Tetramethyltin supplier | CasNO.594-27-4

Name
TETRAMETHYLTIN
EINECS 209-833-6
CAS No. 594-27-4
Article Data232
CAS DataBase
Density 1.291 g/mL at 25 °C(lit.)
Solubility Insoluble in water. Soluble in organic solvents
Melting Point -54 °C(lit.)
Formula C₄H₁₂Sn
Boiling Point 74.499 °C at 760 mmHg
Molecular Weight 178.849
Flash Point -12.778 °C
Transport Information UN 3384 6.1/PG 1
Appearance clear colorless liquid
Safety 26-27-28-45-60-61
Risk Codes 26/27/28-50/53
Molecular Structure
Hazard Symbols N; T+
Synonyms Tin,tetramethyl- (6CI);Tetramethylstannane;
PSA 0.00000
LogP 1.95440

Synthetic route

: 7440-31-5
tin

: 74-83-9
methyl bromide

: 594-27-4
tetramethylstannane

Conditions

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.;

: 7646-78-8
tin(IV) chloride

: Dimethylaluminium-acetylacetonat

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
In benzene molar ratio 2 : 1, room temp.;	100%
In benzene molar ratio 2 : 1, room temp.;	100%

: 1066-45-1
trimethyltin(IV)chloride

: 124-41-4
sodium methylate

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
80°C;	99%
80°C;	99%

: cis-methyl 2-trimethylstannyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate

: 1066-45-1
trimethyltin(IV)chloride

: cis-methyl 2-chlorodimethylstannyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 74-87-3
methylene chloride

: 7646-78-8
tin(IV) chloride

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C;	95%
In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C;	95%

: (C6H3(CH2NMe2)2-2,6)SnMe3

: 1066-45-1
trimethyltin(IV)chloride

A: [(C6H3(CH2NMe2)2-2,6)SnMe2](Me3SnCl2)

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: cis-methyl 2-trimethylstannylcyclohexanecarboxylate

: 1066-45-1
trimethyltin(IV)chloride

: cis-methyl 2-chlorodimethylstannylcyclohexanecarboxylate

B: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
In neat (no solvent) stirring under N2, room temp., 6 h.; Evapn., recrystn. (ethanol). Elem. anal.;	A 93.5% B n/a

...Expand

: Sn(4+)*3C6H5CH2(1-)*Cl(1-)=(C6H5CH2)3SnCl

: 917-54-4
methyllithium

A: 594-27-4
tetramethylstannane

B: 766-04-1
benzyllithium

C: lithium chloride

Conditions

Conditions	Yield
In diethyl ether	A 92% B n/a C n/a
In diethyl ether	A 92% B n/a C n/a

...Expand

: 36333-59-2
1,3-dimethyl-2-(trimethylstannyl)-2-bora-1,3-diazacyclopentane

: 15630-15-6
dimethyl(1,2-bis(dimethylphosphino)ethane)palladium(II)

A: 29173-12-4
1,2,3-trimethyl-[1,3,2]diazaborolidine

: (((CH3)2PCH2)2)Pd(Sn(CH3)3)(BN2C2H4(CH3)2)

C: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
In benzene-d6 130°C (17 h); recrystn. (toluene / pentane = 1 : 4); elem. anal.;	A 91% B 68% C 84%

...Expand

: 75-16-1
methylmagnesium bromide

: 7646-78-8
tin(IV) chloride

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
In dibutyl ether	90%
In dibutyl ether	90%
In dibutyl ether	89%

: 75-74-1
Tetramethylblei-(IV)

: 7646-78-8
tin(IV) chloride

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
In toluene boiling;	90%
In toluene boiling;	90%

: 661-69-8
hexamethyldistannane

: 14281-94-8, 32661-49-7, 32661-50-0
lithium tetramethyl alanate

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
20 h heating at 80°C;	90%
20 h heating at 80°C;	90%

: 174837-79-7
Me3Sn(N(isobutyl)2)

: 1445-79-0
trimethyl gallium

A: [Me2Ga(N(isobutyl)2)]2

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 110971-32-9
(CH3)2Sn(CH2CH2CH2)2O

: 1066-45-1
trimethyltin(IV)chloride

A: 110971-31-8
5-chloro-5-methyl-1-oxa-5-stannabicylco{3.3.0(1,5)}octane

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 220231-14-1
1,1'-bis(trichlorostannyl)ferrocene

: 1445-79-0
trimethyl gallium

A: 1,1'-bis(dimethylgallyl)ferrocene

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 917-64-6
methyl magnesium iodide

: 7646-78-8
tin(IV) chloride

: 594-27-4
tetramethylstannane

Conditions

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%

: 420-60-0
trimethyltin fluoride

: 15120-50-0
pentamethylantimony

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
	85%
	85%

: 1068-79-7
(dibutylamino)trimethylstannane

: 113088-72-5
tri-tert-butylindium(III)

A: In(C(CH3)3)3*HN((CH2)3CH3)2

B: (di-n-butylamino)di-tertbutylindane

C: 661-69-8
hexamethyldistannane

D: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 18365-38-3
Tetrakis--silan

A: (C4H8O)3LiSi(Sn(CH3)3)3

B: 594-27-4
tetramethylstannane

Conditions

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

: 7646-78-8
tin(IV) chloride

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
With methyl magnesium iodide In dibutyl ether (N2);	81%

: 1084-14-6
Me3Sn(N(cyclohexyl)2)

: 1445-79-0
trimethyl gallium

A: [Me2Ga(N(cyclohexyl)2)]2

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: Me3Sn(tropolonate)

A: [Sn(CH3)2(C7H5O2)2]

B: 594-27-4
tetramethylstannane

Conditions

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

: 676-58-4
methylmagnesium chloride

: 7646-78-8
tin(IV) chloride

: 594-27-4
tetramethylstannane

Conditions

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%

: 1068-74-2
Diethylamino-trimethyl-stannan

: 113088-72-5
tri-tert-butylindium(III)

A: In(C(CH3)3)3*HN(C2H5)2

B: (diethylamino)di-tertbutylindane

C: 661-69-8
hexamethyldistannane

D: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 90886-28-5
2,5-bis(trimethylstannyl)-1,5-hexadiene

: 917-54-4
methyllithium

A: 125405-30-3
2-(trimethylstannyl)-1,5-hexadiene

B: 134940-88-8
bis(2-hexa-1,5-dienyl)dimethylstannane

C: 134967-25-2
1-(2-hexa-1,5-dienyl)-1-methyl-2,5-bis(methylene)stannolane

D: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 50518-65-5
Bis(trimethylstannyl)sulfur diimide

A: N-lithio-N'-trimethylstannylsulfurdiimide

B: 594-27-4
tetramethylstannane

Conditions

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%

: 917-54-4
methyllithium

: 661-69-8
hexamethyldistannane

: 1631-73-8
trimethylstannane

A: 1333-74-0
hydrogen

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 354-36-9
trifluoroacetyl iodide

: 661-69-8
hexamethyldistannane

A: 594-27-4
tetramethylstannane

B: 811-73-4
trimethylstannyl iodide

C: 754-25-6
trimethyl(trifluoromethyl)tin

Conditions

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%

...Expand

: trimethyltin(IV) dimesylamide

: 67-68-5
dimethyl sulfoxide

: {(CH3)2Sn(CH3S(O)CH3)4}(2+)*2{N(SO2CH3)2}(1-)={(CH3)2Sn(CH3S(O)CH3)4}{N(SO2CH3)2}2

B: 594-27-4
tetramethylstannane

Conditions

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

...Expand

: 1-methyl-2-trimethylstannyl pyrrole

: 100-52-7
benzaldehyde

: 594-27-4
tetramethylstannane

Conditions

Conditions	Yield
12h, 195°C;	73%
12h, 195°C;	73%

: 69008-03-3
2-bromo-5-hydroxy-[1,4]naphthoquinone

: 594-27-4
tetramethylstannane

: 481-42-5
5-hydroxy-2-methyl-1,4-naphthoquinone

Conditions

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;

: 594-27-4
tetramethylstannane

: 122-04-3
4-nitro-benzoyl chloride

: 100-19-6
(4-nitrophenyl)ethanone

Conditions

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%

: 594-27-4
tetramethylstannane

: 188308-06-7
(2R,3S,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2,3-epoxy-6-iodo-5-cyclohexen-1-one

: 162809-82-7
(+)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methyl-1-cyclohex-5-en-1-one

Conditions

Conditions	Yield
With copper(l) iodide; triphenyl-arsane; diethylamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 80℃; for 24h; Stille reaction;	100%

: 1007204-86-5
C24H24BrFN2O4

: 594-27-4
tetramethylstannane

: 1007202-02-9
ethyl (3S)-(3-benzyloxycarbonylamino-6-fluoro-8-methyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃;	100%

: 4-nitrobenzenediazonium o-benzenedisulfonimide

: 594-27-4
tetramethylstannane

: 99-99-0
1-methyl-4-nitrobenzene

Conditions

Conditions	Yield
palladium diacetate In tetrahydrofuran at 40℃; for 0.5h;	100%

: 594-27-4
tetramethylstannane

: 1066-45-1
trimethyltin(IV)chloride

Conditions

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%

: N-Boc 10-bromocytisine

: 594-27-4
tetramethylstannane

: N-Boc 10-methylcytisine

Conditions

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;

: 1118-46-3
Trichlorbutylstannan

: 594-27-4
tetramethylstannane

A: 753-73-1
dimethyltin dichloride

B: 15649-24-8
butyl-methyl-tin dichloride

Conditions

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%

...Expand

: 594-27-4
tetramethylstannane

: 253684-52-5
(Z)-methyl 4-(2-bromo-2-phenylvinyl)benzoate

: methyl 4-[(E)-2-methyl-2-phenylvinyl]benzoate

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 10h; Stille reaction;	99%

: 594-27-4
tetramethylstannane

: 292150-59-5
2-benzyl-10-methyl-1-oxo-1,2,3,10-tetrahydroazepino[3,4-b]indol-5-yl trifluoromethanesulfonate

: 2-benzyl-5,10-dimethyl-1,2,3,10-tetrahydroazepino[3,4-b]indol-1-one

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 100℃; for 2h; Stille reaction;	99%

: 594-27-4
tetramethylstannane

: 458569-33-0
5-bromopyridin-3-yl 4-methylbenzenesulfonate

: 458569-34-1
5-methylpyridin-3-yl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 17h;	99%

: 594-27-4
tetramethylstannane

: 334700-48-0
(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

: (2S,3S,4aR,8aR)-2,3-Dimethoxy-2,3,7-trimethyl-2,3,4a,8a-tetrahydro-5H-benzo[1,4]dioxin-6-one

Conditions

Conditions	Yield
With copper(l) iodide; triphenyl-arsane; diethylamine; tris(dibenzylideneacetone)dipalladium chloroform complex In tetrahydrofuran at 100℃; for 24h; Stille reaction;	99%

: 594-27-4
tetramethylstannane

: 7646-78-8
tin(IV) chloride

: 1066-45-1
trimethyltin(IV)chloride

Conditions

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;

: 594-27-4
tetramethylstannane

: 1124-19-2
phenyltin trichloride

A: 1066-45-1
trimethyltin(IV)chloride

B: 15649-26-0
methylphenyltin(IV) dichloride

Conditions

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%

...Expand

: dodecatungstosilic acid

: 594-27-4
tetramethylstannane

: 67-68-5
dimethyl sulfoxide

: [α-SiW12O40][trimethyltin(DMSO)2]*2DMSO

Conditions

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%

...Expand

: 6948-30-7
5-bromoveratralaldehyde

: 594-27-4
tetramethylstannane

: 80547-80-4
3,4-dimethoxy-5-methylbenzaldehyde

Conditions

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%

: 636-98-6
p-nitrobenzene iodide

: 594-27-4
tetramethylstannane

: 99-99-0
1-methyl-4-nitrobenzene

Conditions

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%

: 594-27-4
tetramethylstannane

: 98-88-4
benzoyl chloride

: 98-86-2
acetophenone

Conditions

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;

: 594-27-4
tetramethylstannane

: 118520-78-8
4-iodo-3-phenyl-1H-isochromen-1-one

: 3-phenyl-4-methyl-1H-isochromen-1-one

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium at 60℃; for 117h;	98%

: C26H26F3NO7S2

: 594-27-4
tetramethylstannane

: C26H29NO4S

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide for 3h; Stille coupling; Heating;	98%

: trifluoromethanesulfonic acid 6,10-methano-4-iodo-8,8-dimethyl-1-(toluene-4-sulfonyl)-6,6a,9a,10-tetrahydro-1H-7,9-dioxa-1-azadicyclopenta[a,g]naphthalen-5-yl ester

: 594-27-4
tetramethylstannane

: 4,5,8,8-tetramethyl-6,10-methano-1-(toluene-4-sulfonyl)-6,6a,9a,10-tetrahydro-1H-7,9-dioxa-1-azadicyclopenta[a,g]naphthalene

Conditions

Conditions	Yield
With lithium chloride; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Heating;	98%

: 1268265-30-0
(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone

: 594-27-4
tetramethylstannane

: 1268265-21-9
(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enone

Conditions

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%

: 594-27-4
tetramethylstannane

A: 2949-92-0
methanethiosulfonic acid S-methyl ester

B: trimethyltin sulfate

Conditions

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%

: 594-27-4
tetramethylstannane

: 10294-33-4
boron tribromide

: 5158-50-9
dimethylboron bromide

Conditions

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%

: 594-27-4
tetramethylstannane

: 1124-19-2
phenyltin trichloride

: 15649-26-0
methylphenyltin(IV) dichloride

Conditions

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%

: 15617-18-2, 39958-10-6, 14220-64-5
bis(benzonitrile)palladium(II) dichloride

: 1,4-di(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabutadiene

: 594-27-4
tetramethylstannane

: [(2,6-iPrC6H3NC(Me)C(Me)N-2,6-iPrC6H3)Pd(CH3)(Cl)]

Conditions

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%

...Expand

: 594-27-4
tetramethylstannane

: 14984-73-7
bis(fluorosulfonyl)amide

: 7240-46-2
trimethyltin(IV) di(fluorosulfonyl)amide

Conditions

Conditions	Yield
In dichloromethane N2 atm.; equimolar ratio, refluxing (4 h); evapn.; elem. anal.;	97%

Tetramethyltin Consensus Reports

Reported in EPA TSCA Inventory.

Tetramethyltin Standards and Recommendations

OSHA PEL: TWA 0.1 mg(Sn)/m³ (skin)
ACGIH TLV: TWA 0.1 mg(Sn)/m³; STEL 0.2 mg(Sn)/m³ (skin).
NIOSH REL: (Organotin Compounds) TWA 0.1 mg(Sn)/m³

Tetramethyltin Analytical Methods

For occupational chemical analysis use NIOSH: Organotin Compounds 5504.

Tetramethyltin Specification

The IUPAC name of this chemical is Tetramethylstannane. With the CAS registry number 594-27-4 and EINECS registry number 209-833-6, it is also named as stannane, tetramethyl-. In addition, the molecular formula is C₄H₁₂Sn and the molecular weight is 178.85. It is a kind of clear colorless liquid and belongs to the classes of Alkyl Metals; Classes of Metal Compounds; Grignard Reagents & Alkyl Metals; Sn (Tin) Compounds; Synthetic Organic Chemistry; Typical Metal Compounds.

Physical properties about this chemical are: (1)ACD/LogP: 3.49; (2)ACD/LogD (pH 5.5): 3.49; (3)ACD/LogD (pH 7.4): 3.49; (4)ACD/BCF (pH 5.5): 262.8; (5)ACD/BCF (pH 7.4): 262.8; (6)ACD/KOC (pH 5.5): 1877.48; (7)ACD/KOC (pH 7.4): 1877.48; (8)Flash Point: °C; (9)Enthalpy of Vaporization: 30.26 kJ/mol; (10)Boiling Point: 74.5 °C at 760 mmHg; (11)Vapour Pressure: 120 mmHg at 25°C.

Preparation of Tetramethylstannane: it can be prepared by methylmagnesium iodide and tin tetrachloride, which is synthesized by reacting tin metal with chlorine gas. The equation is as follows: 4CH₃MgI + SnCl₄ → (CH₃)₄Sn + 4MgICl.

Uses of Tetramethylstannane: its liquid is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones. It can react with SnMe4 to get Me3SnCl at temperatures between 100 °C and 200 °C. The equation is as follows: SnCl₄ + 3SnMe₄ → 4 Me₃SnCl. In addition, it can react with 1-iodo-4-nitro-benzeneto give 1-methyl-4-nitro-benzene. This reaction will need reagent PhPdI(PPh₃)₂ and solvent hexamethylphosphoric acid triamide. The reaction time is 0.5 hour at reaction temperature of 70 °C. The yield is about 87%.

Tetramethylstannane can react with 1-iodo-4-nitro-benzeneto give 1-methyl-4-nitro-benzene

When you are using this chemical, please be cautious about it as the following:
This chemical is very Toxic by inhalation, in contact with skin and if swallowed. And it is very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, you should avoid release to the environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If contact it with your skin, wash it immediately with plenty of ... (to be specified by the manufacturer). Moreover, take off immediately all contaminated clothing. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). This material and/or its container must be disposed of as hazardous waste. And you can refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: C[Sn](C)(C)C
(2)InChI: InChI=1/4CH3.Sn/h4*1H3;/rC4H12Sn/c1-5(2,3)4/h1-4H3
(3)InChIKey: VXKWYPOMXBVZSJ-RMHPNCEBAE

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LCLo	inhalation	2550mg/m³/10M (2550mg/m³)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA	National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. FEB1942,
mouse	LD50	intraperitoneal	18mg/kg (18mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1245, 1986.

Product Name

TETRAMETHYLTIN

Synthetic route

Tetramethyltin Consensus Reports

Tetramethyltin Standards and Recommendations

Tetramethyltin Analytical Methods

Tetramethyltin Specification

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