Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Tributyltin methacrylate

Tributyltin methacrylate

Tributyltin methacrylate structure

Tributyltin methacrylate 

structure
  • CAS No:

    2155-70-6

  • Formula:

    C16H32O2Sn

  • Chemical Name:

    Tributyltin methacrylate

  • Synonyms:

    2-Propenoic acid,2-methyl-,tributylstannyl ester;Stannane,tributyl(methacryloyloxy)-;Stannane,tributyl[(2-methyl-1-oxo-2-propenyl)oxy]-;Tributyltin methacrylate;Tin,tributyl(methacryloyloxy)-;Methacrylic acid,tributylstannyl deriv.;Tributylstannyl methacrylate;Tributyl(methacryloxy)stannane;Tin tributylmethacrylate;(Methacryloyloxy)tributylstannane;Tributylmethacryloyloxystannane;NSC 221239;154194-72-6

Description

TRIBUTYLTIN METHACRYLATE is a liquid. Irritates skin and eyes.


Tributyltin methacrylate is a liquid. Irritates skin and eyes.


Tributyltin methacrylate is a liquid. Irritates skin and eyes.

Tributyltin methacrylate Basic Attributes

375.12500

375.13

218-452-4

BQ3J70T6UN

221239

2788

DTXSID9035204

2916140000

Characteristics

26.30000

5.45150

Tributyltin methacrylate is a liquid. Irritates skin and eyes.

1.5651 g/cm3 @ Temp: 20 °C

20-22 °C

138.5°C

>76°C

1.4811

In water, 13 mg/L at 25 deg C (est)

below 5ºC

2.25X10-4 mm Hg at 20 deg C

Henry's Law constant = 8.5X10-6 atm-cu m/mol at 25 °C (est)

When heated to decomposition it emits acrid smoke and irritating fumes|No rapid reaction with air. No rapid reaction with water.|Hydroxyl radical reaction rate constant = 6.1X10-11 cu cm/molecule-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Organometallics

Polymerizable

TRIBUTYLTIN METHACRYLATE is in the family of tin compounds widely used as stabilizers for plastics, additives to paint(as antifouling agents). Some have catalytic properties. Examples include butyl tin, dibutyl tin oxide. Their main hazard is associated with their high toxicity, in skin adsorption or inhalation.

Safety Information

II

3.1

UN 2788

23/24/25

20/21-36/37/39

P264, P270, P273, P301+P310, P321, P330, P391, P405, P501

H301

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

USEPA, Office of Water; Ambient Aquatic Life Water Quality Criteria for Tributyltin (TBT)- Final. EPA 822-R-03-031 (December 2003). This document provides guidance to States and Tribes authorized to establish water quality standards under the Clean Water Act (CWA) to protect aquatic life from acute and chronic effects of tributyltin.[Available from, as of November 7, 2014: http://www.epa.gov/waterscience/criteria/tributyltin/tbt-final.pdf]|WHO; Environ Health Criteria 116: Tributyltin compounds (1990).[Avalable from, as of November 7, 2014: http://www.inchem.org/documents/ehc/ehc/ehc116.htm]

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Respirator Recommendations: Up to 1 mg/cu m: /Tin (organic compounds, as Sn)/ [Table#6913]|Respirator Recommendations: Up to 2.5 mg/cu m: /Tin (organic compounds, as Sn)/ [Table#6914]|Respirator Recommendations: Up to 5 mg/cu m: /Tin (organic compounds, as Sn)/ [Table#6915]|Respirator Recommendations: Up to 25 mg/cu m: /Tin (organic compounds, as Sn)/ [Table#6916]|For more Personal Protective Equipment (PPE) (Complete) data for TRIBUTYLTIN METHACRYLATE (6 total), please visit the HSDB record page.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Skin and eye irritant. Inhalation of aerosols leads to respiratory irritation. /Tributyltin compounds/

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 0.1 mg/cu m. /Tin, organic compound, as Sn/|Vacated 1989 OSHA PEL TWA 0.1 mg/cu m, skin designation, is still enforced in some states. /Tin, organic compounds, as Sn/

Recommended Exposure Limit: 10 hour Time-Weighted Average: 0.1 mg/cu m, skin. (Note: The REL applies to all organic tin compounds except Cyhexatin). /Tin (organic compounds, as Sn)/|Recommended Exposure Limit: 10 hr Time-Weighted Avg: 2 mg/cu m. /Tin/

Toxicity

IDENTIFICATION AND USE: Tributyltin compounds have been registered as molluscicides, and used as antifoulants on boats, ships, quays, buoys, crabpots, fish nets, and cages as wood preservatives; as slimicides on masonry; as disinfectants; and as biocides for cooling systems, power station cooling towers, pulp and paper mills, breweries, leather processing, and textile mills. HUMAN EXPOSURE AND TOXICITY: Skin and/or eye lesions have been reported after exposure of workers during the manufacturing and formulation of tributyltin compounds. Severe dermatitis has been reported after direct contact with the skin. Inhalation of aerosol leads to respiratory irritation. Exposure of the general public may come from the contamination of food, particularly fish and shellfish, and from the domestic application of wood preservatives. ANIMAL STUDIES: Tributyltin methacrylate is highly toxic and has pronounced cumulative properties. Its threshold concentration in rats, judging by its organoleptic index of noxiousness, amounts to 0.064 mg/L, which corresponds to a level of 0.1 mg/L in water bodies. Tributyltin compounds exhibit greater lethal potential when administered parenterally, as opposed to orally, probably due to only partial absorption from the gut. Other effects of acute exposure may include alterations in blood lipid levels, the endocrine system, liver, and spleen, and transient deficits in brain development. Teratogenic effects have only occurred in experimental animals that caused overt maternal toxicity. The teratogenic potential of tributyltin compounds is therefore, considered to be very low. One carcinogenicity study on rats has been reported in which neoplastic changes were observed in endocrine organs at 50 mg/kg diet. The pituitary tumors found at 0.5 mg/kg diet are considered as having no biological significance since there was no dose-response relationship. These tumor types appear usually at high and variable background incidences. Based on the results of comprehensive mutagenicity studies, tributyltin compounds are not considered to have mutagenic potential. ECOTOXICITY STUDIES: Tributyltin compounds inhibit oxidative phosphorylation and alter mitochondrial structure and function. Tributyltin interferes with calcification of the shell of oysters (Crassostrea species). Tributyltin has been shown to produce the superimposition of male sexual characteristics on female neogastropod (stenoglossan) snails and one freshwater gastropod (Prosobranchia).

LD50 Mouse oral 160 mg/kg|LD50 Rat oral 160 mg/kg|LD50 Mouse iv 18 mg/kg

/AQUATIC SPECIES/ Tributyltin (TBT) has been shown to produce the superimposition of male sexual characteristics on female neogastropod (stenoglossan) snails and one freshwater gastropod (Prosobranchia), Marisa cornuarietis. This phenomenon, termed "imposex," can result in females with a penis, a duct leading to the vas deferens, and a convolution of the normally straight oviduct. ...Severity of imposex is quantified using relative penis size (RPSI; ratio of female to male penis volume3 x 100) and the six developmental stages of the vas deferens sequence index (VDSI). TBT has been shown to impact populations of the Atlantic dogwhinkle (dogwhelk), Nucella lapillus, which has direct development. /Tributyltin compounds/|/AQUATIC SPECIES/ ...13- and 16-day-old larvae of striped bass (Morone saxatilis) /were exposed/ to varying concentrations of /tributyltin/ (TBT) from methacrylate-painted panels for 6-7 days. They found significant reductions in survival at measured concentrations of 0.766 ug TBT/L or more. At lower exposure concentrations (0.067 ug/L), growth parameters changed in the 13-day-old larvae only. No changes occurred in the growth parameters of 16-day-old larvae exposed to 0.444 ug/liter or less. /It is not known/ whether this apparent difference in sensitivity between larvae of different ages was a true effect or simply the result of differences between the various batches of larvae.|/AQUATIC SPECIES/ ...Eggs, embryos, and larvae of the California grunion (Leuresthes tenuis) to plates painted with 9.4% /tributyltin/ (TBT) methacrylate (0.5% TBTO; 44.7% cuprous oxide; 45.5% inert ingredient) and aged for 30 days in flowing sea water. The authors claimed that the exposure to concentrations of between 0.14 and 1.72 ug TBT per liter had no adverse effect on hatching, growth, or development. In fact the presence of TBT at such concentrations enhanced both hatching success and stimulated growth. A concentration of 10 ug TBT/L had no effect on hatchability, but at 74 ug/L hatching success was reduced by approximately 50%. The authors observed no effect on the survival of larvae, hatched from eggs exposed to concentrations of 0.14 to 1.72 ug/L, up to 7 days post-hatch. The presence of copper, however, should be taken into consideration in the interpretation of these results.|/FIELD STUDIES/ Eastern mud snails, I. obsoleta, collected from the York River, VA near Sarah Creek had no incidence of imposex and contained no detectable tributyltin (TBT) (<0.020 ug/g dry weight). The average TBT concentrations of York River water was 0.0016 ug/L. In contrast, the average TBT concentrations from four locations in Sarah Creek, VA were from 0.010 to 0.023 ug/L, snails contained about 0.1 to 0.73 ug/g TBT and there was a 40 to 100% incidence of imposex. /In another study,/ ...dogwhinkle snails, N. lima, /were collected/ from Auke Bay, AK and ...imposex or TBT in snails from sites far from marinas /was not detected/. Snails from locations near marinas all exhibited imposex and contained 0.03 to 0.16 ug/g TBT dry weight. tissue. /Tributyltin compounds/

Tributyltin methacrylate's production and use as a stabilizer for PVC(1) may result in its release to the environment through various waste streams; its use as a biocide in antifouling paints used to coat ship hulls(2,3) will result in its direct release to the environment(SRC). Registered use in antifouling paints in the US was cancelled by the EPA in 2004(3). Since 2008 Tributyltin has been banned as an anti-fouling paint under a global convention; however, ships previously coated continue to release tributyltin compounds into the environment(4).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4900(SRC), determined from a structure estimation method(2), indicates that tributyltin methacrylate is expected to have slight mobility in soil(SRC). An ester compound analogous to tributyltin methacrylate, tributyltin acetate, does not ionize in distilled water(3); however, tributyltin acetate does ionize in seawater presumably due to an increased ionic strength(3). Therefore, tributyltin methacrylate may exist in a cation form in some environmental scenarios(SRC), and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of tributyltin methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-4 mm Hg(5), and estimated water solubility, 13 mg/L(2). Tributyltin methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). In addition, potential volatilization would be attenuated by strong adsorption to soil(SRC). A 15% of theoretical BOD using activated sludge in the Japanese MITI test indicates that tributyltin methacrylate is not readily biodegradable(6). In this MITI test, the tributyltin methacrylate was reported to hydrolyze in water to form methacrylic acid and tributyltin hydroxide(6). Based on analogy to tributyltin acetate(3), tributyltin methacrylate could ionize to the cation, and the cation will react with hydroxide ions to form tributyltin hydroxide(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4900(SRC), determined from a structure estimation method(2), indicates that tributyltin methacrylate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may occur(3) based upon an estimated Henry's Law constant of 8.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-4 mm Hg(4), and estimated water solubility, 13 mg/L(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9 and 68 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.4 years if adsorption is considered(5). An ester compound analogous to tributyltin methacrylate, tributyltin acetate, does not ionize in distilled water(6); however, tributyltin acetate does ionize in seawater presumably due to an increased ionic strength(6). Therefore, tributyltin methacrylate may exist in a cation form in some environmental scenarios(SRC). According to a classification scheme(7), a estimated BCF of 266(SRC), from an estimated log Kow of 4.14(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Using carp (Cyprinus carpio) which were exposed over an 8-week period, the bioconcentration of tributyltin methacrylate was reported as moderate(actual BCF data not reported)(8). A 15% of theoretical BOD using activated sludge in the Japanese MITI test indicates that tributyltin methacrylate is not readily biodegradable(8). In this MITI test, the tributyltin methacrylate was reported to hydrolyze in water to form methacrylic acid and tributyltin hydroxide(8). Based on analogy to tributyltin acetate(6), tributyltin methacrylate could ionize to the cation, and cation will react with hydroxide ions in natural water to form tributyltin hydroxide(SRC). Tributyltin methacrylate contains an ester moiety(SRC) and esters are potentially susceptible to environmental base-catalyzed hydrolysis with the rate of hydrolysis increasing with increasing pH(3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tributyltin methacrylate, which has a vapor pressure of 2.25X10-4 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tributyltin methacrylate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase tributyltin methacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 1 day(SRC), calculated from its rate constant of 1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tributyltin methacrylate may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of tributyltin methacrylate with photochemically-produced hydroxyl radicals has been estimated as 6.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of tributyltin methacrylate with atmospheric ozone has been estimated as 1.3X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone ml per cu cm(1).|Tributyltin methacrylate contains an ester moiety(SRC) and esters are potentially susceptible to environmental hydrolysis(1). Esters undergo base-catalyzed hydrolysis with the rate of hydrolysis increasing with increasing pH(1). Tributyltin methacrylate reportedly has no rapid reaction with water(2). A Japanese biodegradation MITI test reported that tributyltin methacrylate hydrolyzed in water to form methacrylic acid and tributyltin hydroxide(3), but it was not stated if the hydrolysis was biotic, abiotic or a combination(SRC); total degradation was 15% over 28 days(3). An ester compound analogous to tributyltin methacrylate, tributyltin acetate, does not ionize in distilled water(4); however, tributyltin acetate does ionize in seawater presumably due to an increased ionic strength(4); after ionizing in seawater, the cation can react with hydroxide ion in the water and extraction yields tributyltin hydroxide(4).

An estimated BCF of 266 was calculated in fish for tributyltin methacrylate(SRC), using an estimated log Kow of 4.14(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC). Using carp (Cyprinus carpio) which were exposed over an 8-week period, the bioconcentration of tributyltin methacrylate was reported as moderate (actual BCF data not reported)(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tributyltin methacrylate can be estimated to be 4900(SRC). According to a classification scheme(2), this estimated Koc value suggests that tributyltin methacrylate is expected to have slight mobility in soil. This estimate is consistent with observed tributyltin adsorption to soil and sediment(SRC). Using tributyltin chloride, the tributyltin moiety was strongly adsorbed during aquatic sediment studies with a Koc of 18,197(3); Kd sorption isotherms did vary with pH, salinity and temperature(3). Similar strong adsorption of the tributyltin moiety, from the chloride, was observed in estuarine sediment studies(4,5). The tributyltin moiety, from the chloride, is a cation(3), and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). An ester compound analogous to tributyltin methacrylate, tributyltin acetate, does not ionize in distilled water(7); however, tributyltin acetate does ionize in seawater presumably due to an increased ionic strength(7). Therefore, tributyltin methacrylate may exist in a cation form in some environmental scenarios(SRC). Tributyltin oxide has been observed to preferentially partition from the aqueous phase to particles(8).

The Henry's Law constant for tributyltin methacrylate is estimated as 8.5X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.25X10-4 mm Hg(1), and estimated water solubility, 13 mg/L(2). This Henry's Law constant indicates that tributyltin methacrylate is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 9 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 68 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.4 years if adsorption is considered(4). Tributyltin methacrylate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Tributyltin methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to tributyltin methacrylate may occur through dermal contact with this compound at workplaces where tributyltin methacrylate is produced or used. Use data indicate that the general population may be exposed to tributyltin methacrylate via dermal contact with consumer products, such as antifouling paint for boats, containing tributyltin methacrylate or boat hulls previously coated with paints containing tributyltin methacrylate. (SRC)

Drug Information

Tributyltin is absorbed from the gut (20-50% depending on the vehicle) and via the skin of mammals (approximately 10%).|Tributyltin can be transferred across the blood-brain barrier and from the placenta to the fetus. Absorbed material is rapidly and widely distributed amongst tissues principally liver and kidney and, to a lesser extent, in the spleen, fat, lungs, brain, and muscle. /Tributyltin compounds/|Excretion of tributyltin is via the bile rather than the urine. /Tributyltin compounds/|These compounds exhibit greater lethal potential when administered parenterally, as opposed to orally, probably due to only partial absorption from the gut. /Tributyltin compounds/

/Tributyltin/ (TBT) metabolism also occurs in lower organisms, but it is slower, particularly in molluscs, than in mammals. The capacity for bioaccumulation is, therefore, much greater than in mammals. /Tributyltin compounds/|Metabolism of tributyltin derivatives has been clearly demonstrated in in vitro studies. ...The possible metabolism of /tributyltin/ (TBT) acetate /was studied/ using rat hepatic microsomes in the presence of NADPH. They demonstrated hydroxylation by monooxygenases of the principal carbon-hydrogen bonds (alpha and beta to the tin atom) of 24% (at the alpha position) and 50% (at the beta position). The hydroxylated alpha metabolite is unstable and rapidly splits to form the dibutyl derivative, followed by 1-butanol and then butane. According to /a seperate study/, the same type of reaction occurs in microsome preparations from mice. /Tributyltin compounds/|TBT metabolism in mammals is rapid; metabolites are detectable in blood within 3 hr of TBT administration. In in vitro studies, it has been shown that TBT is a substrate for mixed-function oxidases, but these enzymes are inhibited by very high concentrations of TBT. /Tributyltin compounds/

The rate of TBT loss differs with different tissues, and estimates for biological half-lives in mammals range from 23 to about 30 days. /Tributyltin compounds/

The effects of tin alkyls on electron transfer and oxidative phosphorylation were studied. All tin alkyls effectively inhibit respiration of rat liver mitochondria. The action of bis(tributyl tin)oxide and dibutyl diisooctyl thioglycolate tin on the mitochondria in a state of dissociation is localized in the terminal step of the respiration chain. The other alkyls act in the site located before cytochrome c. The effect of bis(tributyl tin)oxide on ADP-activated respiration and dinitrophenyl-activated ATPase of intact mitochondria is similar to that of oligomycin. These effects might be explained by the presence of 2 electrophilic centers in a molecule of this compound. /Tin alkyls/|Tributyl and triphenyltins cause microtubule disassembly and disruption of the mitotic spindle and other elements of the cytoskeleton. This effect increases with increasing lipophilicity of the tin compound and may involve thio group modification by the organotins. /Organotin Pesticides/|Triorganotins inhibit several important sulfhydryl-dependant enzymes which has been attributed to their coordination with protein sulfhydryls and other functional groups. These enzymes include Na+,K+ ATPase, caspases involved in apoptosis, glutathione S-aryltransferase, hemoglobin, and cytochrome P450-dependant monooxygenases. /Organotin Pesticides/|TBT compounds inhibit oxidative phosphorylation and alter mitochondrial structure and function.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Teratogens

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ Skin and/or eye lesions after exposure of workers during the manufacturing and formulation of tributyltin (TBT) compounds /have been reported/... Severe dermatitis has been reported after direct contact with the skin. /Tributyltin compounds/|/SIGNS AND SYMPTOMS/ Skin and/or eye lesions after exposure of workers during the manufacturing and formulation of tributyltin (TBT) compounds, in the application and removal of TBT paints, and from the use of TBT in wood preservatives /have been reported/.|/SIGNS AND SYMPTOMS/ Severe dermatitis has been reported after direct contact with the skin.The potential problem is made worse by the lack of immediate skin response.|/SIGNS AND SYMPTOMS/ Skin and eye irritant. Inhalation of aerosols leads to respiratory irritation.|For more Human Toxicity Excerpts (Complete) data for TRIBUTYLTIN METHACRYLATE (6 total), please visit the HSDB record page.

TNBSM

Tributyltin methacrylate Use and Manufacturing

Uses

For tributyltin methacrylate (USEPA/OPP Pesticide Code: 083120) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./|/In/ an antifouling paint for use on ship and boat hulls to deter the growth of fouling organisms.|Tributyltin compounds have been registered as molluscicides, as antifoulants on boats, ships, quays, buoys, crabpots, fish nets, and cages, as wood preservatives, as slimicides on masonry, as disinfectants, and as biocides for cooling systems, power station cooling towers, pulp and paper mills, breweries, leather processing, and textile mills. /Tributyltin compounds/|Tributyltin methacrylate is used as a stabiliser for PVC.

`Micron 25R' (containing TBT methacrylate co-polymer).

2-Propenoic acid, 2-methyl-, tributylstannyl ester: ACTIVE|Tributyltin (TBT) compounds are organic derivatives of tetravalent tin. They are characterized by the presence of covalent bonds between carbon atoms and a tin atom... . /Tributyltin compounds/

Health Hazards -> Teratogens

Computed Properties

Molecular Weight:375.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:12
Exact Mass:376.142433
Monoisotopic Mass:376.142433
Topological Polar Surface Area:26.3
Heavy Atom Count:19
Complexity:252
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.