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inquiryTETRAMETHYLTIN Chemical Properties Melting point −54 °C(lit.) Boiling point 74-75 °C(lit.) density 1.291 g/mL at 25 °C(lit.) refractive index n20/D 1.441(lit.) Fp 9 °F storage temp. 2-8°C form liq
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Conditions | Yield |
---|---|
With {(C2H5)4N}Br In acetonitrile Electrolysis; Sn-cathode, 50°C; | 100% |
With {(C2H5)4N}Br In acetonitrile Electrolysis; Sn-cathode, 50°C; | 100% |
In water; acetonitrile Electrolysis; Sn-cathode, Pt-anode, 0.25 M Et4NClO4 in MeCN/water=7:1, 25°C, 10mA/cm**(-2); gas chromy.; |
Conditions | Yield |
---|---|
In benzene molar ratio 2 : 1, room temp.; | 100% |
In benzene molar ratio 2 : 1, room temp.; | 100% |
Conditions | Yield |
---|---|
80°C; | 99% |
80°C; | 99% |
Conditions | Yield |
---|---|
In neat (no solvent) stirring under N2, helding at room temp. for 4 h; destilling Me3SnCl and Me4Sn off under reduced pressure, recrystn. from ethanol, elem. anal.; | A 96% B n/a |
Conditions | Yield |
---|---|
In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C; | 95% |
In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C; | 95% |
Conditions | Yield |
---|---|
In dichloromethane N2-atmosphere; refluxing for 72 h; evapn., addn. of hexane, collection (filtration), drying (vac.); elem. anal.; | A 95% B n/a |
Conditions | Yield |
---|---|
In neat (no solvent) stirring under N2, room temp., 6 h.; Evapn., recrystn. (ethanol). Elem. anal.; | A 93.5% B n/a |
Conditions | Yield |
---|---|
In diethyl ether | A 92% B n/a C n/a |
In diethyl ether | A 92% B n/a C n/a |
1,3-dimethyl-2-(trimethylstannyl)-2-bora-1,3-diazacyclopentane
dimethyl(1,2-bis(dimethylphosphino)ethane)palladium(II)
A
1,2,3-trimethyl-[1,3,2]diazaborolidine
C
tetramethylstannane
Conditions | Yield |
---|---|
In benzene-d6 130°C (17 h); recrystn. (toluene / pentane = 1 : 4); elem. anal.; | A 91% B 68% C 84% |
Conditions | Yield |
---|---|
In dibutyl ether | 90% |
In dibutyl ether | 90% |
In dibutyl ether | 89% |
Conditions | Yield |
---|---|
In toluene boiling; | 90% |
In toluene boiling; | 90% |
hexamethyldistannane
lithium tetramethyl alanate
tetramethylstannane
Conditions | Yield |
---|---|
20 h heating at 80°C; | 90% |
20 h heating at 80°C; | 90% |
Conditions | Yield |
---|---|
In neat (no solvent) N2 or Ar-atmosphere; heating soln. of Me3Ga and Sn-compound at 55-56°C for 6 h; evapn., recrystn. (pentane); elem. anal.; | A 88.6% B n/a |
(CH3)2Sn(CH2CH2CH2)2O
trimethyltin(IV)chloride
A
5-chloro-5-methyl-1-oxa-5-stannabicylco{3.3.0(1,5)}octane
B
tetramethylstannane
Conditions | Yield |
---|---|
In neat (no solvent) Under Ar, heating of Me2Sn(CH2CH2CH2)2NMe and Me3SnCl (1h, 120°C).; Me4Sn is removed, recrystn. from CH2Cl2/hexane, elem. anal..; | A 87% B n/a |
1,1'-bis(trichlorostannyl)ferrocene
trimethyl gallium
B
tetramethylstannane
Conditions | Yield |
---|---|
In toluene under Ar atm. Me3Ga was added to suspn. 1,1'-bis(trichlorostannyl)ferrocene in toluene and heated to 68°C; react. mixt. was cooled to room temp., supernatant soln. was decanted, residue was washed with hexane (or toluene) and driedin vac.; elem. anal.; | A 86% B n/a |
Conditions | Yield |
---|---|
In diethyl ether equivalent amts. of educts, cooling with ice, dropping SnCl4, 5 to 6 h heating; distn.; | 85% |
In diethyl ether equivalent amts. of educts, cooling with ice, dropping SnCl4, 5 to 6 h heating; distn.; | 85% |
In diethyl ether equivalent amts. of educts, cooling with ice, dropping SnCl4, 5 to 6 h heating; distn.; | 45% |
Conditions | Yield |
---|---|
85% | |
85% |
(dibutylamino)trimethylstannane
tri-tert-butylindium(III)
C
hexamethyldistannane
D
tetramethylstannane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: HNBu2, isobutane, isobutene; Irradiation (UV/VIS); inert atmosphere; equimolar amts., room light, 25°C, 3 weeks (crystn.); recrystn. (CH2Cl2); elem. anal.; further unidentified products; | A n/a B 82% C n/a D n/a |
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran; diethyl ether under N2 or Ar, dropwise addn. of MeLi in THF/Et2O to Si(SnMe3)4 in THF , stirred for 22 h; removal of volatiles, extn. (pentane), concd., cooled to -40°C, filtered, dried (four crops); | A 81.2% B n/a |
Conditions | Yield |
---|---|
With methyl magnesium iodide In dibutyl ether (N2); | 81% |
Conditions | Yield |
---|---|
In neat (no solvent) N2 or Ar-atmosphere; standing soln. of Me3Ga and Sn-compound at room temp. for 20.3 h; evapn., recrystn. (pentane); elem. anal.; | A 81% B n/a |
Conditions | Yield |
---|---|
In solid Sn-complex was heated to 60°C for 0.5 h; recrystd. from hot Et2O, dried; | A 80% B n/a |
In solid Irradiation (UV/VIS); Sn-complex was exposed to daylight simulation radiation (>360 nm) for 24 h; recrystd. from hot Et2O, dried; elem. anal.; | A 70.5% B n/a |
Conditions | Yield |
---|---|
In tetrahydrofuran treating with satd. aq. citric acid soln.; | 78% |
In 1,2-dimethoxyethane treating with satd. aq. citric acid soln.; | 78% |
In tetrahydrofuran treating with satd. aq. citric acid soln.; | 78% |
Diethylamino-trimethyl-stannan
tri-tert-butylindium(III)
C
hexamethyldistannane
D
tetramethylstannane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: HNEt2, isobutane, isobutene; Irradiation (UV/VIS); inert atmosphere; equimolar amts., room light, 25°C, 2-3 weeks; recrystn. (CH2Cl2); elem. anal.; further unidentified products; | A 12% B 78% C n/a D n/a |
2,5-bis(trimethylstannyl)-1,5-hexadiene
methyllithium
A
2-(trimethylstannyl)-1,5-hexadiene
B
bis(2-hexa-1,5-dienyl)dimethylstannane
C
1-(2-hexa-1,5-dienyl)-1-methyl-2,5-bis(methylene)stannolane
D
tetramethylstannane
Conditions | Yield |
---|---|
In tetrahydrofuran under argon, compounds were added at -78°C, stirring at this temp. for 5 min, mixt. was warmed to 25°C for 10 min and cooled to -78°C, mixt was transfered to a soln. of water in THF; solvent was removed under vacuum, resulting oil was purified by glpc, elem. anal., mass spectrum; | A 11% B 14% C 75% D n/a |
Bis(trimethylstannyl)sulfur diimide
B
tetramethylstannane
Conditions | Yield |
---|---|
With methyllithium In not given equimolar amts. of MeLi and stannylsulfurdiimide reacting under Ar, Me4Sn removing by fractional distn.; identified by elem. anal., IR and NMR spectra; | A 74.5% B 41% |
methyllithium
hexamethyldistannane
trimethylstannane
A
hydrogen
B
tetramethylstannane
Conditions | Yield |
---|---|
In diethyl ether Sn2Me6 (1.12 mmol) in Et2O treated with MeLi (1.20 mmol, 1.00 M soln. in Et2O) under Ar, stirred for 30 min at 0°C, TMTH (1.12 mmol) added via syringe, stirred for 30 min at room temp., cooled to 0°C, quenched with water; H2 collected with gas measuring device, GC analysis of org. layer; | A 74% B n/a |
trifluoroacetyl iodide
hexamethyldistannane
A
tetramethylstannane
B
trimethylstannyl iodide
C
trimethyl(trifluoromethyl)tin
Conditions | Yield |
---|---|
In not given byproducts: CO, CHF3, CF3I; for 4 h;; | A n/a B n/a C 74% |
In not given byproducts: CO, CHF3, CF3I; for 4 h;; | A n/a B n/a C 74% |
Conditions | Yield |
---|---|
In tetrachloromethane dropwise addn. of dimethylsulfoxide (15.4mmol) to refluxing suspension of (CH3)3SnN(SO2CH3) in CCl4 (50ml), formation of a clear soln:; formation of crystals after 3d, -15°C; idenification of tetramethyl tin by GC-MS coupling;; | A 74% B n/a |
Conditions | Yield |
---|---|
12h, 195°C; | 73% |
12h, 195°C; | 73% |
2-bromo-5-hydroxy-[1,4]naphthoquinone
tetramethylstannane
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0); copper(I) bromide In 1,4-dioxane for 15h; Heating; | 100% |
tetrakis(triphenylphosphine) palladium(0); copper(I) bromide In 1,4-dioxane for 15h; Heating; Yield given; |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h; Mechanism; | 100% |
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h; | 100% |
With benzoylchlorobis(triphenylphosphine)palladium(II) In chloroform at 65℃; for 24h; | 95% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; poly-γ-(diphenylphosphino)propylsiloxane palladium(0) at 65℃; for 20h; | 83% |
tetramethylstannane
(2R,3S,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2,3-epoxy-6-iodo-5-cyclohexen-1-one
(+)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methyl-1-cyclohex-5-en-1-one
Conditions | Yield |
---|---|
With copper(l) iodide; triphenyl-arsane; diethylamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 80℃; for 24h; Stille reaction; | 100% |
C24H24BrFN2O4
tetramethylstannane
ethyl (3S)-(3-benzyloxycarbonylamino-6-fluoro-8-methyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; | 100% |
Conditions | Yield |
---|---|
palladium diacetate In tetrahydrofuran at 40℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With tin(IV) chloride at -20 - 60℃; for 16h; Inert atmosphere; | 100% |
With hydrogenchloride In chloroform 4h boiling, under inflow of gaseous HCl; | 70% |
With HCl In chloroform 4h boiling, under inflow of gaseous HCl; | 70% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; | 100% |
With bis-triphenylphosphine-palladium(II) chloride In toluene at 100℃; for 24h; Inert atmosphere; |
Trichlorbutylstannan
tetramethylstannane
A
dimethyltin dichloride
B
butyl-methyl-tin dichloride
Conditions | Yield |
---|---|
2-fold excess of C4H9SnCl3, 180°C, 2h; | A n/a B 99.4% |
2-fold excess of C4H9SnCl3, 180°C, 2h; | A n/a B 99.4% |
tetramethylstannane
(Z)-methyl 4-(2-bromo-2-phenylvinyl)benzoate
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 10h; Stille reaction; | 99% |
tetramethylstannane
2-benzyl-10-methyl-1-oxo-1,2,3,10-tetrahydroazepino[3,4-b]indol-5-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 100℃; for 2h; Stille reaction; | 99% |
tetramethylstannane
5-bromopyridin-3-yl 4-methylbenzenesulfonate
5-methylpyridin-3-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 17h; | 99% |
tetramethylstannane
(2S,3S,4aR,8aR)-2,3,4a,5,6,8a-hexahydro-7-iodo-2,3-dimethoxy-2,3-dimethylbenzo[b][1,4]dioxin-6-one
Conditions | Yield |
---|---|
With copper(l) iodide; triphenyl-arsane; diethylamine; tris(dibenzylideneacetone)dipalladium chloroform complex In tetrahydrofuran at 100℃; for 24h; Stille reaction; | 99% |
Conditions | Yield |
---|---|
stirring overnight at 60°F, N2-atmosphere; distd. at 15 Torr; | 99% |
molar ratio of (CH3)4Sn:SnCl4=3:1; distn.; | |
In neat (no solvent) react. Me4Sn with SnCl4 (3:1) at 130°C for 2 h; recrystn. from hexane; |
tetramethylstannane
phenyltin trichloride
A
trimethyltin(IV)chloride
B
methylphenyltin(IV) dichloride
Conditions | Yield |
---|---|
equimolar amts. of educts, 0°C, 1.5h; | A 99% B 85% |
equimolar amts. of educts, 0°C, 1.5h; | A 99% B 85% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide byproducts: methane; under inert atmosphere; anhyd. H4SiW12O40 dissolved in anhyd. DMSO; freezed at 0°C; Me4Sn added; stirred at 50°C for 2 d; half of solvent and excess Me4Sn removed under vac. at 200°C; dissolved by heating at 50°C; kept at room temp. overnight; | 99% |
5-bromoveratralaldehyde
tetramethylstannane
3,4-dimethoxy-5-methylbenzaldehyde
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide at 100℃; for 3h; Stille coupling; Inert atmosphere; Sealed vessel; | 99% |
Conditions | Yield |
---|---|
With C31H33INPPd In N,N-dimethyl-formamide at 80℃; for 24h; Stille coupling; | 98% |
With iodophenylbis(triphenylphosphine)palladium In N,N,N,N,N,N-hexamethylphosphoric triamide at 70℃; for 0.5h; | 87% |
Conditions | Yield |
---|---|
Pd(phenylimino)acenaphthene dimethyl fumarate In N,N-dimethyl-formamide at 50℃; for 16h; | 98% |
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.333333h; Mechanism; | 85% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; poly-γ-(diphenylphosphino)propylsiloxane palladium(0) at 65℃; for 20h; Product distribution; other organic halides; also organomagnesium reagents; var. solvents and temp.; | 85% |
With aluminium trichloride In dichloromethane for 20h; Ambient temperature; | 84% |
benzylchlorobis(triphenylphosphine)pa.. In chloroform at 65℃; competition with Me3SnPh; relative reaction rates of benzoyl chloride with organotins; |
tetramethylstannane
4-iodo-3-phenyl-1H-isochromen-1-one
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium at 60℃; for 117h; | 98% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide for 3h; Stille coupling; Heating; | 98% |
tetramethylstannane
Conditions | Yield |
---|---|
With lithium chloride; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Heating; | 98% |
(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone
tetramethylstannane
(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enone
Conditions | Yield |
---|---|
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane In 1-methyl-pyrrolidin-2-one at 80℃; for 6h; Stille coupling; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With sulfur dioxide 60°C, liq. SO2; | A n/a B 97% |
With SO2 60°C, liq. SO2; | A n/a B 97% |
Conditions | Yield |
---|---|
dropping Sn(CH3)4 to BBr3 for 1 h at -50°C (vigorous react.); slow warming, then short boiling under reflux; distn.; | 97% |
tetramethylstannane
phenyltin trichloride
methylphenyltin(IV) dichloride
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: (CH3)3SnCl; (N2); cooling of PhSnCl3 in Schlenk flask to 0°C; addn. dropwise of SnMe4 with stirring; stirring for 0.5 h ((J. Org. Chem. 33 (1968) 1119); pumping under vac. at room temp. for several hs; GS-MS; | 97% |
bis(benzonitrile)palladium(II) dichloride
tetramethylstannane
Conditions | Yield |
---|---|
In dichloromethane under N2 atm. to soln. (PhCN)2PdCl2 in CH2Cl2 at -40°C Me4Sn was added and stirred at -40°C for 1 h and at -30°C for 1.5 h,soln. bisimine ligand in CH2Cl2 was added at -30°C, stirred for 30 min, warmed to room temp., 5 h; soln. was filtered and concd., hexane was added, ppt. was washed with ether and dried in vacuo overnight; | 97% |
tetramethylstannane
bis(fluorosulfonyl)amide
trimethyltin(IV) di(fluorosulfonyl)amide
Conditions | Yield |
---|---|
In dichloromethane N2 atm.; equimolar ratio, refluxing (4 h); evapn.; elem. anal.; | 97% |
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