Tributylzinnchlorid

tributylchlorostannane · TRIBUTYLTIN CHLORIDE · TBTC · TRI-N-BUTYLTIN CHLORIDE · TBTCL · CHLOROTRIBUTYLTIN · Tributylstannyl chloride · Tributylzinnchlorid

https://huagongshe.com/de/chemical/15096

Identifikatoren & physikalische Daten

CAS No.	1461-22-9
Summenformel	C12H27ClSn
Durchschnittliche Molmasse	325,5 g/mol
Monoisotopische Masse	326,08232324 g/mol
SMILES	CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC
InChIKey	GCTFWCDSFPMHHS-UHFFFAOYSA-M
PubChem CID	15096
ChEBI	CHEBI:79734
EC No.	215-958-7
DTXSID	DTXSID3027403
Lokaler Name	Tributylzinnchlorid

Chemische & physikalische Eigenschaften

Polarare Oberfläche (TPSA)	0
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	0
Frei drehbare Bindungen	9
Schwere Atome	14
Formalladung	0
Komplexität	104
Stoffklassen	Metals -> Tin Compounds, Organic
LogP (Verteilungskoeffizient)	log Kow = 4.76
Dichte	1.20 @ 20 °C/4 °C1.2 g/mL at 25 °C(lit.)
Color/Form	LiquidColorless liquid
Löslichkeit	Soluble in the common organic solvents, including alcohol, heptane, benzene, and toluene.Insoluble in cold water but hydrolyzes in hot water0.017g/lPRACTICALLY INSOLUBLE
Endocrine Disruptors	Potential endocrine disrupting compound
Siedepunkt	171-173 °C @ 25 mm Hg171-173 °C25 mm Hg(lit.)
Decomposition	When heated to decomp it emits toxic fumes of /hydrogen chloride/.
Dampfdruck	0.00927 [mmHg]<0.01 mm Hg ( 20 °C)
Food Contact Substances	FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Brechungsindex	Index of refraction = 1.4903 @ 25 °Cn20/D 1.492(lit.)
Physical Description	LiquidColorless liquid[HSDB] Unpleasant odor[MSDSonline]
Schmelzpunkt	-9 °C
Flammpunkt	>230 °F
Lagerbedingungen	2-8°C
Aggregatzustand	liquid
Wichte	1.186
Farbe	colorless
BRN	3535715
Stabilität	Hygroscopic
InChIKey	GCTFWCDSFPMHHS-UHFFFAOYSA-M
LogP (Verteilungskoeffizient)	2.21 at 23℃
CAS Datenbank	1461-22-9(CAS DataBase Reference)
NIST chemische Informationen	Tri-n-butyltin chloride(1461-22-9)
EPA chemische Informationen	Tributyltin chloride (1461-22-9)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH301+H311 (53.6%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oralacute 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.H301: Toxic if swallowed [Danger Acute toxicity, oral]
Regulatorische Informationen	Chemical: Stannane, tributylchloro-Hazard Traits - BioaccumulationEnvironmental PersistenceStannane, 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/13798Tributyltin chloride: HSNO Approval: HSR004733 Approved with controls
Gefahrenübersicht	Causes tremor and ataxia in lethal dose animal studiesToxicity includes hepatitis[RTECS] Highly irritating to eyesVery toxic to marine organisms[Sax] Hydrolyzed by waterAn irritantCan be absorbed through skin[MSDSonline] See Tin, organic compounds. See Bis(tri-n-butyltin)oxide.
Hazard Classes and Categories	Acute Tox. 3 (100%)Acute toxicity (Oral) - Category 3
Shipping Name/ Number DOT/UN/NA/IMO	UN 3146Organotin cmpd, solid, not otherwise specifiedUN 2788Organotin cmpd, liquid, not otherwise specifiedIMO 6.1Organotin cmpd, liquid or solid, not otherwise specified
Skin, Eye, and Respiratory Irritations	A severe eye irritant.
Expositionsschutz und Persönliche Schutzausrüstung	0.1 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
Entsorgungsverfahren	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.
Preventive Measures	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.
Threshold Limit Values (TLV)	0.1 [mg/m3], as Sn0.2 [mg/m3], as Sn
Permissible Exposure Limit (PEL)	0.1 [mg/m3], as Sn
Immediately Dangerous to Life or Health (IDLH)	25.0 [mg/m3], as Sn
Gesundheitliche Auswirkungen	Breathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308)
Umweltverhalten	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 conditionshalf-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).
Unerwünschte Wirkungen	Neurotoxin - Other CNS neurotoxin
Expositionspfade	Oral (L308)inhalation (L308)dermal (L308)
Toxizitätsübersicht	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)
Signs and Symptoms	Inorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)
Soil Adsorption/Mobility	If tributylchlorostannane is released to soil, it will dissociate to form tributyltin(SRC). Tributyltin will be expected to strongly bind to soiltributyltin 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, respectivelyvalues 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).
Fish/Seafood Concentrations	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).
Artificial Pollution Sources	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).
Environmental Biodegradation	Tributyltin degraded with a half-life of 20 weeks in Toronto Harbor water in the dark at 20 °Cdibutyltin, 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, respectivelyat 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 water4-13 days (estuarine water)(3).
Sediment/Soil Concentrations	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 wtthe 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 tributary23-290 ug/kg dry wt in Sarah and Kings Creek in Virginia and 920-1300 ug/kg dry wt in the Sarah Creek area(3).
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).
F	3-9-21
Wassergefährdungsklasse (WGK)	3
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 2788 6.1/PG 3
Zollcode	29310095
RTECS-Nr.	WH6820000
R-Sätze (R)	21-25-36/38-48/23/25-50/53
Gefahrensymbole	T,N
Sicherheitshinweise (S)	35-36/37/39-45-60-61-26
Gefahrenklasse	6.1
Verpackungsgruppe	II
Gefahrstoffdaten	1461-22-9(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

Tributyltin Chloride is a triorganotin compound with insecticidal acitivity. It is an endocrine disruptor as well as an inhibitor for the V-ATPases (potential targets in the treatmen t of diseases such as osteoporosis and cancer). Tributyltin Chloride has the functions of antiseptic, sterilization and mildew proof and widely used in wood preservation, ship paint, etc. Further, it is used in hot end glass coating and rodent-repellent for cable coatings.

Herstellung & Synthese

synthetische

Tributyltin chloride is prepared by a redistribution reaction by combining stannic chloride and tetrabutyltin: 3 (C4H9)4Sn + SnCl4 → 4 (C4H9)3SnCl.