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inquiryBis(tributyltin) oxide Chemical Properties Melting point -45°C Boiling point 180 °C2 mm Hg(lit.) density 1.17 g/mL at 25 °C(lit.) vapor pressure <0.01 mm Hg ( 25 °C) refractive index n20/D 1.486(lit.) Fp >
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Conditions | Yield |
---|---|
In not given tin compd. was heated at 65°C under vac.; | A n/a B 100% |
Conditions | Yield |
---|---|
decompn. at 25°C within 8 h; | A 75.3% B n/a C n/a |
decompn. at 25°C within 8 h; | A 75.3% B n/a C n/a |
β-(cyclohexylthio)ethyl tri-n-butyltin sulfide
A
β-(cyclohexylthio)ethyl mercaptan
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
With silica gel In dichloromethane; pentane | A 64% B 27% |
tributylethynyltin
μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine]
A
ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 0.5h; | A 56% B n/a |
A
1-(N,N-diethylamino)cyclopentene
B
(CH3CH2CH2CH2)3SnOC5H7
C
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
byproducts: H2O, NH(C2H5)2; decompn. at 100°C for 6 h; | A 56% B 5% C n/a |
byproducts: H2O, NH(C2H5)2; decompn. at 100°C for 6 h; | A 56% B 5% C n/a |
n-butyllithium
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether under N2, Schlenk setup, 1:1 mixt., n-BuLi soln. in THF added to soln. of tin compd. in Et2O (1:1), stirred for 10 h at room temp.; water added, org. layer septd., dried (Na2SO4), evapd., elem. anal.; | 55% |
Acetonyltributylstananne
(C4H9)3SnN(C2H5)Sn(C4H9)3
A
(C4H9)3SnCH2C(CH3)N(C2H5)
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
A 40% B n/a | |
A 40% B n/a |
water
bis(tri-n-butyltin)
A
tributylphenylstannane
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar; addn. of freshly prepd. THF soln. of PhEuI to mixt. of THF and Bu3SnSnBu3, mixing at 25°C for 3 h, decompn. of react. mixt. with water acidified with HCl; thin layer chromy.; | A 25% B 23% |
tri-n-butyl-tin hydride
N,N-dimethyl-formamide
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
CpFe(CO)2(Ph3P)Me In not given heating for 48 h at 90°C; | 5% |
dicarbonyl(cyclopentadienyl)methyliron(II) In not given Irradiation (UV/VIS); for 12 h at ambient temp.; | 1% |
methyl-tricarbonyl(η-cyclopentadienyl)molybdenum In not given Irradiation (UV/VIS); for 12 h at ambient temp.; | 1% |
Conditions | Yield |
---|---|
With sodium hydroxide | |
Multi-step reaction with 2 steps 1: tetrahydrofuran 2: air View Scheme | |
Multi-step reaction with 2 steps 1: hexane View Scheme |
5-methyl-1-hexene
1-dodecyne
tributyltin chloride
9-bora-bicyclo[3.3.1]nonane
A
(Z)-2-Methyl-7-octadecen
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In not given byproducts: H2O; |
4-methylquinoline 1-oxide
tri-n-butyl-tin hydride
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In not given byproducts: H2O; |
Conditions | Yield |
---|---|
In water (CH3(CH2)3)3SnCl hydrolyzed; recrystd. from benzene; |
Na(1+)*OSn(C4H9)3(1-)=NaOSn(C4H9)3
tributyltin chloride
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In methanol; toluene byproducts: NaCl; (Ar); Schlenk tube technique; Bu3SnCl in toluene was added dropwise to NaOSn(C4H9)3 in methanol; mixt. was refluxed for 6 h; NaCl was centrifuged; solvent was removed in vac.; residue was distd. under reduced pressure; elem. anal.; |
Conditions | Yield |
---|---|
In not given byproducts: H2O; |
Conditions | Yield |
---|---|
In toluene equimolar amts.; | |
In toluene equimolar amts.; |
Conditions | Yield |
---|---|
byproducts: H2O; | |
byproducts: H2O; on melting; |
Conditions | Yield |
---|---|
In not given byproducts: CHCl3; hydrolysis;; | |
In not given byproducts: CHCl3; hydrolysis;; |
tributyl-tribromomethyl-stannane
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In not given byproducts: CHBr3; hydrolysis;; | |
In not given byproducts: CHBr3; hydrolysis;; |
Phenylsulfonylmethyl-tri-n-butylzinn
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
With air | |
With air | |
With air |
(C4H9)3SnONC(NH2)CH3
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
distn. at 180°C / 0.1 Torr; | |
distn. at 180°C / 0.1 Torr; |
Ethyl-(tributyl-stannyl)-sulfit
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
With water byproducts: C2H5OH, SO2; |
(C4H9)3SnONC(NH2)C2H5
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
distn. at 180°C / 0.1 Torr; | |
distn. at 180°C / 0.1 Torr; |
Conditions | Yield |
---|---|
With H2O byproducts: CH3COCH2CH(CH3)2; rapid hydrolysis; |
(C4H9)3SnONC(NH2)C3H7
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
distn. at 180°C / 0.1 Torr; | |
distn. at 180°C / 0.1 Torr; |
Conditions | Yield |
---|---|
With water hydrolysis; | |
With H2O hydrolysis; |
Tributylzinnester des Acetylglycins
benzylamine
A
(C6H5CH2NH3)(1+)*(CH3CONHCH2COO)(1-)
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In 1,4-dioxane; water dioxane:water=6:1, room temp., 4 h; | A >99 B n/a |
In 1,4-dioxane; water dioxane:water=6:1, room temp., 4 h; | A >99 B n/a |
Phenyl glycidyl ether
tributyl(1-chloro-3-phenoxy-2-propanyloxy)stannane
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide const. temp. (+/-1°C) in range 363-393 K in air or nitrogen atmosphere; monitoring by concn. accumulation of chloride ion (potentiometric anal.); |
N-acetyl-D,L-valine
bis(tri-n-butyltin)oxide
N-acetyl-DL-CH3CH(CH3)CHNHCOO-tri-n-butyltin
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
byproducts: H2O; | 100% |
In toluene byproducts: H2O; azeotropic dehydration with toluene; recrystn. (benzene) or sublimation; |
bis(tri-n-butyltin)oxide
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
(C4H9)3SnOCH2C7H5O5(CH3)4
Conditions | Yield |
---|---|
byproducts: H2O; dehydration of 1:2 mixt. of Bu3SnOSnBu3 and alc.; separation of water by distn. or azeotropic distn. in benzene or toluene; | 100% |
byproducts: H2O; dehydration of 1:2 mixt. of Bu3SnOSnBu3 and alc.; separation of water by distn. or azeotropic distn. in benzene or toluene; | 100% |
Conditions | Yield |
---|---|
In tetrachloromethane byproducts: (C4H9)3SnOCHO; 23 h;; | 100% |
In tetrachloromethane byproducts: (C4H9)3SnOCHO; 23 h;; | 100% |
Conditions | Yield |
---|---|
In benzene | 100% |
In benzene | 100% |
92% |
bis(tri-n-butyltin)oxide
Propiolic acid
Propiolsaeure-tri-n-butylstannylester
Conditions | Yield |
---|---|
In benzene byproducts: H2O, dicarboxylate; mole ratio of (C4H9)3SnOSn(C4H9)3 and carboxylic acid 1:2; at 20°C or at reflux temp. to remove of water formed by azeotropic distn.; | 100% |
bis(tri-n-butyltin)oxide
acetone oxime
Isopropylidenaminooxy-tributyl-stannan
Conditions | Yield |
---|---|
In toluene 1:2; azeotropic dehydration; 2 h; | 100% |
In benzene 1:2; azeotropic dehydration; 2 h; | 100% |
In benzene 1:2; azeotropic dehydration; 2 h; | 100% |
heptafluorobutyric Acid
bis(tri-n-butyltin)oxide
Tributyl-heptafluorbutyroxy-zinn
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
byproducts: H2O; | 100% |
Perfluorooctanoic acid
bis(tri-n-butyltin)oxide
Tributyl-perfluoroctanoyloxy-zinn
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
byproducts: H2O; | 100% |
2-Trifluoromethylbenzimidazole
bis(tri-n-butyltin)oxide
1-(tri-n-butylstannyl)-2-trifluoromethylbenzimidazole
Conditions | Yield |
---|---|
In benzene to a soln. of imidazole-compd. was added a soln. of Sn-compd., refluxed for 3.5 h; cooled to room temp., evapn., elem. anal.; | 100% |
3-oxo-1,4-benzothiazin-2-ylacetic acid
bis(tri-n-butyltin)oxide
Tributylzinn-dihydro-oxo-benzothiazin-acetat
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
bis(tri-n-butyltin)oxide
N,N'-di(4-hydroxybenzyl)isopthalamide
C6H4(CONHCH2C6H4OSn(C4H9)3)2
Conditions | Yield |
---|---|
In toluene byproducts: H2O; stoichiometric ratio, refluxing (20 h); cooling, evapn., drying (vac., 2 h); | 100% |
1-hydroxy-pyrrolidine-2,5-dione
bis(tri-n-butyltin)oxide
(C4H9)3SnONC4H4O2
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: H2O; heating in 2/1 ratio and gradually evacuating (50-1 mm) for 30-40 min; IR; elem.anal.; | 99.7% |
In neat (no solvent) byproducts: H2O; heating; elem. anal.; | 99.7% |
heating; | >99 |
heating; | >99 |
Conditions | Yield |
---|---|
byproducts: H2O; B(OH)3 excess; 160°C; | 99% |
byproducts: H2O; B(OH)3 excess; 160°C; | 99% |
bis(tri-n-butyltin)oxide
1,2,3-tris(tributyltinoxy) propane
Conditions | Yield |
---|---|
With glycerol In neat (no solvent) glycerol to bis(tributyltin) oxide ratio 2:3; mixed, heated at 100-150°C for 1 h at P=50 mm; evacuated to P=1 mm for 0.5 h, heated at 190-220°C; distd., IR, elem. anal.; | 99% |
Conditions | Yield |
---|---|
In toluene byproducts: H2O; mixt. of (Bu3Sn)2O and PhSH (1:2 molar ratio) refluxed (12 h) in toluenewith removal of H2O (Dean-Stark apparatus); toluene removed (vac.); residue distd. (vac.); | 99% |
In toluene byproducts: H2O; refluxing for 2 h, removing H2O with a water separator; | 80% |
N-hydroxybenzenecarboximidamide
bis(tri-n-butyltin)oxide
(C4H9)3SnONC(NH2)C6H5
Conditions | Yield |
---|---|
In benzene 1:2; azeotropic dehydration; 2 h; | 99% |
In benzene 1:2; azeotropic dehydration; 2 h; | 99% |
morpholine
maleiimide
bis(tri-n-butyltin)oxide
(C4H9)3Sn(C8H11N2O3)
Conditions | Yield |
---|---|
In methanol amine and maleimide added to soln. of trialkyltin oxide in CH3OH (molar ratio 10:2:1), refluxed for half h; evapn.; | 99% |
2,3-dibromomaleimide
bis(tri-n-butyltin)oxide
N-tributylstannyl-2,3-dibromomaleimide
Conditions | Yield |
---|---|
In not given byproducts: H2O; solvent toluene or heptane; azeotropic removal water and solvent, recrystn.; elem. anal.; | 99% |
In water; benzene to a soln. of (Bu3Sn)2O in benzene was added imide in water (molar ratio oxide/imide = 1/2); shaking at room temp. for 15-20 min, org. layer was separated, water layer washed with benzene; org. layers were combined; drying over MgSO4, evapn.; | 96% |
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In methanol at 25℃; for 24h; | 99% |
5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-hydroxymethyl-1H-imidazole
methyl isocyanate
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In tetrahydrofuran | 98% |
Conditions | Yield |
---|---|
With acetic acid byproducts: H2O; heating; | 98% |
With CH3COOH byproducts: H2O; heating; | 98% |
With acetic acid In benzene byproducts: H2O; |
bis(pinacolato)diborane
bis(tri-n-butyltin)oxide
(C4H9)3SnOBO2C2(CH3)4
Conditions | Yield |
---|---|
1:1; 130°C; distn.; | 98% |
1:1; 130°C; distn.; | 98% |
bis(tri-n-butyltin)oxide
2,2'-bis-(1,2-dihydro-4-oxo-3,1-benzoxazine)
Conditions | Yield |
---|---|
In benzene byproducts: H2O; in refluxing benzene; H2O was removed as azeotrope of benzene; elem. anal.; | 98% |
(β-carboxyethyl)diallylisocyanurate
bis(tri-n-butyltin)oxide
diallyl 2-[(tributylstannyloxy)carbonyl]ethyl isocyanurate
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: H2O; heating in 2/1 ratio and gradually evacuating (50-1 mm) for 30-40 min; IR; elem.anal.; | 98% |
In neat (no solvent) byproducts: H2O; heating; elem. anal.; | 98% |
bis(tri-n-butyltin)oxide
(C4H9)3SnOOCC6I4COOCH2CH(C6H13)C8H17-2
Conditions | Yield |
---|---|
In benzene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
In toluene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
In toluene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
In benzene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
Ethyl propionate
bis(tri-n-butyltin)oxide
3-tert-butyl-isoxazole-5-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
In toluene | 97% |
In toluene | 97% |
phosphonic acid diethyl ester
bis(tri-n-butyltin)oxide
O-ethyl-O'-tri-n-butylstannyl phosphonate
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: diethylether; (Ar); addn. of TBTO to phosphonate with stirring, heating to 10°C (4 h); concn. in vac. at 40-80°C; elem. anal.; | 97% |
In not given (Ar); excess of diethylphosphonate; (31)P-NMR spectroscopic monitoring; |
Conditions | Yield |
---|---|
by heating at 140°C for 1 h; | 97% |
by heating at 90-100°C for 1.25 h; | 97% |
by heating at 140°C for 1 h; | 97% |
by heating at 90-100°C for 1.25 h; | 97% |
bis(trimethylsilyl)mercury
bis(tri-n-butyltin)oxide
A
bis(tri-n-butyltin)
B
Bu3SnOSiMe3
Conditions | Yield |
---|---|
In hexane byproducts: Hg; 2:1; 25°C; 0.2 h; | A n/a B 97% |
In benzene byproducts: Hg; 2:1; 25°C; 0.2 h; | A n/a B 97% |
In benzene byproducts: Hg; 2:1; 25°C; 0.2 h; | A n/a B 97% |
In hexane byproducts: Hg; 2:1; 25°C; 0.2 h; | A n/a B 97% |
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