ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト：[email protected]AIアクセス：llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
戻る
化工社化工社 化学情報印刷レポート · 研究参考用
HCID 5948作成日：2026年10月27日

トリブチルスタンナン

水素化トリブチルすず · ヒドリドトリブチルすず(IV) · トリブチルすず(IV) · トリブチルすずヒドリド · トリブチルすず · トリブチルヒドリドすず(IV) · 水素化トリ-N-ブチルすず · 水素化トリブチルスズ(Ⅳ)

https://huagongshe.com/ja/chemical/5948

トリブチルスタンナン の分子構造式

識別子と物理属性

CAS No.688-73-3
分子式C12H28Sn
平均分子量291.06 g/mol
単同位体質量292.121303 g/mol
SMILESCCC[CH2][SnH]([CH2]CCC)[CH2]CCC
InChIKeyDBGVGMSCBYYSLD-UHFFFAOYSA-N
PubChem CID5948
ChEBICHEBI:27086
EC No.211-704-4
DTXSIDDTXSID0040709
現地名トリブチルスタンナン

化学・物理的性質

極性表面積0
水素結合供与体数0
水素結合受容体数0
回転可能結合数9
重原子数13
形式電荷0
複雑度72
密度1.103 @ 20 °C1.082 g/mL at 25 °C(lit.)
Color/FormA liquid.
沸点112.5-113.5 @ 8 mm Hg80 °C0.4 mm Hg(lit.)
DecompositionWhen heated to decomposition it emits acrid smoke & irritating fumes.
Physical DescriptionLiquid[Hawley] Colorless liquid[MSDSonline]
融点<0°C
蒸気圧5 hPa (20 °C)
屈折率n20/D 1.473(lit.)
引火点104 °F
貯蔵条件Store below +30°C.
外観・状態液体
比重1.103 (20℃)
色無色
溶解度反応する
BRN3587329
InChI1S/3C4H9.Sn/c3*1-3-4-2/h3*1,3-4H2,2H3
InChIKeyPIILXFBHQILWPS-UHFFFAOYSA-N
CAS データベース688-73-3(CAS DataBase Reference)
NISTの化学物質情報Tri-n-butyltin hydride(688-73-3)
EPAの化学物質情報Tributyltin (688-73-3)

化学的特性

clear colourless liquid

安全性と法規制

GHS 分類DangerH226 (13%): Flammable liquid and vapor [Warning Flammable liquids]H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]H312 (100%): 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]H372 (100%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]H400 (97.1%): 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]P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P273, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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. For more detailed information, please visit ECHA C&L website.
規制情報Hazard Traits - BioaccumulationEnvironmental PersistenceAuthoritative List - Canada PBiTsReport - if used as a fragrance or flavor ingredientCouncil Regulation (EEC) No 315/1993Status: Active Update: 20-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/23311Tributyltin hydride: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報IMAP assessments - Stannane, tributyl-: Environment tier I assessmentIMAP assessments - Stannane, tributyl-: Human health tier I assessment
有害性の概要In inhalation lethal dose studies, causes lacrimation, dyspnea, and seizures

用途

解説

トリブチルスタンナン，無色の液体．沸点78～81 ℃(105 Pa)．n25D 1.471．湿気によりヒドロキシトリブチルスズに分解する．有機ハロゲン化合物の還元や不飽和結合への付加，すなわちヒドロスタニル化剤として用いられる．森北出版「化学辞典（第2版）

使用

Tributyltin hydride the most commonly used tin hydride，it is less toxic than the more volatile trierhyl and trimethyl analogues, and it is therefore the most widely used organostannane.Tributyltin hydride, the reagent of choice for generating alkyl radical, is also widely used in aryl radical cyclization. Other reagents developed for this purpose include samarium diiodide, palladium reagents organosilanes as well as manganese triacetate and transition metals for carbocyclization.

製法・合成法

純化方法

Dissolve it in Et2O, add quinol (500mg for 300mL, to stabilize it), dry over Na2SO4, filter, evaporate and distil it under dry N2. It is a clear liquid if dry and decomposes very slowly. In the presence of H2O, traces of tributyl tin hydroxide are formed in a few days. Store it in sealed glass ampoules in small aliquots. It is estimated by reaction with aqueous NaOH when H2 is liberated. CARE: stored samples may be under pressure due to liberated H2. [Van Der Kerk et al. J Appl Chem 7 366 1937, Ono et al. Tetrahedron 41 4013 1985, Neuman Synthesis 665 1987, Curran Synthesis 417 1988, Beilstein 4 IV 4312.]

[ChemIDplus] Can cause skin burns
[Sullivan, p. 979] A skin and eye irritant
[eChemPortal: ERMA] Produces flammable gases on contact with water
An irritant
Can be absorbed through skin
[MSDSonline] See ORGANOMETALS. See Tin, organic compounds.
Hazard Classes and CategoriesFlam. Liq. 3 (13%)Acute Tox. 3 (100%)Acute Tox. 4 (100%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT RE 1 (100%)Aquatic Acute 1 (97.1%)Aquatic Chronic 1 (100%)
Shipping Name/ Number DOT/UN/NA/IMOUN 3146Organotin cmpd, solid, not otherwise specifiedUN 2788Organotin cmpd, liquid, not otherwise specifiedIMO 6.1Organotin cmpd, liquid or solid, not otherwise specified
暴露管理・個人防護0.02 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
処分方法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.
Threshold Limit Values (TLV)0.1 [mg/m3], as Sn0.2 [mg/m3], as Sn8 hr Time Weighted Avg (TWA): 0.1 mg/cu m15 min Short Term Exposure Limit (STEL): 0.2 mg/cu m. Skin. /Tin, organic cmpd, as Sn/A4Not classifiable as a human carcinogen. /Tin, organic cmpd, 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
健康影響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)
生態毒性値LC90 Schistosoma mansoni miracidia 32.0 ug/l/hr. /Conditions of bioassay not
環境中動態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 °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 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), tri-n-butyltin hydride, which has an estimated vapor pressure of 0.04 mm Hg at 25 °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 °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).
有害作用Neurotoxin - Other CNS neurotoxinOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Dermatotoxin - Skin burns.ACGIH Carcinogen - Not Classifiable.
暴露経路Oral (L308)inhalation (L308)dermal(L308)
毒性の概要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-alpha, 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 SymptomsInorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)
Soil Adsorption/MobilityBased upon the moisture sensitivity of the chemical(1,2), adsorption of tri-n-butyltin hydride to sediments and suspended particulate matter in natural waters and to soil is not expected to be an important process(SRC). According to a classification scheme(3), its hydrolysis product, tributyltin, is expected to be immobile in soil(SRC). No leaching of tributyltin was observed in several soils (clay, sand, topsoil and silt) during periods as long as 16 weeks(4). Tributyltin binds strongly to sediment with the distribution constant for Toronto Harbor sediment and water as 2180 at 20 °C(5). 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(6,7). This is in line with the observation that addition of humic acids or kaolin clay material does not significantly affect the measured tributyltin BCF in mussels(8), suggesting that tributyltin species are only weakly bound to these materials(SRC). 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(9). Adsorption is relatively fast (hours) and reversible(9). In a 278-day marine mesocosm experiment, the transport rate from the water column to sediment was 0.045/day(10). The distribution coefficient between dissolved state and particulate matter calculated from data between days 2-19 was 60,000 (standard deviation 30,000)(10). 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(10). The Freundlich parameters, log k and 1/n, for tributyltin to sediment was 1.07 and 0.359, respectively(11).
Natural Pollution SourcesOrganic tin does not occur naturally. /Organic tin/
Artificial Pollution SourcesTri-n-butyltin hydride's production and use as a reducing agent for the conversion of alkyl halides to hydrocarbons(1) and as a synthetic intermediate for other butyltin compounds(2,3), and its formation during the analysis for other tributyltin compounds(4) may result in its release to the environment through various waste streams(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(5). Municipal wastewater has been shown to contain considerable quantities of tributyltin that may be released in surface water(6).
Environmental BiodegradationTributyltin degraded with a half-life of 20 weeks in Toronto Harbor (Canada) 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(1). 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(2). 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(2). 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).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
F1-10
水環境危害等級（WGK）3
TSCA 収載状態TSCA listed
RTECS 番号WH8675000
輸送番号（UN）UN 1993 3/PG 3
PRTR法第一種指定化学物質
税関コード29310095
危険文句（R）10-21-25-36/38-48/23/25-50/53-15-67-65-11
安衛法57,57-2
消防法危-4-2-III
危険表示T,N,F
安全措置（S）35-36/37/39-45-60-61-62-36/37-33-26-16
危険等級6.1Acute Tox. 3 OralAcute Tox. 4 DermalAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Flam. Liq. 3Repr. 1BSkin Irrit. 2STOT RE 1
包装等級II
自然発火温度>250 °C
貯蔵分類3 - Flammable liquids
有害物質データ688-73-3(Hazardous Substances Data)