Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Butyltin trichloride

Butyltin trichloride

Butyltin trichloride structure

Butyltin trichloride 

structure
  • CAS No:

    1118-46-3

  • Formula:

    C4H9Cl3Sn

  • Chemical Name:

    Butyltin trichloride

  • Synonyms:

    Stannane,butyltrichloro-;Butyltin trichloride;Butyltrichlorostannane;Monobutyltin trichloride;Trichlorobutyltin;Butyltrichlorotin;Trichlorobutylstannane;Butyltin trichloride (BuSnCl3);n-Butyltin trichloride;Certincoat TC 100;NSC 67013;2243499-55-8

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Clear yellow liquid


Liquid

Butyltin trichloride Basic Attributes

282.18

282.18

214-263-6

67013

DTXSID0029210

Colorless liquid

29319090

Characteristics

0

0.41

colorless to yellow liquid

1.71 g/cm3 @ Temp: 25 °C

-63 °C

102 °C @ Press: 12 Torr

178 °F

n 20/D 1.523(lit.)

Sol in organic solvents; sparingly sol in water with partial hydrolysis

Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Keep under a nitrogen blanket. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area. Store protected

0.12mmHg at 25°C

Oral-rat LD50: 2140 mg/kg

Thermal decomposition to emit toxic chloride fumes

Safety Information

II

6.1

UN 3265 8/PG 2

1

20/21/22-34-20/21-50/53-37-20

26-27-28-36/37/39-45-61-60

WH6780000

C,N,Xn

Warehouse ventilated, low temperature and dry

FUMES IN CONTACT WITH AIR

P261-P273-P280-P305 + P351 + P338-P310-P501

H314-H332-H335-H410

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.

|Danger|H302 (42.73%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P330, P332+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 116 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P321, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Warning|P210, P280, P370+P378, P403+P235, and P501

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.

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.

STRONG IRRITANT TO SKIN.

The 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).

SEDIMENT: 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 47 of 235 samples of the top 2 cm of sediment from bodies of surface water in Canada sampled between 1982-1985 at concentrations ranging from 0.01 to 4.73 ppm Sn (dry wt) (avg concn of positive, quantified samples = 0.34 ppm Sn (dry wt)); monobutyltin also was detected, not quantified in another 27 of the samples (concn range from approx >3.3 ppb Sn (dry wt) (limit of detection) to <0.01 ppm Sn (dry wt) (limit of quantitation))(1). Monobutyltin was not detected in sediment from one site in Michigan and six sites in New York state(1).|SEDIMENT: The concn of monobutyltin species in sediment (upper 2 cm) from Toronto Harbor (4 sites) was trace-0.08 mg Sn/kg dry weight(1). The concn of monobutyltin in sediment from two harbors along the Rhine River in Germany were 27 and 34 ng Sn/g dry wt(2). Sediment from a tributary of the Rhine with a high input of sewage contained 547 ng Sn/g dry wt(2). Intertidal sediments at a restricted site downstream from the shipyards in the Sado estuary, Portugal reached levels of 2100 ng/g dry wt for monobutyltin, over an order of a magnitude higher than samples taken in March(3). This has been ascribed to the cleaning of ships in spring and points up the large seasonal variability in anthropgenic organotin levels. Fluvial, intertidal, and marine levels of monobutyltin at other sites in the Sado Estuary were 5.5-20, 5.5-181, and 6.3-14 ng/g.

Toxicity

moderately toxic

LD50 White mouse oral 1400 mg/kg|LD50 Rat oral 2140 mg/kg

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).

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).

The rate constant for the vapor-phase reaction of mono-n-butyltin trichloride with photochemically-produced hydroxyl radicals has been estimated as 14X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Butyltin compounds may react with sulfides present in sediment, leading to the formation of dibutyltin sulfide(2). The butyltin species obtained by dissolution of mono-n-butyltin trichloride in water weakly absorb light at wavelength >290 nm(3); therefore, these butyltin species may be subject to direct photolysis in sunlit waters(SRC). Mono-n-butyltin trichloride is susceptible to hydrolysis in moist air(4,5) which results in the formation of hydrogen chloride(5) and hydrated butyltin hydroxide dichloride(4). Water solutions of the compound are very acidic due to the formation of hydronium ion and presumably butyltin species with a certain number of coordinated hydroxide ions either in addition to or replacing the chlorides(4). In seawater, the chloride ion may compete effectively with hydroxide ions and stabilize the presence of mono-n-butyltin trichloride in solution(2).

An estimated BCF of 3 was calculated for mono-n-butyltin trichloride(SRC), using a log Kow of 0.41(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). Bioconcentration studies on compounds which are structurally similar, such as dibutyltin, also do not bioconcentrate to a great extent(4).

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).

Mono-n-butyltin trichloride is expected to dissociate in water forming the cation, monobutyltin(SRC). Volatilization from moist soil and water 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).

SURFACE WATER: The only monitoring data located were for monobutyltin (BuSn+++) without regard for the identity of the accompanying anion(s) and the concentration was reported in Sn equivalents(1). Monobutyltin was detected and quantified in 31 of 214 samples of unfiltered subsurface water from 209 locations in Canada sampled between 1982-1985 at concentrations ranging from 0.01 to 1.89 ppb Sn (avg concentration of positive, quantified samples = 0.18 ppb Sn); monobutyltin also was detected, not quantified in another 18 of the samples (concentration range from approx 3.3 parts/trillion Sn (limit of detection) to <0.01 ppb Sn (limit of quantitation))(1). Monobutyltin was detected at 0.01 ppb Sn at the one site sampled in the Detroit River, MI, and in two of six sites in New York state at 0.02 and 1.82 ppb Sn(1).|SURFACE WATER: The concentration of monobutyltin species in unfiltered subsurface water from Toronto Harbor (6 sites) ranged from a trace to 0.09 ug Sn/l(1). Monobutyl tin was found in unfiltered subsurface water from a marina on Lake St. Clair and Hamilton Harbor in Ontario at 8.48 and 0.02 ug/l, respectively(2). Detectable levels (>1 picomolar) of monobutyltin were found in three of the six estuaries studied: the Delaware, the Tamar in southwest England, and the Tejo in Portugal; monobutyltin is believed to come from the degradation of tributyltin which is used as in marine antifouling paint(4). Water samples taken over several months in the Rhine River at Mainz in 1989 reported monobutyltin levels of 0.7-2.3 ng Sn/l; monobutyltin was found in all 14 samples taken(3). In 4 harbors at Mainz and Wiesbaden, they ranged from 0.9-6 ng Sn/l. In the Schwarzbach, a tributary of the Rhine near Mainz, monobutyltin levels were 7 ng Sn/l, only slightly lower than that in the effluent of sewage treatment plants(3). This is consistent with the very high input of sewage in this stream. Monobutyltin concns ranged from <1-12.6 ng Sn/l, median <1 ng Sn/l in Sarah Creek (8 locations) but was not detected in the Elizabeth River (10 locations), both rivers feeding into the lower Chesapeake Bay(5).|SURFACE WATER: The only monitoring data located were for monobutyltin (BuSn+++) without regard for the identity of the accompanying anion(s)(1). Monobutyltin was detected in unfiltered surface and bottom water from San Diego Harbor in 25 of 32 samples taken in 1983 through 1985 from 5 stations at concn ranging from 0.01 to 0.12 ppb (0.04 avg concn)(1).

In 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.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1821 are potentially exposed to mono-n-butyltin trichloride in the USA(1). Occupational exposure to mono-n-butyltin trichloride may occur through inhalation and dermal contact with this compound at workplaces where mono-n-butyltin trichloride is produced or used(SRC).

Drug Information

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.

butyltin trichloride

Butyltin trichloride Use and Manufacturing

Methods of Manufacturing

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.

Uses

Glass hot end spraying


Intermediates


Paints and coatings

Production

10,000,000 - 50,000,000 lb|(1977) AT LEAST 5.04X10+7 GRAMS

All other chemical product and preparation manufacturing|Stannane, butyltrichloro-: ACTIVE

Computed Properties

Molecular Weight:282.2
Rotatable Bond Count:2
Exact Mass:281.879186
Monoisotopic Mass:281.879186
Heavy Atom Count:8
Complexity:58.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Downstream Products

Recommended Suppliers of Butyltin trichloride

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.