Trimethyltin chloride supplier

Name
TRIMETHYLTIN CHLORIDE
EINECS 213-917-8
CAS No. 1066-45-1
Article Data269
CAS DataBase
Density 0.988 g/mL at 25 °C
Solubility Soluble in water, chloroform and organic solvents.
Melting Point 37-39 °C(lit.)
Formula C3H9 Cl Sn
Boiling Point 148
Molecular Weight 199.267
Flash Point 207 °F
Transport Information UN 3146
Appearance WHITE CRYSTALS
Safety A deadly poison by intravenous route. Experimental reproductive effects. See also TIN COMPOUNDS. When heated to decomposition it emits toxic fumes of Cl⁻.
Analytical Methods:

For occupational chemical analysis use NIOSH: Organotin Compounds 5504.
Risk Codes R26/27/28;R50/53
Molecular Structure
Hazard Symbols
Synonyms Trimethyltinchloride (6CI); Chlorotrimethylstannane; Chlorotrimethyltin; M&T Chemicals1222-45; NSC 12088; NSC 92613; Trimethylchlorostannane; Trimethylchlorotin;Trimethylstannanyl chloride; Trimethylstannyl chloride; Trimethyltinmonochloride
PSA 0.00000
LogP 2.06010

Synthetic route

: 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%

: 87293-07-0
trimethyl(dimesylamino)stannane

: 98-88-4
benzoyl chloride

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

B: 120622-90-4
N,N-bis(methanesulfonyl)benzamide

Conditions

Conditions	Yield
In dichloromethane reflux for 48 h; evapn. of solvent, pptn. of N-benzoyldimesylamine, isolation of (CH3)3SnCl from filtrate;	A 100% B n/a

...Expand

: 87293-07-0
trimethyl(dimesylamino)stannane

: 98-88-4
benzoyl chloride

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

B: 120622-90-4
N,N-bis(methanesulfonyl)benzamide

Conditions

Conditions	Yield
In dichloromethane reflux for 48 h; evapn. of solvent, pptn. of N-benzoyldimesylamine, isolation of (CH3)3SnCl from filtrate;	A 100% B n/a

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: nickel(II) chloride hexahydrate

: 1070-91-3
bis(trimethyltin) sulfide

: 1066-45-1
trimethyltin(IV)chloride

Conditions

Conditions	Yield
With triphenylphosphine In ethanol; acetone byproducts: Ni, triphenylphosphonium sulfide; dropwise addn. of an ethanolic soln. of NiCl2*6H2O to a stirred soln. of ((CH3)3Sn)2S and triphenylphosphine in acetone; refluxing;; filtration;;	100%

: 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

: germanium(II) chloride dioxane

: 186268-80-4
GeC6H10(Sn(CH3)3)2

: 1066-45-1
trimethyltin(IV)chloride

Conditions

Conditions	Yield
In benzene-d6 byproducts: germanium-contg. polymer; (Ar); stirring (20°C, 2 d);	99%

: nickel(II) chloride hexahydrate

: 1070-91-3
bis(trimethyltin) sulfide

A: nickel(II) sulfide

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

Conditions

Conditions	Yield
In water; acetone dropwise addn. of an aq. soln. of NiCl2*6H2O to a stirred soln. of ((CH3)3Sn)2S in acetone at room temp.; refluxing for 5 h;; filtration;;	A 90% B 99%

...Expand

: 13894-35-4
O,O-dimethylphosphorylsulfenyl chloride

: 762-73-2
trimethyl(allyl)stannane

A: 66498-87-1
S-allyl O,O-dimethyl phosphorothioate

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

Conditions

Conditions	Yield
In tetrachloromethane from -15 deg C to RT;	A 97% B n/a
In tetrachloromethane addn. of soln. of sulfenyl chloride to soln. of stannane in CCl4 with cooling (-15°C) and stirring, warming to room temp.; solvent removed, distilln., (1)H-NMR;	A 97% B n/a

...Expand

: 940-00-1
(4-methoxyphenyl)trimethylstannane

: 93-61-8
N-methyl-N-phenylformamide

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

B: 123-11-5
4-methoxy-benzaldehyde

Conditions

Conditions	Yield
With trichlorophosphate at 50 - 70℃; for 3h;	A n/a B 96%

...Expand

: 594-27-4
tetramethylstannane

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

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

B: 15649-31-7
butyl-dimethyl-tin chloride

Conditions

Conditions	Yield
3h, 75 to 85°C;	A 96% B 91%
3h, 75 to 85°C;	A 96% B 91%

...Expand

: 14264-16-5, 53996-95-5, 62075-39-2, 39716-73-9
bis(triphenylphosphine)nickel(II) chloride

: 1070-91-3
bis(trimethyltin) sulfide

: 1066-45-1
trimethyltin(IV)chloride

Conditions

Conditions	Yield
In ethanol byproducts: Ni, triphenylphosphonium sulfide, triphenylphosphine; a mixt. of ((CH3)3Sn)2S and ((C6H5)3P)2NiCl2 in ethanol was heated at 95-100°C for 10 h;; distn.;;	95%

: 16812-43-4
bis(trimethylstannyl)methane

: 753-73-1
dimethyltin dichloride

A: 83135-39-1
bis(chlorodimethylstannyl)methane

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

Conditions

Conditions	Yield
In neat (no solvent) heated at 60°C for 12 h; distd. (12-15 Torr), recrystd. (C6H6); elem. anal.;	A 95% B n/a

...Expand

: 83135-43-7
2,2-bis(trimethylstannyl)propane

: 753-73-1
dimethyltin dichloride

A: 83135-44-8
2,2-bis(chlorodimethylstannyl)propane

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

Conditions

Conditions	Yield
In neat (no solvent) 2,2-bis(trimethylstannyl)propane placed in flash with 2 mol of dimethyldichlorostannane, heated at 60°C overnight; stirred at 15-20 Torr, warmed at 0.01 Torr to 100°C, recrystd. (CCl4); elem. anal.;	A 95% B n/a

...Expand

: 85294-03-7
3,3-bis(trimethylstannyl)propyl ethyl sulfoxide

: 753-73-1
dimethyltin dichloride

: 91230-55-6
3,3-bis(chlorodimethylstannyl)propyl ethyl sulfoxide

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

Conditions

Conditions	Yield
In dichloromethane mixt. of the sulfoxide (6.7 mmol) and SnMe2Cl2 (13.5 mmol) in CH2Cl2 refluxed for 12 h; solvent removed (rotary evaporator); SnMe3Cl removed (0.01 torr, 60 °C); recrystn. (CCl4/hexane); elem. anal.; mol. wt. calc.: 486.6; mol. wt. found: 506.6 (isopiestic in CH2Cl2 at 22 °C);	A 95% B n/a

...Expand

: 75-77-4
chloro-trimethyl-silane

: 19097-32-6
trimethyl(trifluoro-1-propynyl)stanane

A: 6618-09-3
1,1,1-trifluoro-3-trimethylsilyl-2-propyne

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

Conditions

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide mixt. heating (80°C, 0.5 h); Si-compd. isolation (vac. distn., elem. anal., IR and NMR spectroscopy);	A 92% B n/a

...Expand

: 19429-30-2
di-tert-butyltin dichloride

: 1068-70-8
tris(trimethylstannyl)amine

A: bis(trimethylstannyl)(chloro-di-tert-butylstannyl)amine

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

Conditions

Conditions	Yield
In dichloromethane (inert atmosphere); stirring (-78°C to room temp.); removal of CH2Cl2 and trapping Me3SnCl at -78°C by applying high vacuum, NMR monitoring;	A 0% B 92%

...Expand

: 594-27-4
tetramethylstannane

: 15649-29-3
Ethylbutylzinndichlorid

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

B: 15649-32-8
n-Butyl-ethylmethyl-zinnchlorid

Conditions

Conditions	Yield
4h, 120 to 130°C;	A 91% B 76%
4h, 120 to 130°C;	A 91% B 76%

...Expand

: 1529-50-6
trimethylphenoxystannane

: 124-63-0
methanesulfonyl chloride

A: 16156-59-5
phenyl methanesulfonate

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

Conditions

Conditions	Yield
In tetrachloromethane Kinetics; Me3SnOPh refluxed for 5 h with MeSO2Cl in CCl4 / kinetics measured at 120-150°C; Me3SnCl not isolated; detected by NMR;	A 91% B n/a
In further solvent(s) Kinetics; educts dissolved in CH2Br2, sealed in glass tube, heated at 120-140°C; NMR anal.;
In dichloromethane Kinetics; educts dissolved in CH2Cl2, sealed in glass tube, heated at 130-160°C; NMR anal.;
In benzonitrile Kinetics; educts dissolved in PhCN, sealed in glass tube, heated at 120-140°C; NMR anal.;
In acetonitrile Kinetics; educts dissolved in MeCN, sealed in glass tube, heated at 100-130°C; NMR anal.;

...Expand

: 13894-35-4
O,O-dimethylphosphorylsulfenyl chloride

: 64268-27-5
p-vinylbenzyltrimethylstannane

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

B: O,O-dimethyl-S-<2--2-chloroethyl>thiophosphate

Conditions

Conditions	Yield
In diethyl ether addn. of P-compound in soln. to stirred soln. of stannane at -50-70°C; solvent removed, (CH3)3SnCl isolated, extn. with ether (5 times), solvent removed; elem. anal.;	A 91% B 87%
In chloroform addn. of P-compound in soln. to stirred soln. of stannane at -20-30°C over 0.5h; solvent removed, (CH3)3SnCl isolated, chromy. (silica gel, Rf 0.07, benzene:acetone 4:1); elem. anal.;	A 48% B 35%
In tetrachloromethane soln. of equimolar amts. of starting materials mixed at -20 and 20°C; not isolated, detd. by H-NMR;
In benzene-d6 soln. of equimolar amts. of starting materials or with stannane to sulfenyl ratio of 2:1 mixed at 10°C; not isolated, detd. by H-NMR;

...Expand

: 16035-50-0
trimethyl(trimethylstannanylethynyl)silane

A: 4526-07-2
1,4-bis(trimethylsilyl)-1,3-butadiyne

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

Conditions

Conditions	Yield
With iron(III) chloride In tetrachloromethane; toluene at 25℃; for 1.5h;	A 90% B 90%
With iron(III) chloride In tetrachloromethane; cyclohexane byproducts: FeCl2; at 25°C for 1.5 h;	A 90% B n/a

: 7647-01-0
hydrogenchloride

: 87293-07-0
trimethyl(dimesylamino)stannane

A: 5347-82-0
dimesylamine

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

Conditions

Conditions	Yield
In dichloromethane stream of HCl for 3 h, stirring for 1 h at 20°C; pptn. of dimesylamine, filtration, isolation of (CH3)3SnCl from filtrate;	A n/a B 90%

...Expand

: 7647-01-0
hydrogenchloride

: 87293-07-0
trimethyl(dimesylamino)stannane

A: 5347-82-0
dimesylamine

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

Conditions

Conditions	Yield
In dichloromethane stream of HCl for 3 h, stirring for 1 h at 20°C; pptn. of dimesylamine, filtration, isolation of (CH3)3SnCl from filtrate;	A n/a B 90%

...Expand

: 119895-84-0
SiF3SiHCl2

: 1631-73-8
trimethylstannane

A: 15195-26-3
F3SiSiH3

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

Conditions

Conditions	Yield
In neat (no solvent) Warming of starting materials (in absence of solvent, vac. line) for 30 min to room temp.; Removal of Me3SnCl by passing the mixt. through a trap cooled to -95°C (toluene), IR and NMR identification of volatile resulting compd.;	A 90% B n/a
In neat (no solvent) Condensing of 1 equiv. of Si-compd. with 2 equiv. of Me3SnH at -196°C (vac. line, no solvent). React. is obsd. via F-NMR only after warming (0°C, 30 min), while at -10°C (25 min) no react. occurs.; After 1 h at 0°C peaks due to SiF3SiH2Cl and unreacted SiF3SiHCl2 disappear and Me3SnCl is removed by passing the mixt. through a trap cooled to -95°C (toluene).;	A 90% B n/a

...Expand

: tetrachloro(η-pentamethylcyclopentadienyl)tungsten(V)

: 420-60-0
trimethyltin fluoride

A: 175477-60-8
[WF4(η5-C5Me5)]

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

Conditions

Conditions	Yield
In dichloromethane stoichiometric ratio, stirring (8 h, room temp.); evapn. (vac.), washing (n-hexane, toluene), drying (vac.); elem. anal.;	A 89.5% B n/a
In toluene stoichiometric ratio, stirring (5 d, room temp.); filtn., evapn. (vac.), washing (n-hexane), drying (vac.);	A 86% B n/a

...Expand

: 97607-44-8
1-trimethylsilyl-2-phenyl-2-trimethylstannyl-ethene

: mercury dichloride

A: 156994-84-2
1-trimethylsilyl-2-phenyl-2-chloromercuri-ethene

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

Conditions

Conditions	Yield
With potassium fluoride In tetrahydrofuran Solid HgCl2 is added to a soln. of the ethene-compd. in THF at room temp. After 20 h stirring KF is added.; After filtn. and removal of the solvent the residue is sublimed at 80°C/10-E2 torr, giving a highly viscous oil; elem. anal.;	A 89% B n/a

...Expand

: 754-34-7
1,1,1,2,2,3,3-heptafluoro-3-iodo-propane

: 34664-54-5
(3,3-dimethyl-1-butynyl)trimethylstannane

A: 6130-98-9
2,2,7,7-tetramethyl-octa-3,5-diyne

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

C: 126260-37-5
5,5,6,6,7,7,7-heptafluoro-2,2-dimethyl-3-heptyne

D: 811-73-4
trimethylstannyl iodide

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;	A 2-3 B <=2 C 88% D n/a
bis-triphenylphosphine-palladium(II) chloride In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;	A 2-3 B <=2 C 87% D n/a
bis(benzonitrile)palladium(II) dichloride In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;	A 2-3 B <=2 C 70% D n/a

...Expand

: [WCl4(η5-C5Me4Et)]

: 420-60-0
trimethyltin fluoride

A: 175477-61-9
[WF4(η5-C5Me4Et)]

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

Conditions

Conditions	Yield
In dichloromethane stoichiometric ratio, stirring (8 h, room temp.); evapn. (vac.), washing (n-hexane, toluene), drying (vac.); elem. anal.;	A 88% B n/a
In toluene stoichiometric ratio, stirring (5 d, room temp.); filtn., evapn. (vac.), washing (n-hexane), drying (vac.);	A 80% B n/a

...Expand

: 1066-45-1
trimethyltin(IV)chloride

: 7440-23-5
sodium

: 17310-99-5
4-methoxy-N,N,N-trimethylbenzenaminium iodide

: 940-00-1
(4-methoxyphenyl)trimethylstannane

Conditions

Conditions	Yield
With methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of CH3OC6H4NMe3I; irradn. with stirring for30 min, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;	100%
With para-dinitrobenzene; methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CH3OC6H4NMe3I; irradn. with stirring for 30 min, quenching by addn. of MeI inexcess; evapn. of ammonia, treatment with water, extn. with ether;	34%
With methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, then addn. of CH3OC6H4NMe3I; holding in dark for 30 min; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;	14%
With para-dinitrobenzene; methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CH3OC6H4NMe3I, holding in dark for 30 min, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;	0%

...Expand

: 91-16-7
1,2-dimethoxybenzene

: 1066-45-1
trimethyltin(IV)chloride

: 134952-94-6
(2,3-dimethoxyphenyl)trimethylstannane

Conditions

Conditions	Yield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane BuLi in hexane added to stirred soln. of veratrole and TMEDA in Et2O at 0°C, warmed to 22°C, stirred 1h, cooled to -80°C, addn. of (CH3)3SnCl in Et2O, warmed to 22°C, after 90 min H2O was added, stirred (room temp. overnight); Et2O layer washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure, distn. (Kugelrohr, 110°C, 0.04 mmHg); elem. anal.;;	100%

Yield

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane BuLi in hexane added to stirred soln. of veratrole and TMEDA in Et2O at 0°C, warmed to 22°C, stirred 1h, cooled to -80°C, addn. of (CH3)3SnCl in Et2O, warmed to 22°C, after 90 min H2O was added, stirred (room temp. overnight); Et2O layer washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure, distn. (Kugelrohr, 110°C, 0.04 mmHg); elem. anal.;;

100%

: 70600-14-5
1,5-dihydro-s-indacene

: 1066-45-1
trimethyltin(IV)chloride

: 106161-63-1
1-(trimethylstannyl)-1,5-dihydro-s-indacene

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane byproducts: LiCl; To a soln. of s-indacene in THF at -78°C n-BuLi in hexane was added, mixt. allowed to warm slowly to 5-10°C; this soln. was added to a soln. of Me3SnCl in hexane;; LiCl was filtered; solvent was removed in vac., oil was crystd. on standing; elem. anal.;;	100%

: 492-97-7
2,2'-Bithiophene

: 1066-45-1
trimethyltin(IV)chloride

: 143367-56-0
5,5'-bis(trimethylstannyl)-2,2'-bithiophene

Conditions

Conditions	Yield
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 25℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -40 - 25℃; for 3h;	100%
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; for 0.583333h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane Inert atmosphere;	93%
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; for 1h;	90%

: 1066-45-1
trimethyltin(IV)chloride

: 7440-23-5
sodium

: 17311-01-2
(4-cyanophenyl)trimethylammonium iodide

: 58666-77-6
(4-cyanophenyl)trimethylstannane

Conditions

Conditions	Yield
With methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, then addn. of CNC6H4NMe3I; holding in dark for 0.08 h; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;	100%
With methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of CNC6H4NMe3I; irradn. with stirring for 0.08 h, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;	100%
With para-dinitrobenzene; methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CNC6H4NMe3I; holding in dark for 0.08 h; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether;	35%

...Expand

: potassiumhexacyanoferrate(II) trihydrate

: 1066-45-1
trimethyltin(IV)chloride

: 1112-67-0
tetrabutyl-ammonium chloride

: .

Conditions

Conditions	Yield
In water byproducts: KCl;	100%

...Expand

: 6089-04-9
3-(tetrahydropyran-2'-yloxy)propyne

: 1066-45-1
trimethyltin(IV)chloride

: 711029-24-2
2-(1-trimethylstannyl-3-propynyloxy) tetrahydropyran

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane (Ar); soln. of n-BuLi in hexane was added dropwise to soln. of alkyne inTHF at -78°C; mixt. was stirred at -78°C for 30 min; Sn c ompd. was added; mixt. was stirred for 30 min and slowly warmed from -78°C to -30°C; extd. (ether/H2O); aq. phase washed (ether); combined org. phase dried (MgSO4); filtered; concd.;	100%

: 17715-69-4
1-Bromo-2,4-dimethoxybenzene

: 1066-45-1
trimethyltin(IV)chloride

: 134952-91-3
(2,4-dimethoxyphenyl)trimethylstannane

Conditions

Conditions	Yield
With magnesium In tetrahydrofuran aryl halide added to stirred suspn. of Mg turnings in THF (under N2), heated at reflux for 90 min, cooled to room temp., addn. of (CH3)3SnCl, stirred at room temp. for 2h;; partitioned between Et2O and H2O, aq. phase extd. with Et2O, organic phase washed with H2O, dried (MgSO4), filtered, concentrated under reduced pressure, filtered through deep pad of silica (THF/hexane (1:19)); elem. anal.;;	100%

Yield

With magnesium In tetrahydrofuran aryl halide added to stirred suspn. of Mg turnings in THF (under N2), heated at reflux for 90 min, cooled to room temp., addn. of (CH3)3SnCl, stirred at room temp. for 2h;; partitioned between Et2O and H2O, aq. phase extd. with Et2O, organic phase washed with H2O, dried (MgSO4), filtered, concentrated under reduced pressure, filtered through deep pad of silica (THF/hexane (1:19)); elem. anal.;;

100%

: 29150-63-8
benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene

: 1066-45-1
trimethyltin(IV)chloride

: 1289556-30-4
2,5,8-tris(trimethylstannyl)benzo[1,2-b:3,4-b’:5,6-b’’]trithiophene

Conditions

Conditions	Yield
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene In tetrahydrofuran; hexane at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	100%
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Schlenk technique;	94%
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Reflux;	82%
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at 0℃; Inert atmosphere;	75%

: 1066-45-1
trimethyltin(IV)chloride

: 165190-76-1
4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole

: 1025451-57-3
4,7-bis(5-(trimethylstannyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole

Conditions

Conditions	Yield
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With 2,2,6,6-tetramethylpiperidinyl-lithium Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃;	100%
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	89%
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃;	85%

: 1066-45-1
trimethyltin(IV)chloride

: 108-88-3
toluene

: 4314-94-7
benzyl(trimethyl)tin

Conditions

Conditions	Yield
Stage #1: toluene With (-)-sparteine at -78℃; Stage #2: With n-butyllithium at -78 - 20℃; for 0.5h; Stage #3: trimethyltin(IV)chloride at -78℃; for 2h;	100%

: C21H24O2S3

: 1066-45-1
trimethyltin(IV)chloride

: C24H32O2S3Sn

Conditions

Conditions	Yield
Stage #1: C21H24O2S3 With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;	100%

: 4891-44-5
2-(2-ethylhexyl)thiophen

: 1066-45-1
trimethyltin(IV)chloride

: 1429306-71-7
(5-(2-ethylhexyl)thiophen-2-yl)trimethylstannane

Conditions

Conditions	Yield
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Schlenk technique;	100%
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	86.5%
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	0.68 g

: 1693-86-3
3-hexylthiophene

: 1066-45-1
trimethyltin(IV)chloride

: 154717-22-3
(3-hexylthiophene-5-yl)trimethylstannane

Conditions

Conditions	Yield
Stage #1: 3-hexylthiophene With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; for 14h;	100%
Stage #1: 3-hexylthiophene With lithium diisopropyl amide Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃;	98%
Stage #1: 3-hexylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane for 1h; Reflux; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 2h;	92%
Stage #1: 3-hexylthiophene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 4h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	82.4%
With lithium diisopropyl amide

: 7-bromo-N,N-bis(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine

: 1066-45-1
trimethyltin(IV)chloride

: N,N-bis(4-methoxyphenyl)-4'-(trimethylstannyl)biphenyl-4-amine

Conditions

Conditions	Yield
Stage #1: 7-bromo-N,N-bis(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere;	100%

: N,N-bis(4-methoxyphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophen-6-amine

: 1066-45-1
trimethyltin(IV)chloride

: N,N-bis(4-methoxyphenyl)-4,4-dimethyl-2-(trimethylstannyl)-4H-indeno[1,2-b]thiophen-6-amine

Conditions

Conditions	Yield
Stage #1: N,N-bis(4-methoxyphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophen-6-amine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere;	100%

: 4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene

: 1066-45-1
trimethyltin(IV)chloride

: 2,6-bis(trimethylstannyl)-4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene

Conditions

Conditions	Yield
Stage #1: 4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene With n-butyllithium In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere; Glovebox; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran for 0.00277778h; Glovebox;	100%

: 4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-4H-dithieno[3,2-b:2',3'-d]pyrrole

: 1066-45-1
trimethyltin(IV)chloride

: 4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-2,6-bis(trimethylstannyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole

Conditions

Conditions	Yield
Stage #1: 4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-4H-dithieno[3,2-b:2',3'-d]pyrrole With n-butyllithium In tetrahydrofuran at -78 - 5℃; for 3h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃; for 5h;	100%

: 1329426-09-6
2-(3,4,5-tris(dodecyloxy)phenyl)thiophene

: 1066-45-1
trimethyltin(IV)chloride

: 1329426-11-0
2-(3,4,5-tridodecyloxyphenyl)-5-trimethylstannylthiophene

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -40℃;	100%

: 2-hexylthieno[3,2-b]thiophene

: 1066-45-1
trimethyltin(IV)chloride

: 1595320-51-6
5′-hexyl-2,2′-bithiophene-5-trimethylstannane

Conditions

Conditions	Yield
Stage #1: 2-hexylthieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃;	100%

: 2-bromo-5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophene

: 1066-45-1
trimethyltin(IV)chloride

: (5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophen-2-yl)trimethylstannane

Conditions

Conditions	Yield
Stage #1: 2-bromo-5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane	100%

: 773093-00-8
2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane

: 1066-45-1
trimethyltin(IV)chloride

: C14H18O2S2Sn

Conditions

Conditions	Yield
Stage #1: 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane With n-butyllithium In tetrahydrofuran; water at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; water at -78 - 20℃; Inert atmosphere;	99.9%
Stage #1: 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	99.8%

: 1271438-65-3
2-(2'-butyl-1'-octyl)thiophene

: 1066-45-1
trimethyltin(IV)chloride

: 1362165-84-1
2-(2-butyloctyl)-5-trimethylstannylthiophen

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran	99.2%

: 1066-45-1
trimethyltin(IV)chloride

: 73893-87-5
(S)-2-(2-Methylbutyl)thiophene

: 1362166-27-5
(S)-2-(2-methylbutyl)-5-trimethylstannylthiophene

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran	99.1%

: 1066-45-1
trimethyltin(IV)chloride

: 226085-20-7
1-tert-butyldimethylsilyl-3-trimethylstannyl-7-azaindole

Conditions

Conditions	Yield
Stage #1: 3-bromo-1-(tert-butyldimethylsilyl)-1H-pyrrolo[2,3-b]pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -90℃; for 0.0833333h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; pentane at -90℃; for 1h;	99%

Trimethyltin chloride Chemical Properties

IUPAC Name:chloro(trimethyl)stannane
Molecular Formula:C₃H₉ClSn
Molecular Weight:199.26
EINECS:213-917-8
Density:0.988 g/mL at 25 °C
Melting Point:37-39 °C(lit.)
Boiling Point:148 °C
Flash Point:207 °F
Storage temp.:Poison room
Sensitive:Moisture Sensitive
Chlorotrimethylstannane's(1066-45-1) Synonyms: CHLOROTRIMETHYLSTANNANE;CHLOROTRIMETHYLTIN;TIN TRIMETHYL CHLORIDE;TRIMETHYLCHLOROTIN;TRIMETHYLTIN(IV) CHLORIDE;TRIMETHYLTIN CHLORIDE;(CH3)3SnCl;ai3-28454
Chlorotrimethylstannane's(1066-45-1) Molecular Structure:

Trimethyltin chloride Toxicity Data With Reference

1.	dni-rbt:oth 10 µg/L	JTEHD6 Journal of Toxicology and Environmental Health. 16 (1985),229.
2.	orl-rat LD50:12,600 µg/kg	AJPAA4 American Journal of Pathology. 97 (1979),59.
3.	ipr-rat LD50:7450 µg/kg	NETOD7 Neurobehavioral Toxicology. 4 (1982),127.
4.	ivn-mus LD50:1800 µg/kg	CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02983 .

Trimethyltin chloride Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

Trimethyltin chloride Safety Profile

A deadly poison by intravenous route. Experimental reproductive effects. See also TIN COMPOUNDS. When heated to decomposition it emits toxic fumes of Cl⁻.

Safety Information of Chlorotrimethylstannane(1066-45-1)
Hazard Codes T+,N,F
Risk Statements 26/27/28-50/53-51/53-36/37-19-11-34-40
Safety Statements 28-36/37-45-61-27-26-16-60
RIDADR UN 3146 6.1/PG 2
WGK Germany 3
RTECS WH6850000
F 10-21
TSCA Yes
HazardClass 6.1
PackingGroup II

Trimethyltin chloride 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

Trimethyltin chloride Analytical Methods

For occupational chemical analysis use NIOSH: Organotin Compounds 5504.

Product Name

TRIMETHYLTIN CHLORIDE

Synthetic route

Trimethyltin chloride Chemical Properties

Trimethyltin chloride Toxicity Data With Reference

Trimethyltin chloride Consensus Reports

Trimethyltin chloride Safety Profile

Trimethyltin chloride Standards and Recommendations

Trimethyltin chloride Analytical Methods

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