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Bis(tributyltin) oxide

CAS：56-35-9
MW:596.115
MF：C24H54OSn2

TBTO (bis(tri-n-butyltin)oxide) appears as thin, colourless to pale yellow, flammable andcombustible liquid. It is soluble in organic solvents. TBTO, or bis(tri-n-butyltin)oxide, is anorganotin compound used as a biocide, fungicide, and molluscicide. Uses of tributyltin alsoinclude as an anti-fouling chemical in marine paints for boats, anti-fungal agent in textilesand industrial water systems, in cooling tower and refrigeration water systems, wood pulppreservative in paints and paper mill systems, inner surfaces of cardboard, and in the manufacturingprocesses of leather goods, textiles, wood, plastics, and mothproof stored garments.In fact, TBT compounds are considered the most hazardous of all tin compounds. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Bis(tributyltin) oxide

1.2 Synonyms: BIS(TRI-N-BUTYLTIN) OXIDE; BTO; CAR-BAN(R); Distannoxane, 1,1,1,3,3,3-hexabutyl-; EINECS 200-268-0; HBD; HEXABUTYLDISTANNOXANE; MFCD00009418; TBTO; TBTO(R); TBTO(TM); tributyl(tributylstannyloxy)stannane; Tributyltin oxide;

1.3 CAS No.: 56-35-9

1.4 CID: 16682746

1.5 EINECS: 200-268-0

1.6 Molecular Formula: C24H54OSn2

1.7 Inchi: InChI=1S/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;;;

1.8 InChkey: APQHKWPGGHMYKJ-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC

1.10 Isomers Smiles: CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC

2. Properties

2.1 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.2 AnalyticLaboratory Methods: EPA Method EPA-B PMD-TQO. Determination of bis(Tri-n-butyltin) Oxide; in Wood Preservatives by Internal Standard Gas Chromatography.

2.3 Appearance: Clear colorless liquid

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: Clear colorless liquid

2.6 Color/Form: Slightly yellow liquid.

2.7 Contact Allergens: Tributyl tin oxide is used as an antifouling and biocideagent against fungi, algae, and bacteria, particularly inpaints. Sometimes used in chemistry, tributyltin oxide isa strong irritant. Bis(tributyltin) oxide Preparation Products And Raw materials Preparation Products

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2.8 Decomposition: When heated to decomposition it emits acrid and irritating fumes.

2.9 Odor: Weak odor

2.10 Physical: PHYSICAL DESCRIPTION: Clear pale yellow liquid. Toxic by skin absorption or inhalation of vapors. Used as a bactericide, fungicide and chemical intermediate.

2.11 Water Solubility: INSOLUBLE

2.12 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.13 StorageTemp: +4°C

3. Use and Manufacturing

3.1 Description: Bis(tributyltin) oxide (CAS 56-35-9) is a white solid compound that is commonly used in various industrial applications. It has a basic structure consisting of tributyltin cations (Bu3Sn+) and oxide anions (O2-), forming a polymeric network. This chemical is insoluble in water, but it can dissolve in organic solvents such as benzene and toluene. It has a melting point of around 90-95°C and a boiling point of approximately 260-270°C.

Applicable Fields
Biocides: Bis(tributyltin) oxide is widely used as a biocide in various industries. Its mechanism of action involves inhibiting the growth of microorganisms, such as bacteria and fungi, by disrupting their cell membranes. It is commonly used in antifouling paints for marine applications to prevent the attachment of organisms to ship hulls.

Plastics Industry: In the plastics industry, this chemical is utilized as a heat stabilizer and flame retardant. It helps to improve the thermal stability of plastics and reduce their flammability. The mechanism of action involves forming a protective layer on the surface of the plastic, which inhibits the release of flammable gases.

Agriculture: Bis(tributyltin) oxide is also used in agriculture as a pesticide. It acts as a molluscicide, targeting snails and slugs by disrupting their nervous system. It is commonly used in agricultural fields and gardens to protect crops from damage caused by these pests.

Storage Conditions
Store in a cool, dry place.

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3.2 General Description: Clear pale yellow liquid. Toxic by skin absorption or inhalation of vapors. Used as a bactericide, fungicide and chemical intermediate.

3.3 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 241 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 4 of 241 companies. For more detailed information, please visit ECHA C&L website

Of the 14 notification(s) provided by 237 of 241 companies with hazard statement code(s):

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
H312 (96.62%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H331 (38.82%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H335 (13.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H360 (11.39%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H372 (61.6%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
H373 (38.4%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501

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3.4 Methods of Manufacturing: Hydrolysis of tributyl tin chloride.

3.5 Usage: Bis(tributyltin) Oxide is an organotin compound used as a fungicide and molluscicide, particularly in wood preservation. Bis(tributyltin) Oxide was used as an active component in marine antifouling paints but is not longer used due to its toxicity and is considered a severe marine pollutant.

4. Safety and Handling

4.1 Exposure Standards and Regulations: Bis(tri-n-butyltin) oxide is an indirect food additive for use as a preservative only as a component of adhesives.

4.2 Octanol/Water Partition Coefficient: log Kow= 3.84

4.3 Fire Hazard: Bis(tributyltin) oxide is probably combustible.

4.4 Other Preventative Measures: Employees who handle ... bis(tri-n-butyltin)oxide ... should wash their hands thoroughly with soap or mild detergent & water before eating, smoking, or using toilet facilities.
If ... bis(tri-n-butyltin)oxide ... gets on the skin, immediately flush with large amounts of water, then wash with soap or mild detergent & water. If ... bis(tri-n-butyltin)oxide ... soaks through the clothing, remove the clothing immediately & flush with large amounts of water & then wash using soap or mild detergent & water. Get medical attention immediately.
Eating & smoking should not be permitted in areas where ... bis(tri-n-butyltin)oxide ... is handled, processed, or stored.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

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4.5 Cleanup Methods: Do NOT wash away into sewer. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.

4.6 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.7 Fire Fighting Procedures: Provision to contain effluent from fire extinguishing.
In case of fire in the surroundings: all extinguishing agents allowed.

4.8 FirePotential: Combustible.

4.9 Formulations/Preparations: USEPA/OPP Pesticide Code 083001; Trade Names: Self polishing copolymer, TBTO, Biomet, Biomet 75, AW 75-D, Butinox, Bio-met TBTO, Bis(tri-N-butyltin)oxide, BTO, SN-9, ENT 24,979, L.S. 3394.

4.10 Protective Equipment and Clothing: Employees should be provided with & required to use impervious clothing, gloves, face shields (8-inch minimum), & other appropriate protective clothing necessary to prevent repeated or prolonged skin contact with ... liquid bis(tri-n-butyltin)oxide ... .
Non-impervious clothing which becomes contaminated with ... bis(tri-n-butyltin)oxide ... should be removed promptly & not reworn until the contaminant is removed from the clothing.
Clothing contaminated with ... bis(tri-n-butyltin) oxide ... should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of contaminant from the clothing. If the clothing is laundered or otherwise cleaned to remove the contaminant, the person performing the operation should be informed of contaminant's hazardous properties.
Employees should be provided with & required to use dust- & splash-proof safety goggles where ... liquids containing ... bis(tri-n-butyltin)oxide ... may contact the eyes.
Ventilation, local exhaust, or breathing protection.

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4.11 Skin, Eye, and Respiratory Irritations: Exposure to tributyltin can produce irritation of the eyes and throat ... and mucous membrane irritation.

4.12 Sensitive: Air & Moisture Sensitive

4.13 Toxicity: LD50 oral in rat: 87mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 repeated exposure, Category 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H372 Causes damage to organs through prolonged or repeated exposure H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P362+P364 Take off contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P314 Get medical advice/attention if you feel unwell. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : liquid film

Mass

7. Synthesis Route

56-35-9Total: 43 Synthesis Route

688-73-3 67 Suppliers

56-35-9 53 Suppliers

682-00-8 3 Suppliers

56-35-9 53 Suppliers

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8. Precursor and Product

precursor:

688-73-3

1461-23-0

682-00-8

5764-62-5

681-95-8

1733-68-2

681-94-7

1066-87-1

1461-22-9

1067-52-3

product:

56-36-0

1461-25-2

994-89-8

683-18-1

1528-01-4

688-73-3

682-00-8

994-71-8

813-19-4

681-94-7

9. Computed Properties

Molecular Weight：596.115g/mol
Molecular Formula：C₂₄H₅₄OSn₂
Compound Is Canonicalized：True
XLogP3-AA：596.22128
Monoisotopic Mass：598.22187
Complexity：246
Rotatable Bond Count：20
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：1
Topological Polar Surface Area：9.2
Heavy Atom Count：：27
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcfB4IAAAAAAAAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGAAAAAAACACAAAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: Bis(tri-n-butyltin) oxide is employed in the synthesis of α,β-unsaturated methyl ketones, isoxazoles.

BRN: 745057

Description: TBTO (bis(tri-n-butyltin)oxide) appears as thin, colourless to pale yellow, flammable and combustible liquid. It is soluble in organic solvents. TBTO, or bis(tri-n-butyltin)oxide, is an organotin compound used as a biocide, fungicide, and molluscicide. Uses of tributyltin also include as an anti-fouling chemical in marine paints for boats, anti-fungal agent in textiles and industrial water systems, in cooling tower and refrigeration water systems, wood pulp preservative in paints and paper mill systems, inner surfaces of cardboard, and in the manufacturing processes of leather goods, textiles, wood, plastics, and mothproof stored garments. In fact, TBT compounds are considered the most hazardous of all tin compounds.

View all

Chemical Properties: Clear colorless liquid

Uses: Bis(tributyltin) Oxide is an organotin compound used as a fungicide and molluscicide, particularly in wood preservation. Bis(tributyltin) Oxide was used as an active component in marine antifouling paints but is not longer used due to its toxicity and is considered a severe marine pollutant.

Uses: Bis(tributyltin) oxide is widely used in Europe for the preservation of timber, millwork, and wood joinery, eg, window sashes and door frames. It is applied from organic solution by dipping or vacuum impregnation. It imparts resistance to attack by fungi and insects but is not suitable for underground use. An advantage of bis(tributyltin) oxide is that it does not interfere with subsequent painting or decorative staining and does not change the natural color of the wood.

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Uses: Tributyltin oxide is used as an antifouling and biocide agent against fungi, algae and bacteria in paints and is an irritant.

General Description: Clear pale yellow liquid. Toxic by skin absorption or inhalation of vapors. Used as a bactericide, fungicide and chemical intermediate.

Air & Water Reactions: Insoluble in water.

Reactivity Profile: Bis(tributyltin) oxide may react vigorously with oxidizing agents and with reducing agents.

Hazard: Toxic via ingestion and inhalation.

Health Hazard: ACUTE/CHRONIC HAZARDS: Bis(tributyltin) oxide is toxic by ingestion and inhalation and is a skin and eye irritant.

Fire Hazard: Bis(tributyltin) oxide is probably combustible.

Contact allergens: Tributyl tin oxide is used as an antifouling and biocide agent against fungi, algae, and bacteria, particularly in paints. Sometimes used in chemistry, tributyltin oxide is a strong irritant.

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