Chlorotributyltin Basic information Description References Product Name: Chlorotributyltin Synonyms: TBTC;N-TRI-TERT-BUTYLTIN CHLORIDE;CHLOROTRIBUTYLSTANNANE;CHLOROTRIBUTYLTIN;CHLOROTRI-N-BUTYLTIN;tributylchlorostannane;TRIBUTYLCHLOROTIN;TRIB
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inquiryProduct Name: Tri-n-butyltin chloride Other Name: TBTC; Tri-n-butyltin choride; Tri-n-butylchlorotin CAS NO.: 1461-22-9 Molecular Formula: C12H27ClSn Purity: 96% min. Appearance:Colorless clear liquid Storage:Preserve in well-closed, light-resi
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inquiryTributyltin chloride CAS: 1461-22-9 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic inte
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inquirySuperior quality, moderate price & quick delivery. Appearance:Clear colorless to pale yellow liquid Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:1kg/bag, 1kg/drum or 25kg/drum or as per your request. Applic
Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
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inquiryProduct name: Tributyltin Chloride CAS No.:1461-22-9 Molecule Formula:C12H27ClSn Molecule Weight:325.50 Purity: 35% Package:200kg/drum Description:Light yellow transparent liquid Manufacture Standards:Enterprise Standard TESTING
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inquiryStock products, own laboratoryAppearance:colorless to light yellow liquid Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
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phosphorus pentachloride
(Benzoyloxy)tributylstannan
tributyltin chloride
Conditions | Yield |
---|---|
byproducts: C6H5COCl; | 100% |
tin
n-Butyl chloride
A
dibutyltin chloride
B
tributyltin chloride
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
tributylstannyl isothiocyanate
B
tributyltin chloride
Conditions | Yield |
---|---|
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
bis(tributylstannyl)carbodiimide
A
bis(trimethylsilyl)carbodi-imide
B
tributyltin chloride
Conditions | Yield |
---|---|
In neat (no solvent) isolation from atmosphere; heating (20 - 160°C, 1 - 2 h); distn.; | A 93.5% B 98% |
diazoacetic acid ethyl ester
tri-n-butyl-tin hydride
dichlorodiphenylgermane
A
diphenylgermane
B
tributyltin chloride
C
diphenylgermylene
D
diphenylchlorogermane
Conditions | Yield |
---|---|
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
2-methylallyltributyltin
A
2-(2-methyl-2-propenyl)-1,3,2-dioxaborolane
B
tributyltin chloride
Conditions | Yield |
---|---|
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% |
dibutylchloroborane
A
trimetylsilylketene
B
dibutylborinic acid methyl ester
C
tributyltin chloride
Conditions | Yield |
---|---|
In pentane -50°C; fractionation; | A 57% B 82% C 96% |
hydrogenchloride
formaldehyd
tri-n-butyl-tin hydride
A
tributyltin chloride
B
tetrakis(hydroxymethyl)phosphonium chloride
Conditions | Yield |
---|---|
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
tributyl(cyclohex-2-en-1-yl)stannane
propionaldehyde
A
boron oxychloride
C
tributyltin chloride
Conditions | Yield |
---|---|
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
A
tributyltin chloride
B
chloroacetone
C
epichlorohydrin
Conditions | Yield |
---|---|
63% decompn. at 210°C (1 h); | A n/a B 5% C 95% |
chloro(methyl)phenylsilane
tributyltin ethoxide
A
diethoxy-methyl-phenyl-silane
B
tributyltin chloride
C
tri-n-butyl-tin hydride
Conditions | Yield |
---|---|
2:1; room temp.; | A 94% B n/a C n/a |
2:1; room temp.; | A 94% B n/a C n/a |
Conditions | Yield |
---|---|
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
tributyltin ethoxide
A
tributyltin chloride
B
tetraethoxygermanium
Conditions | Yield |
---|---|
100°C; 5 h; | A n/a B 93% |
bis(cyclopentadienyl)titanium dichloride
tributyltin isocyanate
B
tributyltin chloride
Conditions | Yield |
---|---|
In toluene | A 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
A
2-methyltetrahydrofuran
B
tributyltin chloride
Conditions | Yield |
---|---|
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
dihydrogen peroxide
tri-n-butyl-tin hydride
A
phosphonic Acid
B
tributyltin chloride
C
hypophosphorous acid
Conditions | Yield |
---|---|
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
cyclopenta-1,3-diene
A
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
B
tributyltin chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With triphenylphosphine | A 30% B 90% C 92% |
With P(C6H5)3 | A 30% B 90% C 92% |
2,5-diiodothiophene
trans-dichlorobis(tributylphosphine)palladium(II)
tributylethynyltin
B
tributyltin chloride
Conditions | Yield |
---|---|
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
tin(IV) chloride
A
dibutyltin chloride
B
tributyltin chloride
C
tetra-n-butyltin(IV)
Conditions | Yield |
---|---|
In diethyl ether | A 0.2% B 3.5% C 91% |
bis(cyclopentadienyl)titanium dichloride
A
(η(5)-cyclopentadienyltitanio)benzenesulfonamide
B
tributyltin chloride
Conditions | Yield |
---|---|
In toluene byproducts: cyclopentadiene, benzenesulfonamide; 100°C, 48 h; elem. anal.; | A 91% B 65% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 50℃; for 1.5h; | 91% |
Conditions | Yield |
---|---|
90% |
triethylsilyl chloride
tributyltin methoxide
A
triethylmethoxysilane
B
tributyltin chloride
Conditions | Yield |
---|---|
A 90% B n/a |
Conditions | Yield |
---|---|
90% |
Conditions | Yield |
---|---|
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
A
2,2-dimethyltetrahydrofuran
B
tributyltin chloride
Conditions | Yield |
---|---|
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)
germaniumtetrachloride
A
tributyltin chloride
B
n-butyltrichlorogermane
Conditions | Yield |
---|---|
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
A
tributyltin chloride
B
n-Butoxy-triethyl-german
Conditions | Yield |
---|---|
With (C2H5)3GeCl by ligand exchange at 50-60-degree.C (30 min); | A n/a B 90% |
3,4-bis(diethoxyphosphoryl)-thiophene
tributyltin chloride
2,5-bis(tributylstannyl)-3,4-bis(diethoxyphosphoryl)thiophene
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 5h; | 100% |
1-bromo-3-(tertbutyl)benzene
tributyltin chloride
tributyl-(3-tert-butyl-phenyl)-stannane
Conditions | Yield |
---|---|
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
tributyltin chloride
tributyl[4-(tetrahydropyran-2-yloxy)but-1-ynyl]stannane
Conditions | Yield |
---|---|
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 tetrahydrofuran | 27% |
With n-butyllithium In tetrahydrofuran | 27% |
With n-butyllithium In tetrahydrofuran | 27% |
2-bromo-1,3-thiazole
tributyltin chloride
2-(tri-n-butylstannyl)thiazole
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2-[tris(propan-2-yl)silyl]-1,3-oxazole
5-(tributylstannyl)-2-(triisopropylsilyl)oxazole
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
3,3-dimethyl-allyl chloride
prenyl tributylstannane
Conditions | Yield |
---|---|
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
tributyltin chloride
E,E-2,4-hexadienyltri-n-butyltin
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar; | 100% |
Conditions | Yield |
---|---|
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% |
tributyltin chloride
tributyl{(trimethylsilyl)silyl}stannane(IV)
Conditions | Yield |
---|---|
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
tributyltin chloride
tri-n-butylstannyl phenylacetate
Conditions | Yield |
---|---|
in the presence of alkali hydroxyde; | 100% |
in the presence of alkali hydroxyde; | 100% |
tetrathiafulvalene
tributyltin chloride
(n-buthylstannyl)tetrathiafulvalene
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
tributyltin chloride
2-(tri-n-butyl)stannyl-5,2'-bithiophene
Conditions | Yield |
---|---|
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
[(dimethylphenylsilyl)methyl]magnesium chloride
[(phenyldimethylsilyl)methyl]tributylstannane
Conditions | Yield |
---|---|
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
tributyltin chloride
2-(1-tributylstannyl-6-hexynyloxy) tetrahydropyran
Conditions | Yield |
---|---|
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
tributyltin chloride
tributyl-[3-(tetrahydropyran-2-yloxy)-1-propynyl]stannane
Conditions | Yield |
---|---|
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% |
dmap
tributyltin chloride
4-(N,N-dimethylamino)-2-(tributylstannyl)pyridine
Conditions | Yield |
---|---|
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
tributyltin chloride
Conditions | Yield |
---|---|
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
3-hydroxymethyl-5-p-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione
(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3
Conditions | Yield |
---|---|
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h; | 100% |
In acetone |
tributyltin chloride
5-(4-chloro-phenoxymethyl)-3-hydroxymethyl-3H-[1,3,4]oxadiazole-2-thione
(C4H9)3SnOCH2C2N2OSCH2OC6H4Cl
Conditions | Yield |
---|---|
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h; | 100% |
In acetone |
tributyltin chloride
3-hydroxymethyl-5-m-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione
(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3
Conditions | Yield |
---|---|
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h; | 100% |
In acetone |
tributyltin chloride
3-hydroxymethyl-5-o-tolyloxymethyl-3H-[1,3,4]oxadiazole-2-thione
(C4H9)3SnOCH2C2N2OSCH2OC6H4CH3
Conditions | Yield |
---|---|
With K2CO3 In acetone 1:1:1.5 mole ratio of Bu3SnCl, alc., and K2CO3; refluxing for 9 h; | 100% |
In acetone |
Conditions | Yield |
---|---|
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
tributyltin chloride
1,3-bis(propargyloxymethyl)-5-<3-(N,N'-dimethylamino)propoxy>benzene
{3-[3,5-bis-(3-tributylstannanyl-prop-2-ynyloxymethyl)-phenoxy]-propyl}-dimethyl-amine
Conditions | Yield |
---|---|
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
tributyltin chloride
2-(1-tributylstannyl-5-pentynyloxy) tetrahydropyran
Conditions | Yield |
---|---|
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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