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| CAS No.: | 56-35-9 |
|---|---|
| Name: | Bis(tributyltin) oxide |
| Article Data: | 71 |
| Molecular Structure: | |
|
|
|
| Formula: | C24H54OSn2 |
| Molecular Weight: | 596.112 |
| Synonyms: | Bis(tributyltin)oxide (6CI);Distannoxane, hexabutyl- (8CI,9CI);6-Oxa-5,7-distannaundecane,5,5,7,7-tetrabutyl-;Aceto TBTO;BioMeT 66;BioMeT SRM;BioMeT TBTO;Bis(tributylstannic oxide);Bis(tributylstannyl) ether;Bis(tributylstannyl)oxide;Butinox;Di-tributyl tin oxide;Distannoxane,1,1,1,3,3,3-hexabutyl-;Hexabutyldistannoxane;Hexabutylditin oxide;Intercide 340A;Lastanox F;Lastanox Q;Lastanox Q1;Lastanox Super;Lastanox T;Lastanox T 20;MT 1E;Mykolastanox F;NSC 22332;NSC 28132;Oxybis(tributylstannane);Oxybis[tributyltin];Stannicide A;Stannicide O;TBTO;TnBTO;Tri-n-butyltin oxide;Tributyltin oxide;Vikol AF25;Vikol LO 25; |
| EINECS: | 200-268-0 |
| Density: | 1.17g/mLat 25°C(lit.) |
| Melting Point: | -45 °C |
| Boiling Point: | 474.847 °C at 760 mmHg |
| Flash Point: | 240.979 °C |
| Solubility: | insoluble in water |
| Appearance: | Clear colorless liquid |
| Hazard Symbols: |
 T, N
|
| Risk Codes: | 21-25-36/38-48/23/25-50/53 |
| Safety: | 35-36/37/39-45-60-61 |
| Transport Information: | UN 2788 |
| PSA: | 9.23000 |
| LogP: | 9.69460 |
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| 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 |
- 73622-44-3
β-(cyclohexylthio)ethyl tri-n-butyltin sulfide
A
- 10160-81-3
β-(cyclohexylthio)ethyl mercaptan
B
- 56-35-9
bis(tri-n-butyltin)oxide
| Conditions | Yield |
|---|---|
| With silica gel In dichloromethane; pentane | A 64% B 27% |
- 994-89-8
tributylethynyltin
- 88016-29-9
μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine]
A
- 125803-61-4
ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate
B
- 56-35-9
bis(tri-n-butyltin)oxide
| Conditions | Yield |
|---|---|
| In dichloromethane at 0℃; for 0.5h; | A 56% B n/a |
A
- 34969-48-7
1-(N,N-diethylamino)cyclopentene
B
- 17851-95-5
(CH3CH2CH2CH2)3SnOC5H7
C
- 56-35-9
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 |
- 109-72-8, 29786-93-4
n-butyllithium
- 56-35-9
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% |
- 28483-60-5
Acetonyltributylstananne
- 38900-20-8
(C4H9)3SnN(C2H5)Sn(C4H9)3
A
- 61385-73-7
(C4H9)3SnCH2C(CH3)N(C2H5)
B
- 56-35-9
bis(tri-n-butyltin)oxide
| Conditions | Yield |
|---|---|
| A 40% B n/a | |
| A 40% B n/a |
- 7732-18-5
water
- 813-19-4
bis(tri-n-butyltin)
A
- 960-16-7
tributylphenylstannane
B
- 56-35-9
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% |
- 688-73-3
tri-n-butyl-tin hydride
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 56-35-9
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 |
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Consensus Reports
Standards and Recommendations
ACGIH TLV: TWA 0.1 mg(Sn)/m3; STEL 0.2 mg(Sn)/m3 (skin).
DFG MAK: 0.0021 ppm (0.05 mg/m3)
NIOSH REL: (Organotin Compounds) TWA 0.1 mg(Sn)/m3
Analytical Methods
Specification
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).