813-19-4

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);HEXA-N-BUTYLDISTANNANE;HEXA-N-BUTYLDITIN
• CAS NO: 813-19-4
• Molecular Formula: C₂₄H₅₄Sn₂
• Molecular Weight: 580.11
• EINECS: 212-383-3
• Product Categories: Classes of Metal Compounds;Sn (Tin) Compounds;Typical Metal Compounds;organotin compound
• Mol File: 813-19-4.mol
• Article Data: 62

Chemical Properties

• Boiling Point: 197-198 °C (10 mmHg)
• Flash Point: 124°C
• Appearance: colorless to yellow/liquid
• Density: 1.148 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: Freezer (-20°C)
• Solubility: Methanol (Slightly)
• Water Solubility: Immiscible with water.
• Sensitive: Air & Moisture Sensitive
• BRN: 3605476
• CAS DataBase Reference: HEXABUTYLDITIN(CAS DataBase Reference)
• NIST Chemistry Reference: HEXABUTYLDITIN(813-19-4)
• EPA Substance Registry System: HEXABUTYLDITIN(813-19-4)

Safety Data

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61
• RIDADR: UN 2788 6.1/PG 1
• WGK Germany: 3
• F: 1-10
• TSCA: No
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 813-19-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

Hexabutylditin (CAS# 813-19-4) is a building block used to synthesize stannylation of aryl halides, or to prepare functionalized arylstannates via Pd-catalyzed cross-coupling reactions.

Purification Methods

Purify it by distilling it in a vacuum and store it in the dark. [Shirai et al. Yakugaku Zasshi 90 59 1970, Chem Abstr 72 90593 1970, Beilstein 4 I 590.]

InChI:InChI=1/6C4H9.2Sn/c6*1-3-4-2;;/h6*1,3-4H2,2H3;;/r2C12H27Sn/c2*1-4-7-10-13(11-8-5-2)12-9-6-3/h2*4-12H2,1-3H3

Synthetic route

bis(trimethylsilyl)mercury (4656-04-6) + tributyltin methoxide (1067-52-3) → Methoxytrimethylsilane (1825-61-2) + bis(tri-n-butyltin) (813-19-4) + mercury

Conditions	Yield
In benzene 25°C; 0.1 h;	A 95% B 98% C 96%

tri-n-butyl-tin hydride (688-73-3) + tributyltin tert-butoxide (2724-79-0) → bis(tri-n-butyltin) (813-19-4)

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 (111-83-1) + tri-n-butyl-tin hydride (688-73-3) + lithium diisopropyl amide (4111-54-0) → octane (111-65-9) + bis(tri-n-butyltin) (813-19-4)

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 (4656-04-6) + bis(tri-n-butyltin)oxide (56-35-9) → bis(tri-n-butyltin) (813-19-4) + Bu3SnOSiMe3 (17908-18-8)

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%

dichlorobis(acetylacetonato-O,O')titanium(IV) + tri-n-butyltin lithium (4226-01-1) → titanium(III) tris-acetylacetonate + Ti(CH3COCHCOCH3)2(Sn(CH3(CH2)3)3)2 + tri-n-butyl-tin hydride (688-73-3) + bis(tri-n-butyltin) (813-19-4)

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 (1175712-18-1, 1175712-19-2) → (R)-Phenylglycinol (56613-80-0) + bis(tri-n-butyltin) (813-19-4)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate In acetonitrile Inert atmosphere; Electrolysis;	A 96% B n/a

tri-n-butyl-tin hydride (688-73-3) + lithium diisopropyl amide (4111-54-0) → hydrogen (1333-74-0) + bis(tri-n-butyltin) (813-19-4)

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%

tri-n-butyl-tin hydride (688-73-3) → bis(tri-n-butyltin) (813-19-4)

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;

tributyltin chloride (1461-22-9) → bis(tri-n-butyltin) (813-19-4)

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%

Ti(OC(CH3)3)2(Sn(C4H9)3)2 (131551-96-7) → titanium bis(tert-butoxide) + bis(tri-n-butyltin) (813-19-4)

Conditions	Yield
In xylene starting material in soln. heated at 150°C for 6h;	A n/a B 90%

diethyl phenyl orthoformate (14444-77-0) + isopropylmagnesium chloride (1068-55-9) + tri-n-butyl-tin hydride (688-73-3) → bis(tri-n-butyltin) (813-19-4) + tetra-n-butyltin(IV) (1461-25-2) + diethoxymethyltributylstannane (79411-58-8)

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 (4226-01-1) + titanium dichloride bis(tert-butoxide) (17022-82-1) → titanium(IV) tetrabutoxide + Ti(OC(CH3)3)2(Sn(C4H9)3)2 (131551-96-7) + bis(tributylstannyl)titanium + bis(tri-n-butyltin) (813-19-4) + lithium chloride

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 (16853-85-3) + tributyltin chloride (1461-22-9) → bis(tri-n-butyltin) (813-19-4)

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%

vanadocene + tributyltin acetate (56-36-0) → {(η5-cyclopentadienyl)vanadium diacetate}2 + bis(tri-n-butyltin) (813-19-4) + cyclopenta-1,3-diene (542-92-7)

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 (4226-01-1) + chloro(tristertbutoxy)titanium (5915-86-6) → titanium(IV) tetrabutoxide + bis(tri-n-butyltin) (813-19-4)

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%

bis(trimethylsilyl)mercury (4656-04-6) + tributyltin acetate (56-36-0) → bis(tri-n-butyltin) (813-19-4)

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%

vanadocene + tributylstannyl isothiocyanate (5035-65-4) → vanadocene monoisothiocyanate + bis(tri-n-butyltin) (813-19-4)

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%

vanadocene monoisothiocyanate + tributylstannyl isothiocyanate (5035-65-4) → bis(η5-cyclopentadienyl)vanadium diisothiocyanate + bis(tri-n-butyltin) (813-19-4)

Conditions	Yield
In toluene mixt. heated in an evacuated sealed ampul at 150-180°C for 15h;	A 80% B 87%

bis(trimethylsilyl)mercury (4656-04-6) + Bu3SnOSiMe3 (17908-18-8) → Hexamethyldisiloxane (107-46-0) + bis(tri-n-butyltin) (813-19-4) + mercury

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%

bis(tri-n-butyltin)oxide (56-35-9) → bis(tri-n-butyltin) (813-19-4)

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%

vanadocene + (C4H9)3SnNHC6H4SO2NHSn(C4H9)3 (206437-65-2) → N-(η(5)-cyclopentadienylvanadio)-p-(η(5)-cyclopentadienylvanadioamino)benzenesulfonamide (206437-66-3) + bis(tri-n-butyltin) (813-19-4)

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%

bis(tri-n-butyltin)oxide (56-35-9) → bis(tri-n-butyltin) (813-19-4) + tetra-n-butyltin(IV) (1461-25-2)

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 (108-86-1) + tributyltin chloride (1461-22-9) → bis(tri-n-butyltin) (813-19-4) + tributylphenylstannane (960-16-7)

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 (5847-51-8) → tri-n-butyl-tin hydride (688-73-3) + bis(tri-n-butyltin) (813-19-4) + tetra-n-butyltin(IV) (1461-25-2)

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 (109-69-3) + tributyltin chloride (1461-22-9) → bis(tri-n-butyltin) (813-19-4) + tetra-n-butyltin(IV) (1461-25-2)

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 (111-66-0) + tri-n-butyl-tin hydride (688-73-3) → bis(tri-n-butyltin) (813-19-4) + n-octyltriethyltin (16216-27-6)

Conditions	Yield
dimeric bis(tert-butylcyclopentadienyl)(μ-methyl) yttrium In benzene (Ar); stirring (room temp., 30 min); elem. anal.;	A n/a B 74%

vanadocene + tributyltin acetate (56-36-0) → bis(tri-n-butyltin) (813-19-4)

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%

vanadocene monochloride + tributylstannyl isothiocyanate (5035-65-4) → bis(η5-cyclopentadienyl)vanadium diisothiocyanate + tributyltin chloride (1461-22-9) + bis(tri-n-butyltin) (813-19-4)

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%

vanadocene + tributylstannyl 4-(tributylstannylamino)benzenesulfonate (153627-98-6) → η(5)-cyclopentadienevanadio-p-(η(5)-cyclopentadienylvanadioamino)benzenesulfonate (206437-68-5) + bis(tri-n-butyltin) (813-19-4)

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%

tributyltin formate (5847-51-8) → bis(tri-n-butyltin) (813-19-4)

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%

m-iodobenzaldehyde (696-41-3) + bis(tri-n-butyltin) (813-19-4) → 3-(tri-n-butylstannyl)benzaldehyde

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 3.5h; Heating / reflux;	100%

succinic acid anhydride (108-30-5) + bis(tri-n-butyltin) (813-19-4) → bis(tributyltin)succinate (4644-96-6)

Conditions	Yield
In not given at 60°C;	100%

iodobenzene (591-50-4) + bis(tri-n-butyltin) (813-19-4) → tributylphenylstannane (960-16-7)

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.

bis(tri-n-butyltin) (813-19-4) + methyl iodide (74-88-4) → methyltributyltin (1528-01-4)

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.

palladium (1,1,3,3-tetramethylbutyl isocyanide)2 + bis(tri-n-butyltin) (813-19-4) → palladium (1,1,3,3-tetramethylbutyl isocyanide)2(SnBu3)2

Conditions	Yield
In benzene 20°C, 1.5 h;	99%

bromobenzene (108-86-1) + bis(tri-n-butyltin) (813-19-4) → tributylphenylstannane (960-16-7)

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%

5-bromo-1H-indole (10075-50-0) + bis(tri-n-butyltin) (813-19-4) → 5-(tributylstannyl)-1H-indole (143724-34-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 110℃; for 3h; Reagent/catalyst; Inert atmosphere;	99%

methyl propargyl alcohol (764-01-2) + bis(tri-n-butyltin) (813-19-4) → (2E)-3-methyl-3-tributylstannylprop-2-en-1-ol (121882-41-5, 124607-17-6, 850354-34-6)

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) (813-19-4) + sodium 4-acetamidobenzenesulfinate (15898-43-8) → N-(4-(tributylstannyl)phenyl)acetamide

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere;	99%

methyl 6-iodo-5-methoxy-4-oxo-4H-chromene-2-carboxylate + bis(tri-n-butyltin) (813-19-4) → methyl 5-methoxy-4-oxo-6-(tributylstannyl)-4H-chromene-2-carboxylate

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 (764-01-2) + bis(tri-n-butyltin) (813-19-4) → 3-(tributylstannyl)but-2-en-1-ol (850354-34-6, 121882-41-5, 124607-17-6)

Conditions	Yield
With n-butyllithium; copper(l) cyanide In tetrahydrofuran at -10℃; Inert atmosphere; regioselective reaction;	99%

bis(tri-n-butyltin) (813-19-4) + C15H22INO5 → C27H49NO5Sn

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 23℃;	99%

bis(tri-n-butyltin) (813-19-4) → tributyltin iodide (7342-47-4) + methyltributyltin (1528-01-4)

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 (609-73-4) + bis(tri-n-butyltin) (813-19-4) → 2-(tri-n-butylstannyl)-1-nitrobenzene (79062-30-9)

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) (813-19-4) + sodium 3-chlorobenzenesulfinate (15946-37-9) → tributyl(3-chlorophenyl)stannane (24344-58-9)

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 (109-72-8, 29786-93-4) + (+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine (72170-87-7) + bis(tri-n-butyltin) (813-19-4) → (S,S)-3-tributylstannylcyclohexanone-(S)-1-amino-2-methoxymethylpyrrolidine-hydrazone

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%

6-bromo-1H-indole (52415-29-9) + bis(tri-n-butyltin) (813-19-4) → 6-(tributylstannyl)-1H-indole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 110℃; for 3h; Reagent/catalyst; Inert atmosphere;	97%

para-bromotoluene (106-38-7) + bis(tri-n-butyltin) (813-19-4) → tributyltin bromide (1461-23-0) + tributyl(p-tolyl)stannane (31614-66-1)

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%

sodium benzenesulfonate (873-55-2) + bis(tri-n-butyltin) (813-19-4) → tributylphenylstannane (960-16-7)

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) (813-19-4) + sodium 4-methylbenzenesulfinate (824-79-3) → tributyl(p-tolyl)stannane (31614-66-1)

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 (591-50-4) + bis(tri-n-butyltin) (813-19-4) → biphenyl (92-52-4) + tributylphenylstannane (960-16-7)

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) (813-19-4) + 6-bromo-2-octyl-1H-benzo[de]isoquinoline-1,3(2H)-dione → 2-octyl-6-(tributylstannyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 96h; Reflux; Darkness; Inert atmosphere;	96%

bis(tri-n-butyltin) (813-19-4) + sodium 4-fluorobenzenesulfinate (824-80-6) → tributyl(4-fluorophenyl)stannane (17151-47-2)

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%

methyl 4-(6-iodo-5-methoxy-4-oxo-4H-chromen-2-yl)butanoate + bis(tri-n-butyltin) (813-19-4) → methyl 4-[5-methoxy-4-oxo-6-(tributylstannyl)-4H-chromen-2-yl]butanoate

Conditions	Yield
With lithium chloride; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 50℃; for 4h; Inert atmosphere;	96%

Upstream product

• 109-69-3 n-Butyl chloride 
• 1461-22-9 tributyltin chloride 
• 4808-30-4 bis(tributyltin)sulfide 
• 6031-67-0 diisobutyltin hydride 
• 892-20-6 triphenylstannane 
• 688-73-3 tri-n-butyl-tin hydride 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 4786-24-7 3,3-dimethylacrylonitrile 
• 14583-98-3 1-tributylstannanyl-propan-2-one 
• 1066-87-1 (N,N-diethylamino)tributyltin 
• 18428-85-8 3-methyl-2-(tributylstannyl)butanenitrile 
• 18428-84-7 <1-Aethoxycarbonyl-2-methylpropyl-(1)>-tributylzinn 
• 110-05-4 di-tert-butyl peroxide 
• 6714-00-7 hept-5-en-2-one 

Downstream Products

• 17151-48-3 tributyl(4-chlorophenyl)stannane 
• 780766-47-4 2-(2-(dimethylaminomethyl)benzyl)-5-(tributyltin)phenylamine 
• 937183-70-5 (E)-(5-tri-butylstannyl-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-dimethylaminophenyl)-ethylene 
• 223555-04-2 2-(3-acetoxypropyl)-5-tributylstannylanisole 
• 223555-07-5 1-(4-tributylstannylphenoxy)-3-tetrahydropyranyloxypropane 
• 223555-11-1 2-[4-(tributylstannyl)phenoxy]-(R)-1-methylethyl acetate 
• 223555-15-5 (4-tributylstannyl)phenyl acetone 
• 223555-21-3 2-[4-(tributylstannyl)phenoxy]-(S)-2-methylethyl acetate 
• 223555-23-5 [4-(3-oxobutyl)phenyl]tributylstannane 
• 223555-25-7 methyl 2-methyl-3-(4-tributylstannylphenyl)propionate 
• 223555-27-9 methyl 2,2-dimethyl-3-(4-tributylstannylphenyl)propionate 
• 223555-29-1 3-methyl-3-(4-tributylstannylphenyl)butyl acetate 
• 223555-33-7 (4-butyrylphenyl)tributylstannane 
• 153435-35-9 N-methyl-4-tributylstannylbenzeneamide 

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