Conditions | Yield |
---|---|
In not given tin compd. was heated at 65°C under vac.; | A n/a B 100% |
Conditions | Yield |
---|---|
decompn. at 25°C within 8 h; | A 75.3% B n/a C n/a |
decompn. at 25°C within 8 h; | A 75.3% B n/a C n/a |
β-(cyclohexylthio)ethyl tri-n-butyltin sulfide
A
β-(cyclohexylthio)ethyl mercaptan
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
With silica gel In dichloromethane; pentane | A 64% B 27% |
tributylethynyltin
μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine]
A
ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 0.5h; | A 56% B n/a |
A
1-(N,N-diethylamino)cyclopentene
B
(CH3CH2CH2CH2)3SnOC5H7
C
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
byproducts: H2O, NH(C2H5)2; decompn. at 100°C for 6 h; | A 56% B 5% C n/a |
byproducts: H2O, NH(C2H5)2; decompn. at 100°C for 6 h; | A 56% B 5% C n/a |
n-butyllithium
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether under N2, Schlenk setup, 1:1 mixt., n-BuLi soln. in THF added to soln. of tin compd. in Et2O (1:1), stirred for 10 h at room temp.; water added, org. layer septd., dried (Na2SO4), evapd., elem. anal.; | 55% |
Acetonyltributylstananne
(C4H9)3SnN(C2H5)Sn(C4H9)3
A
(C4H9)3SnCH2C(CH3)N(C2H5)
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
A 40% B n/a | |
A 40% B n/a |
water
bis(tri-n-butyltin)
A
tributylphenylstannane
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar; addn. of freshly prepd. THF soln. of PhEuI to mixt. of THF and Bu3SnSnBu3, mixing at 25°C for 3 h, decompn. of react. mixt. with water acidified with HCl; thin layer chromy.; | A 25% B 23% |
tri-n-butyl-tin hydride
N,N-dimethyl-formamide
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
CpFe(CO)2(Ph3P)Me In not given heating for 48 h at 90°C; | 5% |
dicarbonyl(cyclopentadienyl)methyliron(II) In not given Irradiation (UV/VIS); for 12 h at ambient temp.; | 1% |
methyl-tricarbonyl(η-cyclopentadienyl)molybdenum In not given Irradiation (UV/VIS); for 12 h at ambient temp.; | 1% |
Conditions | Yield |
---|---|
With sodium hydroxide | |
Multi-step reaction with 2 steps 1: tetrahydrofuran 2: air View Scheme | |
Multi-step reaction with 2 steps 1: hexane View Scheme |
5-methyl-1-hexene
1-dodecyne
tributyltin chloride
9-bora-bicyclo[3.3.1]nonane
A
(Z)-2-Methyl-7-octadecen
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In not given byproducts: H2O; |
4-methylquinoline 1-oxide
tri-n-butyl-tin hydride
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In not given byproducts: H2O; |
Conditions | Yield |
---|---|
In water (CH3(CH2)3)3SnCl hydrolyzed; recrystd. from benzene; |
Na(1+)*OSn(C4H9)3(1-)=NaOSn(C4H9)3
tributyltin chloride
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In methanol; toluene byproducts: NaCl; (Ar); Schlenk tube technique; Bu3SnCl in toluene was added dropwise to NaOSn(C4H9)3 in methanol; mixt. was refluxed for 6 h; NaCl was centrifuged; solvent was removed in vac.; residue was distd. under reduced pressure; elem. anal.; |
Conditions | Yield |
---|---|
In not given byproducts: H2O; |
Conditions | Yield |
---|---|
In toluene equimolar amts.; | |
In toluene equimolar amts.; |
Conditions | Yield |
---|---|
byproducts: H2O; | |
byproducts: H2O; on melting; |
Conditions | Yield |
---|---|
In not given byproducts: CHCl3; hydrolysis;; | |
In not given byproducts: CHCl3; hydrolysis;; |
tributyl-tribromomethyl-stannane
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In not given byproducts: CHBr3; hydrolysis;; | |
In not given byproducts: CHBr3; hydrolysis;; |
Phenylsulfonylmethyl-tri-n-butylzinn
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
With air | |
With air | |
With air |
(C4H9)3SnONC(NH2)CH3
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
distn. at 180°C / 0.1 Torr; | |
distn. at 180°C / 0.1 Torr; |
Ethyl-(tributyl-stannyl)-sulfit
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
With water byproducts: C2H5OH, SO2; |
(C4H9)3SnONC(NH2)C2H5
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
distn. at 180°C / 0.1 Torr; | |
distn. at 180°C / 0.1 Torr; |
Conditions | Yield |
---|---|
With H2O byproducts: CH3COCH2CH(CH3)2; rapid hydrolysis; |
(C4H9)3SnONC(NH2)C3H7
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
distn. at 180°C / 0.1 Torr; | |
distn. at 180°C / 0.1 Torr; |
Conditions | Yield |
---|---|
With water hydrolysis; | |
With H2O hydrolysis; |
Tributylzinnester des Acetylglycins
benzylamine
A
(C6H5CH2NH3)(1+)*(CH3CONHCH2COO)(1-)
B
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In 1,4-dioxane; water dioxane:water=6:1, room temp., 4 h; | A >99 B n/a |
In 1,4-dioxane; water dioxane:water=6:1, room temp., 4 h; | A >99 B n/a |
Phenyl glycidyl ether
tributyl(1-chloro-3-phenoxy-2-propanyloxy)stannane
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide const. temp. (+/-1°C) in range 363-393 K in air or nitrogen atmosphere; monitoring by concn. accumulation of chloride ion (potentiometric anal.); |
N-acetyl-D,L-valine
bis(tri-n-butyltin)oxide
N-acetyl-DL-CH3CH(CH3)CHNHCOO-tri-n-butyltin
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
byproducts: H2O; | 100% |
In toluene byproducts: H2O; azeotropic dehydration with toluene; recrystn. (benzene) or sublimation; |
bis(tri-n-butyltin)oxide
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
(C4H9)3SnOCH2C7H5O5(CH3)4
Conditions | Yield |
---|---|
byproducts: H2O; dehydration of 1:2 mixt. of Bu3SnOSnBu3 and alc.; separation of water by distn. or azeotropic distn. in benzene or toluene; | 100% |
byproducts: H2O; dehydration of 1:2 mixt. of Bu3SnOSnBu3 and alc.; separation of water by distn. or azeotropic distn. in benzene or toluene; | 100% |
Conditions | Yield |
---|---|
In tetrachloromethane byproducts: (C4H9)3SnOCHO; 23 h;; | 100% |
In tetrachloromethane byproducts: (C4H9)3SnOCHO; 23 h;; | 100% |
Conditions | Yield |
---|---|
In benzene | 100% |
In benzene | 100% |
92% |
bis(tri-n-butyltin)oxide
Propiolic acid
Propiolsaeure-tri-n-butylstannylester
Conditions | Yield |
---|---|
In benzene byproducts: H2O, dicarboxylate; mole ratio of (C4H9)3SnOSn(C4H9)3 and carboxylic acid 1:2; at 20°C or at reflux temp. to remove of water formed by azeotropic distn.; | 100% |
bis(tri-n-butyltin)oxide
acetone oxime
Isopropylidenaminooxy-tributyl-stannan
Conditions | Yield |
---|---|
In toluene 1:2; azeotropic dehydration; 2 h; | 100% |
In benzene 1:2; azeotropic dehydration; 2 h; | 100% |
In benzene 1:2; azeotropic dehydration; 2 h; | 100% |
heptafluorobutyric Acid
bis(tri-n-butyltin)oxide
Tributyl-heptafluorbutyroxy-zinn
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
byproducts: H2O; | 100% |
Perfluorooctanoic acid
bis(tri-n-butyltin)oxide
Tributyl-perfluoroctanoyloxy-zinn
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
byproducts: H2O; | 100% |
2-Trifluoromethylbenzimidazole
bis(tri-n-butyltin)oxide
1-(tri-n-butylstannyl)-2-trifluoromethylbenzimidazole
Conditions | Yield |
---|---|
In benzene to a soln. of imidazole-compd. was added a soln. of Sn-compd., refluxed for 3.5 h; cooled to room temp., evapn., elem. anal.; | 100% |
3-oxo-1,4-benzothiazin-2-ylacetic acid
bis(tri-n-butyltin)oxide
Tributylzinn-dihydro-oxo-benzothiazin-acetat
Conditions | Yield |
---|---|
byproducts: H2O; | 100% |
bis(tri-n-butyltin)oxide
N,N'-di(4-hydroxybenzyl)isopthalamide
C6H4(CONHCH2C6H4OSn(C4H9)3)2
Conditions | Yield |
---|---|
In toluene byproducts: H2O; stoichiometric ratio, refluxing (20 h); cooling, evapn., drying (vac., 2 h); | 100% |
1-hydroxy-pyrrolidine-2,5-dione
bis(tri-n-butyltin)oxide
(C4H9)3SnONC4H4O2
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: H2O; heating in 2/1 ratio and gradually evacuating (50-1 mm) for 30-40 min; IR; elem.anal.; | 99.7% |
In neat (no solvent) byproducts: H2O; heating; elem. anal.; | 99.7% |
heating; | >99 |
heating; | >99 |
Conditions | Yield |
---|---|
byproducts: H2O; B(OH)3 excess; 160°C; | 99% |
byproducts: H2O; B(OH)3 excess; 160°C; | 99% |
bis(tri-n-butyltin)oxide
1,2,3-tris(tributyltinoxy) propane
Conditions | Yield |
---|---|
With glycerol In neat (no solvent) glycerol to bis(tributyltin) oxide ratio 2:3; mixed, heated at 100-150°C for 1 h at P=50 mm; evacuated to P=1 mm for 0.5 h, heated at 190-220°C; distd., IR, elem. anal.; | 99% |
Conditions | Yield |
---|---|
In toluene byproducts: H2O; mixt. of (Bu3Sn)2O and PhSH (1:2 molar ratio) refluxed (12 h) in toluenewith removal of H2O (Dean-Stark apparatus); toluene removed (vac.); residue distd. (vac.); | 99% |
In toluene byproducts: H2O; refluxing for 2 h, removing H2O with a water separator; | 80% |
N-hydroxybenzenecarboximidamide
bis(tri-n-butyltin)oxide
(C4H9)3SnONC(NH2)C6H5
Conditions | Yield |
---|---|
In benzene 1:2; azeotropic dehydration; 2 h; | 99% |
In benzene 1:2; azeotropic dehydration; 2 h; | 99% |
morpholine
maleiimide
bis(tri-n-butyltin)oxide
(C4H9)3Sn(C8H11N2O3)
Conditions | Yield |
---|---|
In methanol amine and maleimide added to soln. of trialkyltin oxide in CH3OH (molar ratio 10:2:1), refluxed for half h; evapn.; | 99% |
2,3-dibromomaleimide
bis(tri-n-butyltin)oxide
N-tributylstannyl-2,3-dibromomaleimide
Conditions | Yield |
---|---|
In not given byproducts: H2O; solvent toluene or heptane; azeotropic removal water and solvent, recrystn.; elem. anal.; | 99% |
In water; benzene to a soln. of (Bu3Sn)2O in benzene was added imide in water (molar ratio oxide/imide = 1/2); shaking at room temp. for 15-20 min, org. layer was separated, water layer washed with benzene; org. layers were combined; drying over MgSO4, evapn.; | 96% |
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In methanol at 25℃; for 24h; | 99% |
5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-hydroxymethyl-1H-imidazole
methyl isocyanate
bis(tri-n-butyltin)oxide
Conditions | Yield |
---|---|
In tetrahydrofuran | 98% |
Conditions | Yield |
---|---|
With acetic acid byproducts: H2O; heating; | 98% |
With CH3COOH byproducts: H2O; heating; | 98% |
With acetic acid In benzene byproducts: H2O; |
bis(pinacolato)diborane
bis(tri-n-butyltin)oxide
(C4H9)3SnOBO2C2(CH3)4
Conditions | Yield |
---|---|
1:1; 130°C; distn.; | 98% |
1:1; 130°C; distn.; | 98% |
bis(tri-n-butyltin)oxide
2,2'-bis-(1,2-dihydro-4-oxo-3,1-benzoxazine)
Conditions | Yield |
---|---|
In benzene byproducts: H2O; in refluxing benzene; H2O was removed as azeotrope of benzene; elem. anal.; | 98% |
(β-carboxyethyl)diallylisocyanurate
bis(tri-n-butyltin)oxide
diallyl 2-[(tributylstannyloxy)carbonyl]ethyl isocyanurate
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: H2O; heating in 2/1 ratio and gradually evacuating (50-1 mm) for 30-40 min; IR; elem.anal.; | 98% |
In neat (no solvent) byproducts: H2O; heating; elem. anal.; | 98% |
bis(tri-n-butyltin)oxide
(C4H9)3SnOOCC6I4COOCH2CH(C6H13)C8H17-2
Conditions | Yield |
---|---|
In benzene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
In toluene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
In toluene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
In benzene byproducts: H2O; 1:2 mole ratio; azeotropic removal of water; | 98% |
Ethyl propionate
bis(tri-n-butyltin)oxide
3-tert-butyl-isoxazole-5-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
In toluene | 97% |
In toluene | 97% |
phosphonic acid diethyl ester
bis(tri-n-butyltin)oxide
O-ethyl-O'-tri-n-butylstannyl phosphonate
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: diethylether; (Ar); addn. of TBTO to phosphonate with stirring, heating to 10°C (4 h); concn. in vac. at 40-80°C; elem. anal.; | 97% |
In not given (Ar); excess of diethylphosphonate; (31)P-NMR spectroscopic monitoring; |
Conditions | Yield |
---|---|
by heating at 140°C for 1 h; | 97% |
by heating at 90-100°C for 1.25 h; | 97% |
by heating at 140°C for 1 h; | 97% |
by heating at 90-100°C for 1.25 h; | 97% |
bis(trimethylsilyl)mercury
bis(tri-n-butyltin)oxide
A
bis(tri-n-butyltin)
B
Bu3SnOSiMe3
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% |
1. Introduction of Bis(tributyltin) oxide
The Tributyltin oxide, with the CAS registry number 56-35-9, is also known as Bis(tri-n-butyltin)oxide. It belongs to the product categories of Industrial/Fine Chemicals; Organometallics. Its IUPAC name is called tributyl(tributylstannyloxy)stannane. This chemical's classification codes are Agricultural Chemical; Anti-Infective Agents; Disinfectants; Fungicide, bactericide, wood preservative; Fungicides, industrial; Immunologic Factors; Immunosuppressive agents; Molluscicide; Mutation data; Organometallic; Pesticides; Reproductive Effect; Skin / Eye Irritant; Tumor data.
2. Properties of Bis(tributyltin) oxide
(1)ACD/LogP: 3.84; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5; (4)ACD/LogD (pH 7.4): 5; (5)ACD/BCF (pH 5.5): 3840; (6)ACD/BCF (pH 7.4): 3840; (7)ACD/KOC (pH 5.5): 12801; (8)ACD/KOC (pH 7.4): 12801; (9)#H bond acceptors: 1; (10)#Freely Rotating Bonds: 20; (11)Flash Point: 240.979 °C; (12)Enthalpy of Vaporization: 71.007 kJ/mol; (13)Boiling Point: 474.847 °C at 760 mmHg; (14)Vapour Pressure: 0 mmHg at 25°C.
3. Structure Descriptors of Bis(tributyltin) oxide
(1)Canonical SMILES: CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC
(2)InChI: InChI=1S/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3
(3)InChIKey: APQHKWPGGHMYKJ-UHFFFAOYSA-N
4. Toxicity of Bis(tributyltin) oxide
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LCLo | inhalation | 200mg/m3 (200mg/m3) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: AGGRESSION LUNGS, THORAX, OR RESPIRATION: DYSPNEA | European Journal of Toxicology and Environmental Hygiene. Vol. 9, Pg. 339, 1976. |
mouse | LD50 | intraperitoneal | 12500ug/kg (12.5mg/kg) | Russian Pharmacology and Toxicology Vol. 42, Pg. 73, 1979. | |
mouse | LD50 | intravenous | 6mg/kg (6mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | European Journal of Toxicology and Environmental Hygiene. Vol. 9, Pg. 31, 1976. |
mouse | LD50 | oral | 55mg/kg (55mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(5), Pg. 10, 1976. | |
mouse | LD50 | skin | 163mg/kg (163mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989. |
rabbit | LD50 | skin | 900mg/kg (900mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | European Journal of Toxicology and Environmental Hygiene. Vol. 9, Pg. 31, 1976. |
rabbit | LDLo | oral | 50mg/kg (50mg/kg) | Sangyo Igaku. Japanese Journal of Industrial Health. Vol. 15, Pg. 3, 1973. | |
rat | LC50 | inhalation | 64uL/m3/4H (0.064mL/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Technical Information Service. Vol. OTS0572027, |
rat | LD50 | intraperitoneal | 5mg/kg (5mg/kg) | BEHAVIORAL: COMA GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION | National Technical Information Service. Vol. OTS0571270, |
rat | LD50 | oral | 87mg/kg (87mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1255, 1986. | |
rat | LD50 | skin | > 300mg/kg (300mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | National Technical Information Service. Vol. OTS0571915, |
5. Safety Information of Bis(tributyltin) oxide
Hazard Symbols:T;N
Risk Codes:
R21:Harmful in contact with skin.
R25 :Toxic if swallowed.
R36/38:Irritating to eyes and skin.
R23/25:Toxic by inhalation and if swallowed.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Description:
S35:This material and its container must be disposed of in a safe way.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
6. Preparation of Bis(tributyltin) oxide
Bis(tributyltin) oxide can be prepared by anhydrous tin tetrachloride and butyl bromide. This reaction will need reagent KOH.
Sn+2Cl2 → SnCl4
C4H9OH+HCl → C4H9Cl+H2O
3Mg+3C4H9Cl+SnCl4 → (C4H9)3SnCl+MgCl2
2(C4H9)3SnCl+2NaOH → C24H54OSn2+NaCl+H2O
7. Use of Bis(tributyltin) oxide
Bis(tributyltin) oxide, is an organotin compound chiefly used as a biocide (fungicide and molluscicide), especially a wood preservative. Tributyltin compounds had been used as marine anti-biofouling agents. Concerns over toxicity of these compounds have led to a worldwide ban by the International Maritime Organization. It is now considered a severe marine pollutant.
8. Other details of Bis(tributyltin) oxide
When you are using bis(tributyltin) oxide, please be cautious about it as the following:
Bis(tributyltin) oxide that at low level can cause damage to health. It may present an immediate or delayed danger to one or more components of the environment. In addition, it is irritating to eyes and skin. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
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