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HEXABUTYLDITIN Basic information Product Name: HEXABUTYLDITIN Synonyms: 1,1,1,2,2,2-Hexabutyl-distannane;Distannane,hexabutyl-;Hexa-n-butyldizinn;BIS(TRIBUTYLTIN);BIS[TRIBUTYLTIN(IV)];BI
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inquiryHEXABUTYLDITIN Basic information Product Name: HEXABUTYLDITIN Synonyms: 1,1,1,2,2,2-Hexabutyl-distannane;Distannane,hexabutyl-;Hexa-n-butyldizinn;BIS(TRIBUTYLTIN);BIS[TRIBUTYLTIN(IV)];BIS(TRI-N-BUTYLTIN);ditin;Hexa-n-butyL CAS: 813-19-4 MF:
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bis(trimethylsilyl)mercury
tributyltin methoxide
A
Methoxytrimethylsilane
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In benzene 25°C; 0.1 h; | A 95% B 98% C 96% |
Conditions | Yield |
---|---|
With t-C4H9OH at 110°C (200 h); | 98% |
In not given reaction for 200 h at 110°C;; | |
In not given reaction for 200 h at 110°C;; |
1-bromo-octane
tri-n-butyl-tin hydride
lithium diisopropyl amide
A
octane
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In hexane; cyclohexane to 1-bromooctane (1 mmol) and Bu3SnH (1 mmol) in hexane at 0°C added LDA (1 mmol, in cyclohexane) under Ar, stirred for 20 min, quenched; analyzed by GLPC; | A 97% B 0% |
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% |
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: LiCl, Ti(Sn(C4H9)3)1.7; addn. of Bu3SnLi to Ti-compound in soln. (-78°C), stirred, mixt. brought to 20°C, soln. became blue; evapn. in vac., residue washed with pentane, sublimation (10**-3 Torr, 90°C); elem. anal., chromy.; | A 90% B 0% C 30% D 96% |
N-[(1R)-2-hydroxy-1-phenylethyl]-N-[(1S)-1-(tributylstannyl)but-3-en-1-yl]benzenesulfonamide
A
(R)-Phenylglycinol
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate In acetonitrile Inert atmosphere; Electrolysis; | A 96% B n/a |
tri-n-butyl-tin hydride
lithium diisopropyl amide
A
hydrogen
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In diethyl ether; cyclohexane byproducts: i-Pr2NH; Bu3SnH in Et2O cooled to 0°C under Ar, LDA in cyclohexane (1.6 M) added via syringe, stirred for 60 min at room temp., hydrolysis; | A 90% B 94% |
Conditions | Yield |
---|---|
((tBuC5H4)2Y(μ-H))2 In benzene byproducts: H2; (Ar); stirring (70°C, 30 min); | 91% |
In benzene Ar-atmosphere; stirring (70°C, 0.5 h); | 91% |
[(κ2-P,N)-3-(N,N-dimethylamino)propyldiphenylphosphino]dimethylplatinum(II) In not given byproducts: H2; |
Conditions | Yield |
---|---|
In tetrahydrofuran Electrolysis; electrolysis carried out galvanostatically at 25-28°C in an atm.of dry N2, electrolyte 0.4 M LiClO4/THF; hexane added to electrolyte, ppt. filtered off, filtrate analyzed for product by GC; | 90% |
With samarium; samarium diiodide In tetrahydrofuran chlorostannane added to soln. of SmI2 in THF (cat. SmI2/Sm-mixed system); mixt. stirred for 24 h at room temp.; mixt.poured into 1.5N hydrochloric acid; extracted (diethyl ether); washed two times with aq. NaHCO3 then aq. NaCl; dried over MgSO4; filtrated; evapd.; purified by recycling HPLC wit CHCl3; | 85% |
With magnesium; samarium diiodide In tetrahydrofuran chlorostannane added to soln. of SmI2 in THF (cat. SmI2/Mg-mixed system); mixt. stirred for 24 h at room temp.;mixt. poured into 1.5N hydrocloric acid; extracted (diethyl ether); washed two times with aq. NaHCO3 then aq.NaCl; dried over MgSO4; filtrated; evapd.; purified by recycling HPLC with CHCl3; | 82% |
Conditions | Yield |
---|---|
In xylene starting material in soln. heated at 150°C for 6h; | A n/a B 90% |
diethyl phenyl orthoformate
isopropylmagnesium chloride
tri-n-butyl-tin hydride
A
bis(tri-n-butyltin)
B
tetra-n-butyltin(IV)
C
diethoxymethyltributylstannane
Conditions | Yield |
---|---|
In diethyl ether grignard reagent in Et2O adding to Sn hydride soln. in Et2O, resulting Bu3SnMgCl adding dropwise to orthoformate in Et2O, stirring for 3 h, hydrolyzing, org. phase sepg.; purified by distn. in vacuo; NMR, IR and mass spectra; | A n/a B <1 C 90% |
tri-n-butyltin lithium
titanium dichloride bis(tert-butoxide)
B
Ti(OC(CH3)3)2(Sn(C4H9)3)2
D
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane Sn-compound in THF added to Ti-compound (-78°C) in hexane, temp. raised to room temp., soln. became dark-brown; solvent evapd. in vac., residue dissolved in pentane, filtered, pentane evapd. under vac., distd.; elem. anal.; | A 80% B 0% C 37% D 75% E 90% |
lithium aluminium tetrahydride
tributyltin chloride
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
dichloro bis(acetonitrile) palladium(II) In diethyl ether; water treatment stannic chloride with LiAlH4 (Et2O, 20°C, 4 h), addn. of water, addn. of catalyst, treatment (15 min); | 89% |
dichloro bis(acetonitrile) palladium(II) In diethyl ether addn. of Bu3SnCl in ether to soln. of LiAlH4 in ether (stirring), stirring (20°C, 4 h), addn. of water, addn. of catalyst to intermediate (15 min); sepn. of org. layer (decantation), washing of residue (ether), drying of extract (over Na2SO4), removal of ether (vac.), extn. (pentane), chromy. (silica thin layer), removal of pentane, distn.; | 89% |
Conditions | Yield |
---|---|
In neat (no solvent) molar ratio Cp2V/Sn-compound 1/2, sealed ampoule, 120°C, 16 h; elem. anal.; | A 89% B 10.07% C 58.5% |
tri-n-butyltin lithium
chloro(tristertbutoxy)titanium
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In tetrahydrofuran soln. of Sn-compound added to soln. of Ti-compound at -78°C, temp. increased to 20°C, mixt. became dark-brown; solvent evapd. in vac., residue dissolved in pentane, distd.; | A 45% B 88% |
Conditions | Yield |
---|---|
In benzene byproducts: (CH3)3SiOOCH3, Hg; at 25°C, 0.5 h; | 87% |
In benzene byproducts: (CH3)3SiOOCH3, Hg; at 25°C, 0.5 h; | 87% |
Conditions | Yield |
---|---|
In hexane a mixture of the Sn compd. and the V compd. in hexane was held in an evacuated ampul for 48 h at 20°C; pptn., react. soln. contained 77% of (Sn(C4H9)3)2; elem. anal.; | A 87% B n/a |
Ar, 20°C, 48 h.; Elem. anal.; | A 87% B 77% |
Conditions | Yield |
---|---|
In toluene mixt. heated in an evacuated sealed ampul at 150-180°C for 15h; | A 80% B 87% |
bis(trimethylsilyl)mercury
Bu3SnOSiMe3
A
Hexamethyldisiloxane
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In benzene 80°C; 16 h; | A 72% B 76% C 83.5% |
In benzene 80°C; 16 h; | A 72% B 76% C 83.5% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In benzene stirring (2 h); H2O addn., extg. (CH2Cl2), drying (MgSO4), filtering, concg., distg. (vac.); | 83% |
With potassium In toluene reaction with a stoich. amt. of potassium (2 mol for 1 mol of ditin oxide); | 71% |
With titanium In tetrahydrofuran reaction with a freshly prepared titanium slurry; | 70% |
(C4H9)3SnNHC6H4SO2NHSn(C4H9)3
A
N-(η(5)-cyclopentadienylvanadio)-p-(η(5)-cyclopentadienylvanadioamino)benzenesulfonamide
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In toluene byproducts: cyclopentadiene; 120 to 130°C, 24-30 h, evacuated sealed ampule; black ppt. washing (toluene, vacuum), drying; elem. anal.; | A 74% B 82% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran a soln. of ditin oxide in dry THF was added dropwise to a suspn. of a magnesium powder, activated by BrCH2CH2Br or I2, in dry THF, mixt. was heated at reflux for 15 h; petroleum ether was added, filtered, solvents evapd., residue was distilled; | A 81% B 0% |
With sodium In neat (no solvent) stoich. amt. of sodium (2 mol for 1 mol of ditin oxide), 120°C, 48 h; unreacted Bu6Sn2O was removed by filtration in pentane through a short SiO2 column, Bu4Sn was removed by distn.; | A 71% B 1-5 |
bromobenzene
tributyltin chloride
A
bis(tri-n-butyltin)
B
tributylphenylstannane
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide In tetrahydrofuran at 35℃; for 1h; Barbier Coupling Reaction; Sonication; Inert atmosphere; | A n/a B 78% |
tributyltin formate
A
tri-n-butyl-tin hydride
B
bis(tri-n-butyltin)
C
tetra-n-butyltin(IV)
Conditions | Yield |
---|---|
heating 11.5 h at 150 to 185°C; | A 6.9% B 77.5% C 5.2% |
heating 11.5 h at 150 to 185°C; | A 6.9% B 77.5% C 5.2% |
In neat (no solvent) byproducts: CO2; heating for 11.5 h at 150-185°C under N2;; | A 6.9% B n/a C n/a |
n-Butyl chloride
tributyltin chloride
A
bis(tri-n-butyltin)
B
tetra-n-butyltin(IV)
Conditions | Yield |
---|---|
In tetrahydrofuran Electrolysis; electrolyte 0.4 M LiClO4 in THF; electrolysis carried out galvanostatically at 25-28°C in atm. of dry N2; hexane added to electrolyte, ppt. filtered off, filtrate analyzed for the products by GC; | A 20% B 76% |
oct-1-ene
tri-n-butyl-tin hydride
A
bis(tri-n-butyltin)
B
n-octyltriethyltin
Conditions | Yield |
---|---|
dimeric bis(tert-butylcyclopentadienyl)(μ-methyl) yttrium In benzene (Ar); stirring (room temp., 30 min); elem. anal.; | A n/a B 74% |
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: (C5H5V(OOCCH3)2)2, C5H5; in evacuated ampule, at 120 ° C, 16 h, without solvent; | 72% |
In neat (no solvent) byproducts: (C5H5V(OOCCH3)2)2, C5H5; in evacuated ampule, at 120 ° C, 16 h, without solvent; | 72% |
tributylstannyl isothiocyanate
B
tributyltin chloride
C
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In toluene molar ratio V-complex/Bu3SnNCS=1:2, evacuated sealed ampul (120°C, 2 h); collection (filtn.), washing (toluene), drying (vac.); elem. anal.; | A 71% B 65% C 11% |
tributylstannyl 4-(tributylstannylamino)benzenesulfonate
A
η(5)-cyclopentadienevanadio-p-(η(5)-cyclopentadienylvanadioamino)benzenesulfonate
B
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In toluene byproducts: cyclopentadiene; 160 to 170°C, 48 h, evacuated sealed ampule, double excess of V-compd.; black ppt. washing (hot THF), drying; elem. anal.; | A 70% B 60% |
Conditions | Yield |
---|---|
In hexane; N,N-dimethyl acetamide Electrolysis; hexane layer was placed for extn. of product; concn. of hexane layer in vac., column chromy. (silica gel, hexane); | 68% |
In N,N-dimethyl acetamide Electrolysis; | 68% |
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 3.5h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
In not given at 60°C; | 100% |
Conditions | Yield |
---|---|
With palladium diacetate; tricyclohexylphosphine In neat (no solvent) at 110℃; under 760.051 Torr; for 24h; Sealed tube; | 99% |
With dichloro bis(acetonitrile) palladium(II) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 2.33333h; Product distribution; other reagents, reaction time, reactants' ratio dependence; also with other R4Sn (R = Et); | 92 % Chromat. |
Conditions | Yield |
---|---|
Stage #1: bis(tri-n-butyltin) With naphthalene; lithium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 99% |
With dichloro bis(acetonitrile) palladium(II) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.0833333h; Product distribution; | 98 % Chromat. |
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
In benzene 20°C, 1.5 h; | 99% |
Conditions | Yield |
---|---|
With palladium diacetate; tricyclohexylphosphine In neat (no solvent) at 110℃; under 760.051 Torr; for 24h; Sealed tube; | 99% |
tetrakis(triphenylphosphine) palladium(0) In toluene byproducts: Bu3SnBr, PhPh; heating at 80°C with stirring under Ar atm., reaction completed when color of the soln. changed to black; solvent evapd., biaryl filtered off after recrystn., filtrate washed with aq. KF, organic layer extd. with benzene, dried over sodium sulfate, product chromd.; | 89% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 110℃; for 3h; Reagent/catalyst; Inert atmosphere; | 99% |
methyl propargyl alcohol
bis(tri-n-butyltin)
(2E)-3-methyl-3-tributylstannylprop-2-en-1-ol
Conditions | Yield |
---|---|
Stage #1: bis(tri-n-butyltin) With n-butyllithium; copper(l) cyanide In tetrahydrofuran; hexane at -78 - -40℃; for 0.583333h; Inert atmosphere; Stage #2: methyl propargyl alcohol In tetrahydrofuran; methanol; hexane at -78 - -10℃; Inert atmosphere; | 99% |
With n-butyllithium; copper(l) cyanide In tetrahydrofuran; methanol at -78 - 20℃; | 99% |
bis(tri-n-butyltin)
sodium 4-acetamidobenzenesulfinate
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere; | 99% |
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
With lithium chloride; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 50℃; for 4h; Inert atmosphere; | 99% |
methyl propargyl alcohol
bis(tri-n-butyltin)
3-(tributylstannyl)but-2-en-1-ol
Conditions | Yield |
---|---|
With n-butyllithium; copper(l) cyanide In tetrahydrofuran at -10℃; Inert atmosphere; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 23℃; | 99% |
Conditions | Yield |
---|---|
With methyl iodide; dichloro bis(acetonitrile) palladium(II) In N,N,N,N,N,N-hexamethylphosphoric triamide 20°C, molar ratio distannane/halide 1.3:1, 5 min; | A n/a B 98% |
o-nitroiodobenzene
bis(tri-n-butyltin)
2-(tri-n-butylstannyl)-1-nitrobenzene
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In toluene byproducts: (C4H9)3SnI; soln. of Bu3SnSnBu3, Pd(PPh3)4, aryl iodide in toluene heated to 80°C for 72 h under Ar; evapd., washed with aq. KF, extd. (C6H6), dried over Na2SO4, chromd. (SiO2, hexane); elem. anal.; | 98% |
With palladium diacetate; tricyclohexylphosphine In neat (no solvent) at 110℃; under 760.051 Torr; for 24h; Sealed tube; | 67% |
bis(tri-n-butyltin)
sodium 3-chlorobenzenesulfinate
tributyl(3-chlorophenyl)stannane
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere; | 98% |
n-butyllithium
(+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
With NH4Cl In tetrahydrofuran addn. of the distannane to n-BuLi in abs. THF, react. for 15 min, cooling to -100°C, warming within 3 h to -78°C, dropwise addn. of the pyrrolidine compd. and addn. of satd. NH4Cl; evapn., dissolving in Et2O, washing with H2O and satd. NaCl soln., drying (MgSO4), concn. and column chromy. (silica gel, petroleum ether-Et2O); de 42 %; | 97% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 110℃; for 3h; Reagent/catalyst; Inert atmosphere; | 97% |
para-bromotoluene
bis(tri-n-butyltin)
A
tributyltin bromide
B
tributyl(p-tolyl)stannane
Conditions | Yield |
---|---|
With palladium diacetate; tricyclohexylphosphine In neat (no solvent) at 110℃; under 760.051 Torr; for 24h; Sealed tube; | A n/a B 97% |
Conditions | Yield |
---|---|
With bis(tri-tert-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Temperature; | 97% |
With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; | 97% |
bis(tri-n-butyltin)
sodium 4-methylbenzenesulfinate
tributyl(p-tolyl)stannane
Conditions | Yield |
---|---|
With bis(tri-tert-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; | 97% |
With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere; | 97% |
iodobenzene
bis(tri-n-butyltin)
A
biphenyl
B
tributylphenylstannane
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In toluene byproducts: Bu3SnI; at 115°C for 15 h in sealed thick wall Pyrex glass ampoules; | A 3.5% B 96% |
bis(triphenylphosphine)palladium dibromide In toluene byproducts: Bu3SnI; at 115°C for 15 h in sealed thick wall Pyrex glass ampoules; | A 2% B 94% |
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene for 96h; Reflux; Darkness; Inert atmosphere; | 96% |
bis(tri-n-butyltin)
sodium 4-fluorobenzenesulfinate
tributyl(4-fluorophenyl)stannane
Conditions | Yield |
---|---|
With bis(tri-tert-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; | 96% |
With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere; | 96% |
bis(tri-n-butyltin)
Conditions | Yield |
---|---|
With lithium chloride; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 50℃; for 4h; Inert atmosphere; | 96% |
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