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뷰틸주석 트리염화물

Butyltin trichloride

HCID 14236
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1118-46-3
표준 SMILES
CCC[CH2][Sn]([Cl])([Cl])[Cl]
InChIKey
YMLFYGFCXGNERH-UHFFFAOYSA-K
분자식
C4H9Cl3Sn
평균 분자량
282.2 g/mol
단동위원소 질량
281.87917803

개요

Monobutyltin trichloride is an organotin compound. Tin is a chemical element with the symbol Sn and atomic number 50. It is a natural component of the earth's crust and is obtained chiefly from the mineral cassiterite, where it occurs as tin dioxide. (L307, L309)

이름 및 식별자

우선 이름
Butyltin trichloride
IUPAC
butyl(trichloro)stannane
현지명
뷰틸주석 트리염화물
영어명
Butyltin trichloride
분자식
C4H9Cl3Sn
분자량
282.18

이름 및 동의어

Butyltin trichloride1118-46-3ButyltrichlorostannaneStannane, butyltrichloro-N-Butyltin trichlorideButyltrichlorotinMONOBUTYLTIN TRICHLORIDETrichlorobutyltinTrichlorobutylstannaneStannane, trichlorobutyl-Monotributyltin trichlorideMono-n-butyltin trichloride
이름 더 보기
부틸주석트리염화물뷰틸주석트리염화물뷰틸주석트리염화물(BUTYLTINTRICHLORIDE)MBTCMBTCLbutylstanniumtrichloridemonotributyltintrichlorideBuSnCl3tin trichL
Chlorid n-butylcinicityButylstannium trichlorideDTXSID0029210Tin, n-butyl-, trichloride9R2DZM42GMDTXCID609210NSC-67013RefChem:122341

데이터베이스 식별자

CAS
1118-46-3
PubChem CID
14236
DTXSID
DTXSID0029210
EC Number
214-263-6

물성

구조 계산 물성보충 중

극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
2
무거운 원자 수
8
형식 전하
0
복잡도
58.8

실험 및 물리화학적 성질

Chemical ClassesMetals -> Tin Compounds, Organic
LogPlog Kow= 0.41
Density1.71 at 25 °C/4 °C
Color/FormColorless liquid
SolubilitySol in organic solvents; sparingly sol in water with partial hydrolysis
Flash Point81 °C (closed cup)
Boiling Point102 °C @ 12 mm Hg
DecompositionWhen heated to decomposition it emits toxic fumes of Cl- /chlorides/.
Melting Point-63 °C
Refractive Index · 2건

Index of refraction: 1.5190 at 25 °C

INDEX OF REFRACTION 1.5244 AT 20 °C

Physical Description · 2건

Liquid; Dry Powder

Colorless liquid; [HSDB] Yellow to red clear liquid; [MSDSonline]

Stability/Shelf Life

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 5% (6 of 120) of reports.

Danger

H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 120 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

유해성 정보

Regulatory Information · 4건

Chemical: Stannane, butyltrichloro-

Stannane, butyltrichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Stannane, butyltrichloro- 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: 07-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14718

Stannane, butyltrichloro-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Stannane, butyltrichloro-: Human health tier II assessment
Hazards Summary · 1건

A strong skin irritant Oral LD50 (rat) = 2140 mg/kg; [Sax] Corrosive to skin and eyes; [eChemPortal: ERMA] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; [MSDSonline] See Tin, organic compounds.

Toxic Combustion ProductsWhen heated to decomposition it emits toxic fumes of Cl- /chlorides/.

화학 및 산업

약리 정보

Mechanism of Action · 1건

The effects of dibutyltin and tributyltin compounds on the thymus were studied in relation to the cell kinetics of thymic atrophy. Male Wistar rats were exposed to single oral doses of 10 to 180 mg/kg mono-n-butyltin trichloride, 5 to 35 mg/kg di-n-butyltin dichloride, and 5 to 60 mg/kg tri-n-butyltin chloride. Body weights and organ weights for thymus, spleen, liver, kidneys, and adrenals were measured at varying times up to 9 days after exposure, and thymocyte suspensions were assessed for cell counts, cell size, and the incorporation of DNA, RNA, and protein precursors into acid precipitable material. Organ weights were not affected by any dose of mono-n-butyltin but were reduced di-n-butyltin dichloride and tri-n-butyltin chloride with the most significant effects obvious at 4 days post treatment. Dose levels reducing the relative thymic weight by 50% were 18 mg/kg di-n-butyltin dichloride and 29 mg/kg tri-n-butyltin chloride. Di-n-butyltin dichloride and tri-n-butyltin chloride produced a dose related reduction of cortical lymphocytes in thymus with pronounced reduction in the width of the thymic cortex at doses greater than 100 umol/kg body weight. The frequency of small cells in thymocyte suspensions increased over the 9 day post exposure period with progressive decrements in the number of intermediate and large thymocytes. Lymphoblast counts increased significantly on post exposure day four concomitant with maximal thymic atrophy. It was/ suggested that atrophy of the thymus and the subsequent immunosuppression are characteristics of diorganotin compounds.

Metabolism/Metabolites · 1건

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)

용도 및 제조

관련 반응

8건
반응 기록 만들기
HRID 46615 반응식
HRID 46615반응물로uspto-grants-1979_11
HRID 96347 반응식
HRID 96347반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 364244 반응식
HRID 364244반응물로uspto-grants-1986_08
HRID 569217 반응식
HRID 569217생성물로반응물로uspto-grants-1988_03
HRID 1155303 반응식
HRID 1155303반응물로uspto-grants-1981_11
HRID 1155304 반응식
HRID 1155304반응물로uspto-grants-1981_11
HRID 1452270 반응식
HRID 1452270반응물로uspto-grants-1997_02
HRID 2059327 반응식
HRID 2059327반응물로uspto-grants-1982_03

화합물 노트

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FUMES IN CONTACT WITH AIR

물리화학적 성질

녹는점
-63 °C · -63°C
끓는 점
93 °C/10 · 93 °C/10 mmHg (lit.)
밀도
1.693 g/mL · 1.693 g/mL at 25 °C (lit.)
증기압
11.1 Pa · 11.1Pa at 20℃
굴절률
20 · n20/D 1.523(lit.)
인화점
178 °F · 178 °F
용해도
1000 g/L · 1000g/L in organic solvents at 20 ℃
물리적 상태
액체
Specific Gravity
1.693 · 1.693
색상
무색~황색
수용성
녹는
안정성
흡습성, 수분 민감성
InChI
1S/C4H9.3ClH.Sn/c1-3-4-2;;;;/h1,3-4H2,2H3;3*1H;/q;;;;+3/p-3
InChIKey
YMLFYGFCXGNERH-UHFFFAOYSA-K
SMILES
CCCC[Sn](Cl)(Cl)Cl
LogP
1.145 · 1.145
NIST
n-Butyltin trichloride(1118-46-3)
EPA
Butyltin trichloride (1118-46-3)

화학적 성질

Clear yellow liquid

Hazard Classes and Categories · 4건

Acute Tox. 4 (40%)

Skin corrosion - category 1

Flammable liquids - Category 4

Flammable liquids - Category 4

State Drinking Water Guidelines(MN) MINNESOTA 4000 ug/l /Tin/
Shipping Name/ Number DOT/UN/NA/IMO · 3건

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

Skin, Eye, and Respiratory IrritationsSTRONG IRRITANT TO SKIN.

안전 및 보호

Exposure Control and Personal Protection0.02 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
Disposal Methods · 1건

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 · 5건

AVOID EXPOSURE TO LIQUIDS OR VAPORS.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. All contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Wherever possible, safer substitutes should be used in the place of alkyltin compounds. When it is necessary to make and use them ... /handling should be done in/ enclosed systems ... /equipped with/ exhaust ventilation. Engineering control should ensure that exposure limits are not exceeded. Personal protective equipment should be worn, & in appropriate circumstances respiratory protection should be used. Emergency showers should be installed ... to allow workers to wash immediately after splashes. /Organotin compounds/

SRP: The scientific literature supports the wearing of contact lenses in industrial environments, as part of a program to protect the eye against chemical compounds and minerals causing eye irritation. 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.

For more Preventive Measures (Complete) data for MONO-N-BUTYLTIN TRICHLORIDE (12 total), please visit the HSDB record page.

Threshold Limit Values (TLV) · 4건

0.1 [mg/m3], as Sn

0.2 [mg/m3], as Sn

8 hr Time Weighted Avg (TWA): 0.1 mg/cu m; 15 min Short Term Exposure Limit (STEL): 0.2 mg/cu m, skin. /Tin, organic cmpd, as Sn/

A4; Not classifiable as a human carcinogen. /Tin, organic cmpd, as Sn/

Permissible Exposure Limit (PEL)0.1 [mg/m3], as Sn
Personal Protective Equipment (PPE) · 5건

Safety goggles or face shields should be worn (8 inch minimum). Impervious clothing should include gloves, aprons, and suits. /Organotin compounds/

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... /Organotin compounds, NOS/

Recommendations for respirator selection: Max. concn for use: 1 mg/cu m). Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust and mist filter. Any supplied-air respirator. /Tin (organic cmpds, as Sn)/

Recommendations for respirator selection: Max. concn for use: 2.5 mg/cu m). Any supplied-air respirator operated in a continuous-flow mode. Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust and mist filter. /Tin (organic cmpds, as Sn)/

For more Personal Protective Equipment (PPE) (Complete) data for MONO-N-BUTYLTIN TRICHLORIDE (8 total), please visit the HSDB record page.

Immediately Dangerous to Life or Health (IDLH)25.0 [mg/m3], as Sn

독성 정보

Health EffectsBreathing 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)
Environmental Fate · 3건

Mono-n-butyltin trichloride is expected to dissociate in soil forming the cation, mono-n-butyltin(SRC). Mono-n-butyltin is expected to adsorb to organic carbon and clay; therefore, mobility in soil will be limited(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). The potential for volatilization of mono-n-butyltin trichloride from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 1.3 mm Hg(SRC), determined from a fragment constant method(1). In a 278-day marine mesocosm experiment in which tributyltin was added in summer, mono-n-butyltin was formed as a degradation product; there was no evidence that mono-n-butyltin degraded in water or sediment(2) and, therefore, mono-n-butyltin may be stable in soil(SRC).

AQUATIC FATE: Mono-n-butyltin chloride is expected to dissociate in water forming the cation, mono-n-butyltin(SRC). The hydrated mono-n-butyltin cation is acidic and forms hydroxylated mono-n-butyl cation species in solution(1). Cations generally adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). Butyltin compounds may react with sulfides present in sediment, leading to the formation of mono-n-butyltin sulfide(2). In a 278-day marine mesocosm experiment in which tributyltin was added in summer, mono-n-butyltin was formed as a degradation product but there was no evidence that mono-n-butyltin degraded in water or in sediment(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mono-n-butyltin trichloride, which has an estimated vapor pressure of 1.3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase mono-n-butyltin trichloride 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 1.1 days(SRC), calculated from its rate constant of 14X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Butyltin species obtained by dissolution of mono-n-butyltin trichloride in water weakly absorb light at wavelength >290 nm(4); therefore, mono-n-butyltin trichloride may be subject to direct photolysis(SRC). Mono-n-butyltin trichloride may dissociate in moist air which results in the formation of hydrogen chloride and hydrated butyltin hydroxide dichloride(5).

Food Survey ValuesIn a survey of Canadian wines from 3 provinces, monobutyltin was found in 10.8% of samples with levels ranging from 1.1-21.4 ng/ml. The sources of butyltin residues appeared to be the use of non-food grade PVC as liners in transport tanks.
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral (L308) ; inhalation (L308) ; dermal (L308)
Toxicity Summary · 1건

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 SymptomsInorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)
Effluent ConcentrationsThe concn of monobutyltin in the effluent of five municipal sewage treatment plants in Germany ranged from 9-19 ng Sn/l while that of a producer of organotin compounds was 2130 ng Sn/l(1).
Soil Adsorption/Mobility · 2건

The adsorption of butyltin trichloride was studied under simulated estuarine conditions which included artificial seawater (salinity (S)), hydrous iron oxide (modelling particulate matter (PM)) and fulvic acid(1). The partition coefficients Kp (ug/kg)/ug/l) ranged from 95,000 (at pH 7.2, moderate S and moderate PM concn) to 1X10+6 (at high PM concn at either pH 8.2 and high or low S or pH 6.2 and high S). Based upon these results, butyltin trichloride is expected to exist mainly in the adsorbed phase in estuarine and seawater(1). In a study of desorption from sediment, approximately 2% of the initial butyltin species was observed to desorb from the unshaken Toronto Harbor (Canada) sediment/water mixtures in 10.6 months(2).

Mono-n-butyltin trichloride is expected to dissociate in soil forming the cation, mono-n-butyltin, which is expect to adsorb strongly to soil(SRC). In a 278-day marine mesocosm experiment in which tributyltin was added to the system in summer, the distribution coefficient for mono-n-butyltin between dissolved state and particulate matter calculated from data between days 2-19 was 2900 L/kg (standard deviation 500). Other investigators obtained distribution constants for adsorption of mono-n-butyltin to particulate matter and sediment of 2,600 L/kg and 1800-29,000 L/kg, respectively; values were a function of sediment type and location(1). The Freundlich parameters, log k and 1/n, for mono-n-butyltin to sediment were 2.92 and 0.622, respectively(2).

Fish/Seafood Concentrations · 1건

The only monitoring data located were for monobutyltin (BuSn+++) without regard for the identity of the accompanying anion(s) and concn was reported in Sn equivalents(1). Monobutyltin was detected and quantified in 1 of 14 samples of whole fish collected from Canadian surface waters during 1982 and 1984 at the following concn (species; location): 0.06 ppm Sn (wet wt), herring (Clupea harengus pallasi; Vancouver Harbor); monobutyltin also was detected, not quantified in another 4 of the samples (concn <0.01 ppm Sn (wet wt) (limit of quantitation))(1). The levels of monobutyltin in mussel tissue (n=16) in the Sado Estuary, Portugal were 3.2-169 ng/g dry wt(2).

Artificial Pollution Sources · 1건

Mono-n-butyltin trichloride's production and use as an intermediate in the production of other mono-n-butyltin compounds, as a poly(vinyl chloride) stabilizer, and use in the hot-end coating of glass to improve abrasion resistance and bursting strength of glass bottles(1) may result in its release to the environment through various waste streams(SRC). Mono-n-butyltin is formed as a degradation product of tributyltin, an antifouling agent used in marine paint and dibutyltin(2).

Environmental Biodegradation · 1건

Tributyltin species, obtained by dissolution of tributyltin oxide in water, are sequentially degraded by microorganisms to dibutyltin, monobutyltin (similar to the monobutyltin obtained by dissolution of mono-n-butyltin trichloride), and finally to inorganic tin using water/sediment mixtures or water alone from Toronto Harbor, Canada(1). Butyltin compounds may be susceptible to biomethylation based upon the possible biomethylation of dibutyltin and tributyltin compounds(1).

규제 정보

State Drinking Water Guidelines(MN) MINNESOTA 4000 ug/l /Tin/

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
WH6780000
ridadr
UN 3265 8/PG 2
HS 번호
29319090
risk_code
20/21/22-34-20/21-50/53-37-20
hazard_code
C,N,Xn
safety_code
26-27-28-36/37/39-45-61-60
포장분류
II
위험 등급
6.1
기존화학 물질
KE-25487
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1BSTOT SE 3
스토리지 클래스
8A - Combustible corrosive hazardous materials
유해 물질 데이터
1118-46-3(Hazardous Substances Data)
Uses · 4건

A degradation product of dibutyltin and tributyltin (antifouling agents in marine paints); Used as an intermediate for other mono-n-butyltin compounds, a PVC stabilizer, and a hot-end coating of glass bottles; [HSDB]

Glass Manufacturing [Category: Industry]

Hot-end coating of glass to improve abrasion resistance and bursting strength of glass bottles.

Although generally less effective than dialkyl tin compounds as PVC stabilizers, monoalkyltin compounds when added to dialkyltin compounds in amounts of 5-20 wt% exert a synergistic effect on stabilizer effectiveness, preventing early yellowing.

U.S. Production · 2건

2023: 10,000,000 - <50,000,000 lb

(1977) AT LEAST 5.04X10+7 GRAMS

Consumer UsesIntermediate
Industry UsesIntermediate
Methods of Manufacturing · 2건

REDISTRIBUTION REACTION OF TETRA-N-BUTYLTIN & STANNIC CHLORIDE IN AN APPROX 1:3 RATIO TO FORM A MIXTURE OF CHLOROBUTYLTINS, FOLLOWED BY SEPN; OXIDATIVE ADDITION OF N-BUTYL CHLORIDE TO STANNOUS CHLORIDE IN THE PRESENCE OF TRI-N-BUTYLANTIMONY CATALYST.

The oxidative addition of aliphatic organic halides to stannous chloride has long been of interest for the preparation of monoorganotin trihalides. Fair to good yields are obtained for the reaction with quaternary ammonium or phosphonium catalysts. Trialkylantimony compounds at 100-160 °C are also used as catalyst.

General Manufacturing Information · 2건

Plastics Product Manufacturing

Stannane, butyltrichloro-: ACTIVE

응용 분야

용도Glass hot end spraying

상·하류 제품 정보

상류 원료

테트라부틸틴

하류 제품

2-(Bromomethyl)tetrahydro-2 H-pyran모노부틸 틴 옥사이드4-Butylbenzoic acid