Conditions | Yield |
---|---|
In methanol refluxing under N2 for 96 h;; removal of volatiles by distn.; washing of the solid residue with etherin portions; ether extract afforded SnClPh3; elem. anal.;; | A 99% B n/a |
Conditions | Yield |
---|---|
In methanol refluxing under N2 for 48 h;; removal of volatiles by distn.; residue was washed with ether in portions; ether extract afforded SnClPh3; elem. anal.;; | A 99% B n/a |
Conditions | Yield |
---|---|
With bismuth(III) chloride 5h boiling; | 98% |
Conditions | Yield |
---|---|
Gallium trichloride | 96% |
Gallium trichloride | 96% |
In not given Kocheshkov redistribution reaction (K. A. Kocheshkov, M. M. Nadi and A. P. Aleksandrov Chem. Ber. 67 (1934) 1348; |
Conditions | Yield |
---|---|
In toluene under Ar, stirred for 30 min at room temp.; removal of solvent in vac., dissolved in benzene, addn. of pentane, filtered, filtrate concd. in vac., addn. of pentane, filtered, washed with pentane, dried in vac., recrystd. (toluene/pentane 1:10); elem. anal.; | A 96% B n/a |
Conditions | Yield |
---|---|
In toluene under Ar, stirred for 30 min at room temp.; concn. in vac., addn. of pentane, filtered, washed with toluene/pentane (1:5), filtrate brought to dryness in vac., dissolved in toluene/pentane (1:3), stored at -78°C, filtered, washed with pentane, dried in vac.; elem. anal.; | A 95% B n/a |
Conditions | Yield |
---|---|
In toluene under Ar, stirred for 30 min at room temp.; removal of solvent in vac., dissolved in benzene, addn. of pentane, filtered, filtrate concd. in vac., addn. of pentane, filtered, washed with pentane, dried in vac., recrystd. (toluene/pentane 1:10); elem. anal.; | A 74% B n/a |
Conditions | Yield |
---|---|
In toluene under Ar, stirred for 30 min at room temp.; removal of solvent in vac., dissolved in benzene, addn. of pentane, filtered, filtrate concd. in vac., addn. of pentane, filtered, washed withpentane, dried in vac., recrystd. (benzene/pentane 1:2); elem. anal.; | A 72% B n/a |
hydrogenchloride
hexaphenylditin
barium
A
tetraphenyltin(IV)
B
triphenyltin chloride
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether; ammonia byproducts: BaCl2; NH3 (liquid); (N2); charging of Ba in dry box Schlenk tubes with (SnPh3)2; addn. of THF, cooling to -78°C; condensation of pre-dried liq. NH3 onto react. mixt., reflux for 6 h at -33°C; warming to room temp.; evapn. of NH3, addn. of 1N HCl soln. in Et2O; removal of volatiles in vac., dissolving in Et2O, filtration through Celite padded filter frit, removal of solvent; | A 2% B 70% |
hydrogenchloride
hexaphenylditin
calcium
A
tetraphenyltin(IV)
B
triphenyltin chloride
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether; ammonia byproducts: CaCl2; NH3 (liquid); (N2); charging of Ca in dry box Schlenk tubes with (SnPh3)2; addn. of THF, cooling to -78°C; condensation of pre-dried liq. NH3 onto react. mixt., reflux for 6 h at -33°C; warming to room temp.; evapn. of NH3, addn. of 1N HCl soln. in Et2O; removal of volatiles in vac., dissolving in Et2O, filtration through Celite padded filter frit, removal of solvent; | A 2% B 70% |
hydrogenchloride
hexaphenylditin
A
tetraphenyltin(IV)
B
triphenyltin chloride
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether; ammonia byproducts: SrCl2; NH3 (liquid); (N2); charging of Sr in dry box Schlenk tubes with (SnPh3)2; addn. of THF, cooling to -78°C; condensation of pre-dried liq. NH3 onto react. mixt., reflux for 6 h at -33°C; warming to room temp.; evapn. of NH3, addn. of 1N HCl soln. in Et2O; removal of volatiles in vac., dissolving in Et2O, filtration through Celite padded filter frit, removal of solvent; | A 2% B 70% |
Conditions | Yield |
---|---|
In tetrahydrofuran (under Ar, Schlenk); CuCl added to soln. of Sn-complex in THF, stirred for 10 h at room temp.; solvent evapd., residue suspended in CH2Cl2/pentane, filtered, filtrate evapd.; monitored by NMR, IR; | 70% |
Conditions | Yield |
---|---|
room temp.; | 66% |
bis(triisopropylphosphane)(dihydrido)dichloroosmium(IV)
triphenylstannane
B
triphenyltin chloride
Conditions | Yield |
---|---|
In toluene under Ar atm. suspn. OsH2Cl2(P(i)Pr3)2 in toluene was treated with Ph3SnH and stirred for 2 h at room temp.; soln. was evapd., residue was washed with pentane and dried in vacuo; elem. anal.; | A 52% B n/a |
triphenyl tin (1+); prop-1-yneide
A
2,4-hexadiyne
B
triphenyltin chloride
Conditions | Yield |
---|---|
With iron(III) chloride byproducts: FeCl2; for 2 h; | A 42% B 44% |
1-chloro-5,5-dimethyl-2-hexene
triphenylstannyl isocyanate
A
3-Isocyanato-5,5-dimethyl-hex-1-ene
B
triphenyltin chloride
Conditions | Yield |
---|---|
at 180℃; for 3h; Product distribution; | A 37% B n/a |
(E)-cinnamyl(triphenyl)stannane
A
(Z)-cinnamyl(triphenyl)stannane
B
triphenyltin chloride
C
1-phenylprop-2-enyl(triphenyl)stannane
Conditions | Yield |
---|---|
In chloroform Irradiation (UV/VIS); N2; Sn-compd. soln. irradiation with 300 W high-pressure Hg lamp throughsatd. aq. CuSO4 soln. for 1 h, solvent evapn. (reduced pressure); TLC(PLC) (hexane/DCM 9:1); total yield 55 %, E/Z ratio 53:47; elem. anal.; | A n/a B 30% C n/a |
3,3-dichloro-1,2-diphenylcyclopropene
C
(η5-MeCp)(carbonyl)2Mn(1,2-diphenylcyclopropenylidene)
D
triphenyltin chloride
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: NaCl; Addn. of Cl2C(CPhCPh) soln. to soln. of Mn-complex at -20°C under N2, color changes immediately to red.; Filtn., concg., addn. of pentane to the filtrate, stirring (5 min), sepg. of dark red ppt., recrystn. (toluene/pentane), washing (pentane), drying in vac., elem. anal.; | A n/a B n/a C 25% D n/a |
chloroform
tetraphenyltin(IV)
A
triphenylmethane
B
triphenyltin chloride
Conditions | Yield |
---|---|
at 260℃; |
methylene chloride
triphenylstannane
A
methane
B
triphenyltin chloride
Conditions | Yield |
---|---|
In hexane at 0℃; for 0.0166667h; Product distribution; (13)C Kinetic Isotope Effect k12/k13; |
triphenyltin bromide
benzyl chloride
A
benzyl bromide
B
triphenyltin chloride
Conditions | Yield |
---|---|
With N-benzyl pyridinium halide In acetonitrile at 100℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In acetonitrile; benzene Electrolysis; absence of oxygen and moisture; W-cathode, Zn suspended on Pt-anode, 30 V, 25 mA, 3.0 h, Et4NClO4 electrolyte; sepn. of pptd. product (further crop on addn. of petroleum ether), washing (petroleum ether), drying (vac.); elem. anal.; | 100% |
triphenyltin chloride
para-methylphenylmagnesium bromide
triphenyl(p-tolyl)tin
Conditions | Yield |
---|---|
In diethyl ether | 100% |
In tetrahydrofuran byproducts: MgBrCl; dropwise addn. of Mg-compd. to Sn-compd, refluxed for 5 h, hydrolysed with HCl; evapd., filtered, dried, extd. (toluene), recrystd. (EtOH/toluene); elem. anal.; | 55% |
diethyl naphthalen-1-yl phosphate
triphenyltin chloride
[1]naphthyl-triphenyl stannane
Conditions | Yield |
---|---|
With sodium In ammonia Irradiation (UV/VIS); (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added, the mixt. was UV-irradiated with stirring for 4 h; excess of CH3I was added, NH3 was evapd., the residue was treated with water, extd. with ether, washed with aq. satd. soln. of NaCl, dried over MgSO4, recrystd. in ethanol; | 100% |
2,5-dimethylphenylmagnesium bromide
triphenyltin chloride
Conditions | Yield |
---|---|
In diethyl ether | 100% |
triphenyltin chloride
1-naphthylmagnesiumbromide
[1]naphthyl-triphenyl stannane
Conditions | Yield |
---|---|
100% | |
100% | |
In diethyl ether; toluene reacting in ether; refluxing in toluene; |
O,O-diethyl O-4-bromophenyl phosphate
triphenyltin chloride
1,4-bis(triphenylstannyl)benzene
Conditions | Yield |
---|---|
With sodium In ammonia Irradiation (UV/VIS); (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added, the mixt. was UV-irradiated with stirring for 1.5 h; excess of CH3I was added, NH3 was evapd., the residue was treated with water, extd. with ether, washed with aq. satd. soln. of NaCl, dried over MgSO4, recrystd. in ethanol; | 100% |
With sodium In ammonia (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added; | 0% |
Tetraethyl 1,4-phenylene bis(phosphate)
triphenyltin chloride
1,4-bis(triphenylstannyl)benzene
Conditions | Yield |
---|---|
With sodium In ammonia Irradiation (UV/VIS); (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added, the mixt. was UV-irradiated with stirring for 1.5 h; excess of CH3I was added, NH3 was evapd., the residue was treated with water, extd. with ether, washed with aq. satd. soln. of NaCl, dried over MgSO4, recrystd. in ethanol; | 100% |
With sodium In ammonia Irradiation (UV/VIS); (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added, the mixt. was UV-irradiated with stirring for 2 h; excess of CH3I was added, NH3 was evapd., the residue was treated with water, extd. with ether, washed with aq. satd. soln. of NaCl, dried over MgSO4, recrystd. in ethanol; | 70% |
With sodium In ammonia (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added; | 0% |
diethyl naphthalen-2-yl phosphate
triphenyltin chloride
(2-naphthyl)triphenylstannane
Conditions | Yield |
---|---|
With sodium In ammonia Irradiation (UV/VIS); (C6H5)3SnCl was dissolved in ammonia, Na metal was added until a blue color persisted for 5 min, when the blue color dissapeared, phosphate ester was added, the mixt. was UV-irradiated with stirring for 4 h; excess of CH3I was added, NH3 was evapd., the residue was treated with water, extd. with ether, washed with aq. satd. soln. of NaCl, dried over MgSO4, recrystd. in ethanol; | 100% |
triphenyltin chloride
3,5-(C(CH3)3)2-1-Sn(C6H5)3-1,2,4-C2P3
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: NaCl; reaction in soln. cooled to -30°C; detn. by (31)P NMR; | 100% |
triphenyltin chloride
3,5-(C(CH3)3)2-1-Sn(C6H5)3-1,2,4-C2P3
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: LiCl; reaction in soln. cooled to -30°C; detn. by (31)P NMR; | 100% |
1,2-dimethoxyethane
hexane
[C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF)
triphenyltin chloride
B
hexaphenylditin
Conditions | Yield |
---|---|
Stage #1: [C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF); triphenyltin chloride In tetrahydrofuran for 12h; Schlenk technique; Stage #2: 1,2-dimethoxyethane; hexane Schlenk technique; | A 75% B 100% |
Conditions | Yield |
---|---|
With sulfur; nickel(II) ferrite; potassium carbonate at 90℃; for 19h; | 100% |
triphenyltin chloride
sodium O,O'-di-isopropyl phosphoroselenoate
SnPh3(OO'-diisopropyl phosphoroselenoate)
Conditions | Yield |
---|---|
In not given byproducts: NaCl; stoich. amts., stirring (in CHCl3 or MeNO2, room temp. or refluxing, 1-6h; details not specified); filtration off of NaCl, centrifugation, solvent removal; elem. anal.; | 99% |
triphenyltin chloride
dimethyl amine
triphenyltin(IV) N,N'-dimethylmonothiocarbamate
Conditions | Yield |
---|---|
With carbon oxide sulfide In acetone byproducts: dimethylammonium chloride; molar ratio = 1 : 1 (pptn. on mixing); filtration, evapn. of filtrate (air-stream, crystn.); recrystn. (CHCl3 or acetone); elem. anal.; | 99% |
triphenyltin chloride
diethylamonium N,N'-dimethylmonothiocarbamate
triphenyltin(IV) N,N'-diethylmonothiocarbamate
Conditions | Yield |
---|---|
In acetone byproducts: diethylammonium chloride; molar ratio = 1 : 1 (pptn. on mixing); filtration, evapn. of filtrate (air-stream, crystn.); recrystn. (CHCl3 or acetone); elem. anal.; | 99% |
potassium N,N-dimethylcarbamoselenothioate
triphenyltin chloride
Se-triphenyltin N,N-dimethylcarbamoselenothioate
Conditions | Yield |
---|---|
In dichloromethane byproducts: KCl; CH2Cl2-soln. of the halogeno-compd. was added to a CH2Cl2 suspn. of the excess of Se-compd at 0 °C under Ar, stirring at 25 °C for3 h; soln. was filtered, evapd. in vac., recrystn. from hexane/CH2Cl2 (3:1) at -25 °C, elem. anal.; | 99% |
Conditions | Yield |
---|---|
In sodium hydroxide; dichloromethane byproducts: NaCl; aq. NaOH; 3 equiv. of Sn-compd. in CH2Cl2 was added to a soln. of 1 equiv. of NaVO3 and 2 equiv. of NaOH in H2O, stirring at room temp.; solid was pptd. after several h, CH2Cl2 was removed in vac., soln. was filtered, residue was washed with water and dried, elem. anal.; | 99% |
N-benzyl-4-hydroxybutanamide
triphenyltin chloride
3-benzyl-4-triphenyltinoxy-butyramide
Conditions | Yield |
---|---|
With NaH In dichloromethane dissolving of N-benzyl-4-hydroxy-butyramide in CH2Cl2; addn. to NaH; stirring for 1 h; filtration of excess NaH, addn. of soln. of Ph3SnCl in CH2Cl2; stirring for 4 h; | 99% |
Conditions | Yield |
---|---|
With Ti(N(C(CH3)3)(3,5-C6H3(CH3)2))3 In benzene byproducts: ClTi(N(C(CH3)3)(3,5-C6H3(CH3)2))3; reaction at 20°C; NMR; | 99% |
Conditions | Yield |
---|---|
Stage #1: triphenyltin chloride With naphthalene; lithium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
ammonium tetramethylethylene dithiophosphate
triphenyltin chloride
triphenyl(4,4,5,5-tetramethyl-2-thioxo-1,3,2-dioxaphospholane-2-thiolato)tin
Conditions | Yield |
---|---|
In benzene byproducts: NH4Cl; equimolar amts., stirring (2-3 h, room temp.); crystn. (benzene/petroleum ether); elem. anal.; | 98% |
triphenyltin chloride
Conditions | Yield |
---|---|
In diethyl ether under dry N2, to a suspn. of the starting complex in diethyl ether addn. of (C6H5)3SnCl under stirring at -78°C, the mixt. is slowly warmed to room temp. (90 min); filtn., removal of solvent in vac., recrystn. (CH2Cl2/n-hexane); | 98% |
ammonium 4,4,6-trimethyl-1,3,2-dioxaphosphorinane-2-thione-2-thiolate
triphenyltin chloride
(C6H5)3SnS2PO2(C(CH3)2CH2CH(CH3))
Conditions | Yield |
---|---|
In benzene byproducts: NH4Cl; equimolar amts., stirring (3-4 h); filtration, evapn. (reduced pressure), recrystn. (benzene/petroleum ether); elem. anal.; | 98% |
cesium 4-methylbenzenecarbodithioate
triphenyltin chloride
triphenyltin 4-methylbenzenecarbodithioate
Conditions | Yield |
---|---|
In dichloromethane byproducts: CsCl; Ar-atmosphere; stirring Sn-compd. with slight excess of dithioate (20°C, 30 min); filtration off of CsCl, solvent removal (reduced pressure), crystn. (ether/hexane=1:1); | 98% |
N-benzylidene-dl-alanine ; sodium salt
triphenyltin chloride
(C6H5)3Sn(C6H5CHNCH(CH3)CO2)
Conditions | Yield |
---|---|
In methanol byproducts: NaCl; N2 atmosphere, addn.of hot soln. of Sn compound to hot soln. of sodium salt of Schiff base, stirring (reflux, 3-4 h); centrifugation, filtration, removement of solvent (reduced pressure), crystn. (petroleum ether (b.p. 40-60°C)), recrystn. (MeOH/petroleumether (b.p. 40-60°C)); elem. anal.; | 98% |
For occupational chemical analysis use NIOSH: Organotin Compounds 5504.
The Triphenyltin chloride, with the CAS registry number 639-58-7, is also known as Chlorotriphenyltin. It belongs to the product categories of Analytical Chemistry; Classes of Metal Compounds; Environmental Endocrine Disruptors; Sn (Tin) Compounds; Tin Compound (Environmental Endocrine Disruptors); Typical Metal Compounds; Organotin Halides Stable Isotopes; Alphabetical Listings; Organometallic Reagents; Organotin. Its EINECS number is 211-358-4. This chemical's molecular formula is C18H15ClSn and molecular weight is 385.46. What's more, its systematic name is Chloro(triphenyl)stannane. Its classification codes are: (1)Agricultural Chemical; (2)Drug / Therapeutic Agent; (3)Fungicide, bactericide, wood preservative; (4)Molluscicide; (5)Mutation data; (6)Organometallic; (7)Reproductive Effect. It is a colourless solid that dissolves in organic solvents. It slowly reacts with water. The main use for this compound is as a fungicide and antifoulant. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides and acids. This substance is able to control diseases of leaf spot of beet, potato blight, brown spot of rice. It is also good for inhibiting reproduction of musca domestica and insect.
Physical properties of Triphenyltin chloride are: (1)ACD/LogP: 2.807; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.81; (4)ACD/LogD (pH 7.4): 2.81; (5)ACD/BCF (pH 5.5): 80.06; (6)ACD/BCF (pH 7.4): 80.06; (7)ACD/KOC (pH 5.5): 801.82; (8)ACD/KOC (pH 7.4): 801.82; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Flash Point: 199.683 °C; (13)Enthalpy of Vaporization: 62.227 kJ/mol; (14)Boiling Point: 397.125 °C at 760 mmHg; (15)Vapour Pressure: 0 mmHg at 25°C.
Uses of Triphenyltin chloride: it can be used to produce 4-(4-triphenylstannanyl-buta-1,3-diynyl)-morpholine at the ambient temperature. It will need solvent diethyl ether with the reaction time of 4 hours. The yield is about 40%.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. It can cause burns. This substance is very toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. You must take off immediately all contaminated clothing. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). This material and its container must be disposed of as hazardous waste. You should avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: Cl[Sn](c1ccccc1)(c2ccccc2)c3ccccc3
(2)Std. InChI: InChI=1S/3C6H5.ClH.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H;/q;;;;+1/p-1
(3)Std. InChIKey: NJVOZLGKTAPUTQ-UHFFFAOYSA-M
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | 210mg/kg (210mg/kg) | Archiv fuer Experimentelle Veterinaermedizin. Vol. 40, Pg. 307, 1986. | |
mouse | LD50 | intraperitoneal | 21500ug/kg (21.5mg/kg) | Journal of the Indian Chemical Society. Vol. 67, Pg. 740, 1990. | |
mouse | LD50 | intravenous | 18mg/kg (18mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01649, | |
mouse | LD50 | oral | 18mg/kg (18mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C314, 1991. | |
rat | LD50 | oral | 135mg/kg (135mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C314, 1991. |
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