Tributyltin Chloride

Liquid

Colorless liquid

Soluble in the common organic solvents, including alcohol, heptane, benzene, and toluene.

Insoluble in cold water but hydrolyzes in hot water

Liquid

Colorless liquid; [HSDB] Unpleasant odor; [MSDSonline]

Danger

H301+H311 (53.6%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 194 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Chemical: Stannane, tributylchloro-

Hazard Traits - Bioaccumulation; Environmental Persistence

Stannane, tributylchloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Stannane, tributylchloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 13-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13798

Tributyltin chloride: HSNO Approval: HSR004733 Approved with controls

Causes tremor and ataxia in lethal dose animal studies; Toxicity includes hepatitis; [RTECS] Highly irritating to eyes; Very toxic to marine organisms; [Sax] Hydrolyzed by water; An irritant; Can be absorbed through skin; [MSDSonline] See Tin, organic compounds. See Bis(tri-n-butyltin)oxide.

Acute Tox. 3 (100%)

Acute toxicity (Oral) - Category 3

Acute toxicity (Oral) - Category 3

UN 3146; Organotin cmpd, solid, not otherwise specified

UN 2788; Organotin cmpd, liquid, not otherwise specified

IMO 6.1; Organotin cmpd, liquid or solid, not otherwise specified

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.

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.

0.1 [mg/m3], as Sn

0.2 [mg/m3], as Sn

TERRESTRIAL FATE: If tributylchlorostannane is released to soil, it will dissociate and form tributyltin(SRC). Tributyltin will be expected to strongly bind to soil(1). Tributyltin is susceptible to biodegradation and is reported to have a half-life in soil of 15-20 weeks(2). Tributyltin may slowly photodegrade on the soil surface(3) but would not be expected to volatilize from near-surface soil(4,5).

AQUATIC FATE: If tributylchlorostannane is released to water, it is expected to dissociate to form tributyltin cations(1). Tributyltin is stable (as defined by lack of debutylation) in distilled, deionized water kept in the dark at 20 °C for over 63 days at pH between 2.9 and 10.3(2) and no degradation of tributyltin was observed in 11 months in KCN-poisoned water sediment mixtures(3). Tributyltin is susceptible to biodegradation in water with half-lives of between 6 days and 35 weeks reported in water and water-sediment mixtures, many of which had been previously contaminated with tributyltin species(3,4). Results from experiments in water and water sediment mixtures have indicated that abiotic degradation of tributyltin species will be limited to direct photolysis in surface water(2,3,5). The half-life for sunlight photolysis of tributyltin was determined to be >89 days both in distilled water and lake water(2). Based upon Kocs of up to 90,800, tributyltin may strongly bind to sediment(3,6,7). Based upon BCFs of >6,000(8), tributyltin cation can strongly bioconcentrate in various aquatic organisms(SRC). Based upon laboratory observations(2) and the fact that tributyltin cationis the dominant species in water, volatilization from water is not expected to be an important environmental pathway for tributylchlorostannane(SRC).

AQUATIC FATE: Radiolabeled tributyltin was added to a 13 cu m marine mesocosm with near natural water column and benthos in summer and monitored for 278 days to study the behavior of tributyltin and its degradation products(1). The removal of tributyltin from the water column was the result of biological degradation, scavenging to the sediment and presumed loss to the atmosphere with an overall removal half-life of 6-12 days(1). Tributyltin compounds in seawater are degraded in summer to give dibutyltins, hydroxylated tributyltins, hydroxylated dibutyltins, carboxylated derivatives and monobutyltin(2). Laboratory studies show that the half-life of tributyltin in sediment is in the range of years(3). Degradation is slower under anaerobic conditions than under aerobic conditions; half-lives in anaerobic sediment is in the range of 2-3 years(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tributylchlorostannane, which has an estimated vapor pressure of 0.013 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase tributylchlorostannane 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 9.0 hours(SRC), calculated from its rate constant of 43X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). There are no experimental studies relating to tributylchlorostannane's photodegradation in air. However, tributyltin species present in water solutions have been observed to slowly photodegrade in sunlight(4).

Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (L308, A182, A184)

If tributylchlorostannane is released to soil, it will dissociate to form tributyltin(SRC). Tributyltin will be expected to strongly bind to soil; tributyltin should not leach through soil(2). No leaching of tributyltin was observed in several soils (clay, sand, topsoil and silt) during periods as long as 16 weeks(2). Tributyltin binds strongly to sediment with the distribution constant for Toronto Harbor sediment and water as 2180 at 20 °C(3). Very little tributyltin or inorganic tin was released from unshaken sediment in 10 months. However, other studies have shown that tributyltin does not adsorb appreciably to suspended particulate matter and that it is primarily associated with the dissolved fraction of estuarine water(1,4). This is in line with the observation that addition of humic acids or kaolin clay material does not significantly affect the tributyltin BCF in mussels(5), suggesting that tributyltin species are only weakly bound to these materials(5). Studies on the adsorption of tributyltin to a wide variety of sorbents yield sorption coefficients ranging from 110 to 350,000 l/kg, but the majority of sorption coefficients are about 1,000 L/kg(6). Adsorption is relatively fast (hours) and reversible. In a 278-day marine mesocosm experiment, the transport rate from the water column to sediment was 0.045/day(7). The distribution coefficient between dissolved state and particulate matter calculated from data between days 2-19 was 60,000 (standard deviation 30,000). Other investigators obtained distribution constants for adsorption of tributyltin to particulate matter and sediment of 3400-9300 L/kg and 200-55,000 L/kg, respectively; values were a function of sediment type and location(7). The Freundlich parameters, log k and 1/n, for tributyltin to sediment were 1.07 and 0.359, respectively(8).

Levels of tributyltin in mussels from San Diego Bay have declined after restrictions on the use of antifouling paint containing tributyltin in California were enacted. Tributyltin levels in mussels from various sites in the bay ranged from 140 to 2100 ng/g wet weight in February 1988 and 100-460 ng/g in February 1990(1). Mean tributyltin concns in American oysters from Sarah Creek, Virginia were 834 ug/kg wet wt(3). Maximum values were 1570 ug/kg and oysters collected in a pristine area contained mean levels of 9 ug/kg. The levels of tributyltin in mussel tissue (n=9) in the Sado Estuary, Portugal were 16-114 ng/g dry wt(2).

Tributylchlorostannane's production and use as an intermediate(1) may result in its release to the environment through various waste streams(SRC). Tributylchlorostannane's production and former use as an rodenticide(1) may have resulted in its direct release to the environment(SRC). Potential sources of organotin compounds in the Rhine River in Germany are the manufacture and industrial use of organotin compounds and the effluents of municipal sewage treatment plants(2). Municipal wastewater has been shown to contain considerable quantities of tributyltin that may be released in surface water(3).

Tributyltin degraded with a half-life of 20 weeks in Toronto Harbor water in the dark at 20 °C; dibutyltin, monobutyltin and inorganic tin was detected as products(1). The half-life of tributyltin present in sediment-water mixtures was shorter than in water alone, 16 weeks at 20 °C in the dark. The detection of small quantities of methyltributyltin in the experiments with non-sterile mixtures of lake water and sediment and in water alone indicates that microorganisms are present that can methylate tributyltin(1). Half-lives as low as 6 and 7 days have been reported for incubation in water from a harbor in San Diego Bay in the presence of light and absence of light, respectively; at a clean water site, the respective half-lives were 9 and 19 days(2). The experimenters ruled out direct photolysis in these experiments as a cause of the increased degradation rate. In a marine mesocosm experiment, the biodegradation rate calculated from the gross removal rate less adsorption and volatilization transport rates was 0.08/day (half-life 9 days) at 20 °C. Other reported degradation half-lives for tributyltin include: 5.5 mo (marine sediment); 4 mo (aerobic freshwater/sediment); 2 mo (seawater at 5 °F); 6-19 days (estuarine waters) 6 days (freshwater at 5 °F); 6-17 days estuarine water; 4-13 days (estuarine water)(3).

SEDIMENT: The concn of tributyltin species in sediment (upper 2 cm) from Toronto Harbor (6 sites) was 0.08-1.28 mg Sn/kg dry weight(1). The concn of tributyltin in sediment from two harbors along the Rhine River in Germany were 13 and 182 ng Sn/g dry wt; the high level is from a small harbor that is crowded with pleasure crafts that are believed to be responsible for large releases of tributyltin(2). The concns of tributyltin in harbor sediment in Lake Lucerne, Switzerland was high, up to 2800 ug/g(3). High concns were restricted to the upper 7 cm and decreased significantly below. The dating of cores suggest that tributyltin may persist for more than a decade in sediment. Small amounts of the mono- and di-butyltin were also found in the upper layers of sediment(3).

MARINE SEDIMENT: While concns of tributyltin in surface water in San Diego Bay declined after restrictions on the use of antifouling paint containing tributyltin in California were enacted. Tributyltin levels in sediment were variable and did not reflect the decreases in levels in the water column. Mean tributyltin levels at 14 sites ranged from 7 to 430 ng/g dry wt between Jan 1989 and July 1990 with the higher values being at yacht basins and naval yards(1). Intertidal sediments at a restricted site downstream from the shipyards in the Sado estuary, Portugal reached levels of 520 ng/g dry wt for tributyltin, over an order of a magnitude higher than samples taken in March(2). This has been ascribed to the cleaning of ships in spring and points up the large seasonal variability in anthropogenic organotin levels. Intertidal and marine levels of tributyltin at other sites in the Sado Estuary were 12-21 and 21 ng/g, respectively. Sediment tributyltin concns from Chesapeake Bay include: 141-1390 ug/kg dry wt at six stations in or near marinas on a northern tributary; 23-290 ug/kg dry wt in Sarah and Kings Creek in Virginia and 920-1300 ug/kg dry wt in the Sarah Creek area(3).

Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (L308)

Used as a rodenticide, in rodent repellant cable coatings, and as an intermediate; Not currently registered with the EPA for use as pesticide in the US; [HSDB] Use as pesticide including biocides and industrial chemical for public use severely restricted in the EU; [eChemPortal: ESIS]

For Tributylchlorostannane (USEPA/OPP Pesticide Code: 083107) 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./

Rodenticide, rodent-repellent cable coating /Former use/

Intermediate

Triorganic tin compounds are widely used as industrial biocides. Agricultural chemicals, wood preservatives, and marine antifoulants. Tribuyltins, along with triphenyltins, and tricyclohexyltins are generally the most useful as biological control agents. /Triorganotins/

Tributyltins are the main active ingredients in certain biocides used to control a broad spectrum of organisms, and are also used in wood preservation, marine paints (as antifouling pesticides), and textiles and industrial water systems (as antifungal agents). (L307)

All Other Chemical Product and Preparation Manufacturing

Stannane, tributylchloro-: ACTIVE

The use of tributyltin compounds in antifoulants are restricted because of their toxicity to aquatic organisms and EPA is cooperating in international efforts for a global phase-out.

The stoichiometric reaction of Grignard or alkylaluminum reagents with stannic chloride to give trialkyltin chloride usually gives a mixture of products. Only in a few cases is it possible to alkylate tin tetrachloride directly to the triorganotin in good yield with few by-products using a Grignard reagent.