)

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In tolueneA 78.5%
B 93%
In toluene molar ratio Ti-complex/Bu3SnNCO=1:2, evacuated sealed ampul (120-150°C, 10 h);A 78.5%
B 93%
(C4H9)3SnOCH(CH3)CH2CH2CH2Cl
41968-76-7

(C4H9)3SnOCH(CH3)CH2CH2CH2Cl

A

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
decompn. of the crude compound at 120°C (0.5 h);A 93%
B n/a
decompn. of the crude compound at 120°C (0.5 h);A 93%
B n/a
hydrogenchloride
7647-01-0

hydrogenchloride

phosphorus

phosphorus

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

A

phosphonic Acid
13598-36-2

phosphonic Acid

B

tributyltin chloride
1461-22-9

tributyltin chloride

C

hypophosphorous acid
6303-21-5

hypophosphorous acid

Conditions
ConditionsYield
Stage #1: phosphorus; tri-n-butyl-tin hydride In toluene at 20℃; for 16h; Irradiation; Schlenk technique;
Stage #2: dihydrogen peroxide In water; toluene at 20℃; for 0.5h; Cooling with liquid nitrogen;
Stage #3: hydrogenchloride In 1,4-dioxane; hexane; water; acetonitrile for 1h;
A n/a
B 93%
C n/a
tributyl(trichloroacetoxy)stannane
4342-33-0

tributyl(trichloroacetoxy)stannane

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

A

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
5307-99-3

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

B

tributyltin chloride
1461-22-9

tributyltin chloride

C

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With triphenylphosphineA 30%
B 90%
C 92%
With P(C6H5)3A 30%
B 90%
C 92%
2,5-diiodothiophene
625-88-7

2,5-diiodothiophene

trans-dichlorobis(tributylphosphine)palladium(II)
14977-08-3

trans-dichlorobis(tributylphosphine)palladium(II)

tributylethynyltin
994-89-8

tributylethynyltin

A

poly(2,5-bis(ethynyl)thiophenebis(tributylphosphine)palladium)

poly(2,5-bis(ethynyl)thiophenebis(tributylphosphine)palladium)

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
With lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran mixt. of diiodothiophene and Bu3SnC2H was stirred overnight at 70°C, NMR monitoring, after cooling to -20°C soln. of LDA was added, mixt. warmed to room temp., Pd complex was added, refluxing for 24 h; mixt. was cooled, filtered, filtrate was evapd., MeOH was added, solid was pptd., collected, washed with MeOH, dried in vac., chromd.;A 76%
B 92%
butyl magnesium bromide
693-04-9

butyl magnesium bromide

tin(IV) chloride
7646-78-8

tin(IV) chloride

A

dibutyltin chloride
683-18-1

dibutyltin chloride

B

tributyltin chloride
1461-22-9

tributyltin chloride

C

tetra-n-butyltin(IV)
1461-25-2

tetra-n-butyltin(IV)

Conditions
ConditionsYield
In diethyl etherA 0.2%
B 3.5%
C 91%
bis(cyclopentadienyl)titanium dichloride
1271-19-8

bis(cyclopentadienyl)titanium dichloride

(N-tributylstannyl)benzenesulfonamide

(N-tributylstannyl)benzenesulfonamide

A

(η(5)-cyclopentadienyltitanio)benzenesulfonamide
206437-62-9

(η(5)-cyclopentadienyltitanio)benzenesulfonamide

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In toluene byproducts: cyclopentadiene, benzenesulfonamide; 100°C, 48 h; elem. anal.;A 91%
B 65%
tributyltin fluoride
1983-10-4

tributyltin fluoride

ammonium chloride
12125-02-9

ammonium chloride

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; for 1.5h;91%
tributyltin methoxide
1067-52-3

tributyltin methoxide

acetyl chloride
75-36-5

acetyl chloride

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
90%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

tributyltin methoxide
1067-52-3

tributyltin methoxide

A

triethylmethoxysilane
2117-34-2

triethylmethoxysilane

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
A 90%
B n/a
tributyltin methoxide
1067-52-3

tributyltin methoxide

benzoyl chloride
98-88-4

benzoyl chloride

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
90%
hydrogenchloride
7647-01-0

hydrogenchloride

bis(tributylstannyl)titanium tert-butoxide

bis(tributylstannyl)titanium tert-butoxide

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
In toluene byproducts: ((C4H9)3Sn)2; toluene satd. with HCl added to Ti-compound in toluene, held for 5h at 20°C; toluene evapd. in vac., residue distd.;90%
(C4H9)3SnOC(CH3)2CH2CH2CH2Cl
41968-77-8

(C4H9)3SnOC(CH3)2CH2CH2CH2Cl

A

2,2-dimethyltetrahydrofuran
1003-17-4

2,2-dimethyltetrahydrofuran

B

tributyltin chloride
1461-22-9

tributyltin chloride

Conditions
ConditionsYield
decompn. of the crude compound at 100°C (0.5 h);A 90%
B n/a
decompn. of the crude compound at 100°C (0.5 h);A 90%
B n/a
tetra-n-butyltin(IV)
1461-25-2

tetra-n-butyltin(IV)

germaniumtetrachloride
10038-98-9

germaniumtetrachloride

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

n-butyltrichlorogermane
4872-26-8

n-butyltrichlorogermane

Conditions
ConditionsYield
other Radiation; 170°C, γ-radiation, molar ratio of educts = 1:1;A 90%
B 51%
210°C, equimolar amounts of educts;
aluminium trichloride 210°C, equimolar amounts of educts;
tributyltin butoxide
3882-70-0

tributyltin butoxide

A

tributyltin chloride
1461-22-9

tributyltin chloride

B

n-Butoxy-triethyl-german
57831-57-9

n-Butoxy-triethyl-german

Conditions
ConditionsYield
With (C2H5)3GeCl by ligand exchange at 50-60-degree.C (30 min);A n/a
B 90%
3,4-bis(diethoxyphosphoryl)-thiophene
912674-14-7

3,4-bis(diethoxyphosphoryl)-thiophene

tributyltin chloride
1461-22-9

tributyltin chloride

2,5-bis(tributylstannyl)-3,4-bis(diethoxyphosphoryl)thiophene
912674-25-0

2,5-bis(tributylstannyl)-3,4-bis(diethoxyphosphoryl)thiophene

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 5h;100%
1-bromo-3-(tertbutyl)benzene
3972-64-3

1-bromo-3-(tertbutyl)benzene

tributyltin chloride
1461-22-9

tributyltin chloride

tributyl-(3-tert-butyl-phenyl)-stannane
861859-33-8

tributyl-(3-tert-butyl-phenyl)-stannane

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 20℃; for 19h;100%
Stage #1: 1-bromo-3-(tertbutyl)benzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h;
Stage #2: tributyltin chloride In tetrahydrofuran; pentane at -78 - 20℃; for 18h;
100%
Stage #1: 1-bromo-3-(tertbutyl)benzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h;
Stage #2: tributyltin chloride In tetrahydrofuran; pentane at -78 - 20℃; for 18h;
2-(but-3-yn-1-yloxy)tetrahydropyran
40365-61-5

2-(but-3-yn-1-yloxy)tetrahydropyran

tributyltin chloride
1461-22-9

tributyltin chloride

tributyl[4-(tetrahydropyran-2-yloxy)but-1-ynyl]stannane
187339-19-1

tributyl[4-(tetrahydropyran-2-yloxy)but-1-ynyl]stannane

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%
With n-butyllithium In tetrahydrofuran27%
With n-butyllithium In tetrahydrofuran27%
With n-butyllithium In tetrahydrofuran27%
2-bromo-1,3-thiazole
3034-53-5

2-bromo-1,3-thiazole

tributyltin chloride
1461-22-9

tributyltin chloride

2-(tri-n-butylstannyl)thiazole
121359-48-6

2-(tri-n-butylstannyl)thiazole

Conditions
ConditionsYield
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In hexane Inert atmosphere;
100%
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In diethyl ether; hexane at -78℃; for 1.25h; Inert atmosphere;
Stage #2: tributyltin chloride In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere;
97%
Stage #1: 2-bromo-1,3-thiazole With n-butyllithium In diethyl ether; hexane at -78℃; for 1h;
Stage #2: tributyltin chloride In diethyl ether; hexane at -78 - 20℃;
92%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

tributyltin chloride
1461-22-9

tributyltin chloride

2-tri-n-butylstannylpyridine
17997-47-6

2-tri-n-butylstannylpyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -70℃; for 0.5h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran at -70℃; for 2h;
100%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -70℃; for 0.5h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran at -70℃; for 2h;
100%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3.5h;
99%
tributyltin chloride
1461-22-9

tributyltin chloride

2-[tris(propan-2-yl)silyl]-1,3-oxazole
433332-27-5

2-[tris(propan-2-yl)silyl]-1,3-oxazole

5-(tributylstannyl)-2-(triisopropylsilyl)oxazole
869542-43-8

5-(tributylstannyl)-2-(triisopropylsilyl)oxazole

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran at -78 - 20℃; for 17h;100%
Stage #1: 2-[tris(propan-2-yl)silyl]-1,3-oxazole With tert.-butyl lithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In diethyl ether; hexane at -78 - 20℃;
87%
Stage #1: 2-[tris(propan-2-yl)silyl]-1,3-oxazole With tert.-butyl lithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In diethyl ether; hexane at -78 - 20℃; for 1h; Inert atmosphere;
87%
Stage #1: 2-[tris(propan-2-yl)silyl]-1,3-oxazole With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In diethyl ether; hexane at -78 - 20℃; for 1h; Inert atmosphere;
87%
Stage #1: 2-[tris(propan-2-yl)silyl]-1,3-oxazole With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.833333h;
Stage #2: tributyltin chloride In tetrahydrofuran; pentane at -78 - 20℃; for 16.3333h;
tributyltin chloride
1461-22-9

tributyltin chloride

cinnamyl chloride
2687-12-9

cinnamyl chloride

(E)-cinnamyl(tributyl)tin
74785-32-3

(E)-cinnamyl(tributyl)tin

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran Sonication; nitrogen atmosphere; dropwise addn. of allyl chloride to soln. of chlorotributylstannane, magnesium turnings and a piece of iodine (0°C,irradiation of ultrasound, 45 min), aq. workup; ether extn.; (1)H-NMR spectroscopy;100%
tributyltin chloride
1461-22-9

tributyltin chloride

methyl iodide
74-88-4

methyl iodide

methyltributyltin
1528-01-4

methyltributyltin

Conditions
ConditionsYield
With ammonium fluoride In methanol Electrochem. Process;100%
Stage #1: tributyltin chloride With naphthalene; lithium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;
99%
With zinc In tetrahydrofuran; water under air atm., at room temp., cosolvent media: H2O(NH4Cl)/THF/Zn, alkyliodide was added dropwise to the alkyl tin halide in solvent mixt. over 15 min, reaction time: 1 h; Zn was filtered off, aq. phase was extd. three times with n-pentane, organic phase was washed with sat. aq. NaCl and dried over MgSO4, solvent was removed, crude oil was distilled under vac.; (119Sn NMR monitoring);84%
With zinc In cyclohexane; water under air atm., at room temp., cosolvent media: H2O(NH4Cl)/cyclohexane/Zn, alkyl iodide was added dropwise to the alkyl tin halide in solvent mixt. over 15 min, reaction time: 3.0 h; Zn was filtered off, aq. phase was extd. three times with n-pentane, organic phase was washed with sat. aq. NaCl and dried over MgSO4, solvent was removed, crude oil was distilled under vac., then chromd. using n-hexane; (119Sn NMR monitoring);52%
tributyltin chloride
1461-22-9

tributyltin chloride

3,3-dimethyl-allyl chloride
503-60-6

3,3-dimethyl-allyl chloride

prenyl tributylstannane
104108-29-4

prenyl tributylstannane

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran Sonication; nitrogen atmosphere; dropwise addn. of allyl chloride to soln. of chlorotributylstannane, magnesium turnings and a piece of iodine (0°C,irradiation of ultrasound, 45 min), aq. workup; ether extn.; (1)H-NMR spectroscopy;100%
With magnesium In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Sonication;93%
With magnesium In tetrahydrofuran at 15 - 20℃; Barbier Coupling Reaction; Inert atmosphere; Sonication;92%
2,4-hexadienyl chloride
34632-89-8

2,4-hexadienyl chloride

tributyltin chloride
1461-22-9

tributyltin chloride

E,E-2,4-hexadienyltri-n-butyltin
84363-99-5

E,E-2,4-hexadienyltri-n-butyltin

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran Sonication; nitrogen atmosphere; dropwise addn. of allyl chloride to soln. of chlorotributylstannane, magnesium turnings and a piece of iodine (0°C,irradiation of ultrasound, 45 min), aq. workup; ether extn.; (1)H-NMR spectroscopy;100%
tributyltin chloride
1461-22-9

tributyltin chloride

mesityltellurolate lithium
92720-47-3

mesityltellurolate lithium

(2,4,6-Me3C6H2Te)Sn(n-Bu)3

(2,4,6-Me3C6H2Te)Sn(n-Bu)3

Conditions
ConditionsYield
In tetrahydrofuran under Ar;100%
thiophene
188290-36-0

thiophene

tributyltin chloride
1461-22-9

tributyltin chloride

tributyl(thien-2-yl)stannane
54663-78-4

tributyl(thien-2-yl)stannane

Conditions
ConditionsYield
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78℃;
Stage #2: tributyltin chloride In tetrahydrofuran at 20℃;
100%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -80℃; for 0.5h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran at -80 - 20℃; for 72h; Inert atmosphere;
95%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
94%
(thf)3LiSi(SiMe3)3

(thf)3LiSi(SiMe3)3

tributyltin chloride
1461-22-9

tributyltin chloride

tributyl{(trimethylsilyl)silyl}stannane(IV)
128902-32-9

tributyl{(trimethylsilyl)silyl}stannane(IV)

Conditions
ConditionsYield
In diethyl ether byproducts: LiCl; under Ar, Li-compound in diethyl ether added dropwise to stirred etheral soln. of (n-Bu)3SnCl at -78°C, stirred for 9 h, warmed to ambient temp., stirred for 12 h, volatiles removed, stirred with pentane for 1 h; filtered under Ar, pentane removed, held under dynamic vacuum for 2 days; IR, NMR;100%
phenylacetic acid
103-82-2

phenylacetic acid

tributyltin chloride
1461-22-9

tributyltin chloride

tri-n-butylstannyl phenylacetate
94763-25-4

tri-n-butylstannyl phenylacetate

Conditions
ConditionsYield
in the presence of alkali hydroxyde;100%
in the presence of alkali hydroxyde;100%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

tributyltin chloride
1461-22-9

tributyltin chloride

(n-buthylstannyl)tetrathiafulvalene
139698-09-2

(n-buthylstannyl)tetrathiafulvalene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2.5h; Stille Cross Coupling;100%
With LiC4H9 In tetrahydrofuran reaction of tetrathiafulvalene with butyllithium in THF at -78°C, addn. of tributyltin chloride, warming to room temp.; chromy. on deactivated alumina;75%
Stage #1: tetrathiafulvalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
sodium 2,4,6-trimercapto-1,3,5-triazinate nonahydrate

sodium 2,4,6-trimercapto-1,3,5-triazinate nonahydrate

tributyltin chloride
1461-22-9

tributyltin chloride

[1,3,5]triazine-2,4,6-trithione
7630-40-2

[1,3,5]triazine-2,4,6-trithione

Conditions
ConditionsYield
In methanol byproducts: NaCl; (N2); stirring a mixt. of tin compd. with excess of ligand in methanol at room temp. for 24 h; filtration, evapn.; elem. anal.;100%
2,2'-Bithiophene
492-97-7

2,2'-Bithiophene

tributyltin chloride
1461-22-9

tributyltin chloride

2-(tri-n-butyl)stannyl-5,2'-bithiophene
162717-58-0

2-(tri-n-butyl)stannyl-5,2'-bithiophene

Conditions
ConditionsYield
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere;
100%
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran at -78 - 20℃; for 22h; Time; Inert atmosphere;
91%
With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 20℃; for 27h; Inert atmosphere;90%
tributyltin chloride
1461-22-9

tributyltin chloride

[(dimethylphenylsilyl)methyl]magnesium chloride
107735-20-6

[(dimethylphenylsilyl)methyl]magnesium chloride

[(phenyldimethylsilyl)methyl]tributylstannane
181022-00-4

[(phenyldimethylsilyl)methyl]tributylstannane

Conditions
ConditionsYield
In diethyl ether (Ar); addn. of a soln. of magnesium compd. in Et2O to a soln. of tin compd. in ET2O, stirring at room temp. for 7 h; addn. of H2O, extn. with Et2O, drying (MgSO4), evapn., chromy (SiO2, hexane);100%
2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran
1720-37-2

2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran

tributyltin chloride
1461-22-9

tributyltin chloride

2-(1-tributylstannyl-6-hexynyloxy) tetrahydropyran
122280-03-9

2-(1-tributylstannyl-6-hexynyloxy) 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%
3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

tributyltin chloride
1461-22-9

tributyltin chloride

tributyl-[3-(tetrahydropyran-2-yloxy)-1-propynyl]stannane
109669-44-5

tributyl-[3-(tetrahydropyran-2-yloxy)-1-propynyl]stannane

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%
tributyltin chloride
1461-22-9

tributyltin chloride

4-(N,N-dimethylamino)-2-(tributylstannyl)pyridine
396092-84-5

4-(N,N-dimethylamino)-2-(tributylstannyl)pyridine

Conditions
ConditionsYield
With n-butyllithium; 2-(N,N-dimethylamino)ethanol In tetrahydrofuran; hexane under Ar atm. soln. n-BuLi in hexane was added to soln. 2-dimethylaminoerhanol in THF at -5°C, stirred at 0°C for 30 min, 4-dimethylaminopyridine was added, stirred at 0°C for 1 h, cooled to -78°C,soln. Bu3SnCl in THF was added; after warming to room temp. soln. was concd., residue was distilled at 0.15 mm and 170-180°C, chromy. on alumina (petroleum ether);100%
Stage #1: dmap With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at -78 - 0℃; for 1.5h; Inert atmosphere;
Stage #2: tributyltin chloride In hexane at 0℃; for 1h; Inert atmosphere;
78%
Stage #1: dmap With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at -5℃; for 1.5h; Inert atmosphere;
Stage #2: tributyltin chloride In hexane at -78 - 0℃; Inert atmosphere;
73%
1-Methyl-2-propenyl phenyl selenide
17417-82-2

1-Methyl-2-propenyl phenyl selenide

tributyltin chloride
1461-22-9

tributyltin chloride

1-phenylseleno-2-methyl-3-tri-n-butylstannyl-1-propene

1-phenylseleno-2-methyl-3-tri-n-butylstannyl-1-propene

Conditions
ConditionsYield
In tetrahydrofuran byproducts: lithium diisopropylamide; dissolving methallyl phenyl selenide (5.0 mmol) in dry THF; cooling to -78°C under N2; addn. of 1.5 M lithium diisopropylamide (5.4 mmol) in THF; stirring slurry for 30 min at -78°C; dropwise addn. of ClSn(C4H9)3 (5.9 mmol);; pouring react. mixt. into ether-pentane and H2O in a separatory funnel;extg., washing org. layer with satd. NaCl; drying (Na2SO4), removing solvent; 4:1 mixt. of E:Z-isomer obtained; no further purification;;100%
tributyltin chloride
1461-22-9

tributyltin chloride

3-hydroxymethyl-5-p-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione
67549-41-1

3-hydroxymethyl-5-p-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione

(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3
75543-28-1

(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3

Conditions
ConditionsYield
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h;100%
In acetone
tributyltin chloride
1461-22-9

tributyltin chloride

5-(4-chloro-phenoxymethyl)-3-hydroxymethyl-3H-[1,3,4]oxadiazole-2-thione
68301-04-2

5-(4-chloro-phenoxymethyl)-3-hydroxymethyl-3H-[1,3,4]oxadiazole-2-thione

(C4H9)3SnOCH2C2N2OSCH2OC6H4Cl
75543-24-7

(C4H9)3SnOCH2C2N2OSCH2OC6H4Cl

Conditions
ConditionsYield
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h;100%
In acetone
tributyltin chloride
1461-22-9

tributyltin chloride

3-hydroxymethyl-5-m-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione
67549-43-3

3-hydroxymethyl-5-m-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione

(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3
75543-27-0

(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3

Conditions
ConditionsYield
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h;100%
In acetone
tributyltin chloride
1461-22-9

tributyltin chloride

3-hydroxymethyl-5-o-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione
67549-42-2

3-hydroxymethyl-5-o-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione

(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3
75543-26-9

(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3

Conditions
ConditionsYield
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h;100%
In acetone
HOC6H3(CH3)C10H19

HOC6H3(CH3)C10H19

tributyltin chloride
1461-22-9

tributyltin chloride

Bu3SnOC6H3(Me-2)menthyl-4
26246-47-9

Bu3SnOC6H3(Me-2)menthyl-4

Conditions
ConditionsYield
With potassium hydroxide In potassium hydroxide addn. of Bu3SnCl to a mixt. of phenol and 50 % aq. KOH in ethyl-methylketone, then refluxing for 8 h;100%
With KOH In potassium hydroxide; butanone aq. KOH; addn. of Bu3SnCl to a mixt. of phenol and 50 % aq. KOH in ethyl-methylketone, then refluxing for 8 h;100%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

tributyltin chloride
1461-22-9

tributyltin chloride

1,3-bis(propargyloxymethyl)-5-<3-(N,N'-dimethylamino)propoxy>benzene
221647-99-0

1,3-bis(propargyloxymethyl)-5-<3-(N,N'-dimethylamino)propoxy>benzene

{3-[3,5-bis-(3-tributylstannanyl-prop-2-ynyloxymethyl)-phenoxy]-propyl}-dimethyl-amine
221648-00-6

{3-[3,5-bis-(3-tributylstannanyl-prop-2-ynyloxymethyl)-phenoxy]-propyl}-dimethyl-amine

Conditions
ConditionsYield
In tetrahydrofuran; hexane dropwise addn. of soln. of BuLi in hexane to soln. of propargyloxy-dimethylaminopropoxybenzene in THF (0°C), stirring (0°C, 1 h), addn. of Bu3SnCl, warming to room temp., stirring (12 h); solvent removal, dissol. in satd. aq. KF, extn. into Et2O, filtration, evapn. to oil;100%
1-(tetrahydropyranyloxy)-4-pentyn
62992-46-5

1-(tetrahydropyranyloxy)-4-pentyn

tributyltin chloride
1461-22-9

tributyltin chloride

2-(1-tributylstannyl-5-pentynyloxy) tetrahydropyran
216309-29-4

2-(1-tributylstannyl-5-pentynyloxy) 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%
Stage #1: 1-(tetrahydropyranyloxy)-4-pentyn With n-butyllithium In tetrahydrofuran at 15 - 60℃; for 1h;
Stage #2: tributyltin chloride at -60 - 120℃; for 1.5h;
Stage #3: With water; sodium hydroxide In tetrahydrofuran

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