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tri-n-butyltin hydride(CAS No. 688-73-3)

tri-n-butyltin hydride C12H28Sn (cas 688-73-3) Molecular Structure

688-73-3 Structure

Identification and Related Records

【Name】
tri-n-butyltin hydride
【CAS Registry number】
688-73-3
【Synonyms】
Tributyltin hydride
Tri-N-Butyltin hydrine
【EINECS(EC#)】
211-704-4
【Molecular Formula】
C12H28Sn (Products with the same molecular formula)
【Molecular Weight】
291.04
【Inchi】
InChI=1/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;;/rC12H28Sn/c1-4-7-10-13(11-8-5-2)12-9-6-3/h13H,4-12H2,1-3H3
【Canonical SMILES】
CCCC[Sn](CCCC)CCCC
【MOL File】
688-73-3.mol

Chemical and Physical Properties

【Appearance】
Almost colorless liquid.
【Density】
1.082
【Melting Point】
<0°C
【Boiling Point】
80℃ (0.4 mmHg)
【Refractive Index】
1.472-1.474
【Flash Point】
40℃
【Water】
REACTS
【Solubilities】
REACTS
【Color/Form】
A liquid.
【Stability】
Stable under normal temperatures and pressures.
【HS Code】
29310095
【Storage temp】
2-8°C
【Computed Properties】
Molecular Weight:290.05278 [g/mol]
Molecular Formula:C12H27Sn
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:9
Exact Mass:291.113472
MonoIsotopic Mass:291.113472
Topological Polar Surface Area:0
Heavy Atom Count:13
Formal Charge:0
Complexity:72.1
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Hazard Codes】
T:Toxic;N:Dangerousfortheenvironment;
【Risk Statements】
R10;R15;R21;R25;R36/38;R48/23/25;R50/53
【Safety Statements 】
S35;S36/37/39;S45;S60;S61
【HazardClass】
6.1
【PackingGroup 】
II
【Sensitive】
Air & Moisture Sensitive
【Transport】
UN 1993
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Reaction of tributyltin chloride with lithium aluminum hydride or sodium borohydride.
【Usage】
Tributyltin hydride may be used as a reducing agent for the conversion of alkyl halides to hydrocarbons.

Biomedical Effects and Toxicity

【Therapeutic Uses】
MEDICATION (VET): Use as veterinary medicine as poultry anthelmintic.
【Biomedical Effects and Toxicity】
An evaluation was conducted of the effects of trialkyltin compounds on murine erythroleukemic cell nuclei via flow cytometric analysis. The flow cytometric variables which were examined included the cellular DNA synthetic cycle, axial light loss, fluorescein- isothiocyanate fluorecence and 90 degree light scattering. The murine erythroleukemic cells were grown in a suspension culture with cell viability being determined by a carboxyfluorescein-diacetate/propidium-iodide assay. The murine erythroleukemic cells were exposed to trimethyltin, triethyltin, and tributyltin at various concentrations with the effects being assessed by monitoring cell viability, growth rate, and the various flow cytometric parameters. Based upon the carboxyfluorescein-diacetate/propidium-iodide assay, it was determined that toxicity increased in the order trimetyltin, triethyltin, and tributyltin. These alkyltin exposures resulted in mean cellular carboxyfluorescein fluorescent increases which were compound and dosage specific below a critical level. The fluorescence of 3,3'-dihexyloxacarbocyanine-iodide was used to determine plasma membrane potential and demonstrated that tributyltin was most effective in decreasing membrane potential, followed by triethyltin and then trimethyltin. Nuclei isolated from murine erythroleukemic cells were used to determine the effects of these trialkyltin compounds upon the cell cycle. DNA distribution during the cycle, as assessed by flow cytometry, demontrated that a 4 hour exposure to 1 uM tributyltin, 5 uM triethyltin, or 100 uM trimethyltin blocked a particular phase of the cell cycle. Exposures above these maximal levels for the three alkyltin compounds resulted in cell death which correlated with an influx of propidium-iodide. /It was/ concluded that murine erythroleukemic cell toxicity is related to compound lipophilicity and thus, tributyltin is the most toxic of the trialkyltin compounds investigated.
Accumulation & catabolism of tributyltin was measured in blue crabs (Callinectes sapidus) after 16-day exposures to tributyltin-contaminated prey. Tributyltin & the metabolites, dibutyltin & monobutyltin, were separated by gas chromatography & measured by atomic absorption in prey & crab tissues during the 16 day test. Crabs were fed grass shrimp Palaemonetes pugio contaminated with 1.8 ug tributyltin, 0.09 ug dibutyltin & 0.03 ug monobutyltin per gram wet weight tissue. Feeding rates for exposed & non-exposed crabs were equal during the 16 day test. In 16 days, exposed crabs consumed about 2.02 ug of tributyltin. Tributyltin was sequentially debutylated in a significant manner by blue crabs, but not by the grass shrimp. Tributyltin concns peaked in crabs after 4 days of feeding, at 0.12 ug/g wet weight tissue. Dibutyltin peaked at 8 days at 0.39 ug/g wet weight tissue, & monobutyltin peaked at 12 days at 0.35 ug/g wet weight tissue. Total butyltins reached equilibrium by 8 days, but the relative toxic burden declined from 8-16 days because the proportion of tributyltin continued to decline. Growth molting success & feeding rates were not affected in the juvenile crabs during the 16 day test. Catabolism of tributyltin reduces tissue concns of tributyltin, thereby incr the tolerance of blue crabs to tributyltin. /Tributyltin/

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: If tri-n-butyltin hydride is released to soil, it will be subject to hydrolysis based upon its reported water sensitivity(1) and reactivity with proton donors such as hydrogen halides and carboxylic acids(2). The hydrolysis product, tributyltin, will be expected to strongly bind to soil(3). Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). Tributyltin is susceptible to biodegradation and is reported to have a half-life in soil of 15-20 weeks(4). Tributyltin may slowly photodegrade on the soil surface(5) but will not volatilize from near-surface soil(6,7).
AQUATIC FATE: If tri-n-butyltin hydride is released to water, it will be expected to mainly exist as the cation, tributyltin(1). Volatilization from water surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). Tributyltin is stable (as defined by lack of debutylation) in distilled, deionized water kept in the dark at 20 deg 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 measured Koc of up to 90,800, tributyltin may strongly bind to sediment(3,6,7). According to a classification scheme(8), a BCF of >6,000 for tributyltin(9) suggests the potential for bioconcentration in aquatic organisms is very high(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), tri-n-butyltin hydride, which has an estimated vapor pressure of 0.04 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase tri-n-butyltin hydride 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 deg C(SRC) determined using a structure estimation method(3). Tributyltin hydroxide may be susceptible to direct photolysis based upon the adsorption of UV light >290 um by tri-, di-, and monobutyltin compounds(4).

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