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Tetrabutyltin

Tetrabutyltin structure

Tetrabutyltin 

structure
  • CAS No:

    1461-25-2

  • Formula:

    C16H36Sn

  • Chemical Name:

    Tetrabutyltin

  • Synonyms:

    Stannane,tetrabutyl-;Tetrabutylstannane;Tetra-n-butyltin;Tetrabutyltin;Tetra-n-butylstannane;Tetrabutyltin(IV);NSC 22330;NSC 28131;NSC 65524

  • Categories:

    Organic Chemistry  >  Organometallic Compounds

Description

Liquid


Liquid

Tetrabutyltin Basic Attributes

347.17

347.17

215-960-8

QJ7Y5V377V

65524|28131|22330

DTXSID4022153

Colorless or slightly yellow oily liquid

29310095

Characteristics

0

9.86

colorless liquid

1.054 g/cm3 @ Temp: 20 °C

-97 °C

145 °C @ Press: 10 Torr

225 °F

n20/D 1.473(lit.)

H2O: insoluble

Store below +30°C.

0.0048 mm Hg at 20 deg C

Oral-Mouse LD50: 6000 mg/kg

Distinct, characteristic odor

The most important reactions which tetraorganic tins undergo are heterolytic, i.e. electrophilic and nucleophilic, cleavage and the Kocheshkov redistribution. The tin-carbon bond in tetraorganic tins is easily cleaved by halogens, hydrogen halides, and mineral acids. /Tetraorganotins/

61.3 kJ/mol

Safety Information

III

6.1(b)

UN 1760 8/PG 2

3

21-25-36/38-48/23/25-50/53-48/23

35-36/37/39-45-60-61

WH8605000

T,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable. Incompatible with strong oxidizing agents. Combustible.

P273-P280-P301 + P310-P305 + P351 + P338-P314-P501

H301-H312-H315-H319-H372-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|H301 (74.58%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P284, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 59 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P260, P261, P264, P271, P281, P304+P340, P305+P351+P338, P308+P313, P312, P314, P337+P313, P403+P233, P405, and P501

Employees should be provided with & required to use impervious clothing, gloves, face shields (8 inch minimum), & other appropriate protective clothing necessary to prevent repeated or prolonged skin contact with ... solid or liquid tetrabutyltin. ... Employees should be provided with & required to use dust- & splash-proof safety goggles where ... liquid tetrabutyltin ... may contact the eyes.

Clothing contaminated with ... tetrabutyltin ... should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of contaminant from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the contaminant, the person performing the operation should be informed of contaminant's hazard properties. ... Non-impervious clothing which becomes contaminated with ... tetrabutyltin ... should be removed promptly & not reworn until the contaminant is removed. ...|Skin that becomes contaminated with ... tetrabutyltin ... should be promptly washed or showered with soap or mild detergent & water to remove any contaminant. ... Eating & smoking should not be permitted in areas where ... tetrabutyltin ... is handled, processed, or stored.|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.

SEDIMENT: Tetrabutyltin was detected and quantified in 1 of 235 samples of the top 2 cm of sediment from bodies of surface water in Canada sampled between 1982-1985 at concentration of 0.02 ppm Sn (dry wt); tetrabutyltin also was detected, not quantified in another 1 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).

Toxicity

practically nontoxic

LD50 Mouse intravenous 56 mg/kg|LD50 SWISS WEBSTER ALBINO MOUSE ORAL 6000 MG/KG|Irritant dose Rabbit ocular 500 mg/24 hr; irritant effects: mild eye irritation

Tetra-n-butyl tin's production and use as a rust inhibitor and chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 101,400(SRC), determined from a structure estimation method(2), indicates that tetra-n-butyl tin is expected to be immobile in soil(SRC). Volatilization of tetra-n-butyl tin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption may attenuate this process. Tetra-n-butyl tin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0048 mm Hg(4). Tetrabutyltin may be susceptible to biodegradation in soil based upon possible biodegradability of other butyltin compounds such as tri-, di- and monobutyltin species(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 101,400(SRC), determined from a structure estimation method(2), indicates that tetra-n-butyl tin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hrs and 7 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 2.5 yrs if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 100(SRC), from an estimated log Kow of 9.4(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Tetrabutyltin may be susceptible to biodegradation in water based upon possible biodegradability of other butyltin compounds such as tri-, di- and monobutyltin species(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetra-n-butyl tin, which has a vapor pressure of 0.0048 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tetra-n-butyl tin 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 7 hrs(SRC), calculated from its rate constant of 5.69X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). It may be susceptible to direct photolysis based upon the absorption of UV light >290 nm by tri-, di-, and monobutyltin compounds(4), and should react with photochemically produced hydroxyl radicals.

The rate constant for the vapor-phase reaction of tetra-n-butyl tin with photochemically-produced hydroxyl radicals has been estimated as 5.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tetra-n-butyl tin is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). It may be susceptible to direct photolysis based upon the absorption of UV light >290 nm by tri-, di-, and monobutyltin compounds(3), and should react with photochemically produced hydroxyl radicals(SRC). Tetra-n-butyltin may react with free radicals since the Sn-C bond is a good radical trap(2).

An estimated BCF of 100 was calculated for tetra-n-butyl tin(SRC), using an estimated log Kow of 9.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tetra-n-butyl tin can be estimated to be 101,400(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetra-n-butyl tin is expected to be immobile in soil.

The Henry's Law constant for tetra-n-butyl tin is estimated as 6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tetra-n-butyl tin is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 7 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 2.5 yrs if adsorption is considered(3). Tetra-n-butyl tin's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC); however, adsorption will attenuate this process. Tetra-n-butyl tin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.8X10-3 mm Hg(4).

SURFACE WATER: Tetrabutyltin was detected and quantified in 2 of 214 samples of unfiltered subsurface water from 209 locations in Canada sampled between 1982-1985 at concentrations of 0.12 and 0.02 ppb Sn; tetrabutyltin also was detected, not quantified in another 1 of the samples (concn range from approx 3.3 parts/trillion Sn (limit of detection) to <0.01 ppb Sn (limit of quantitation))(1). Tetrabutyltin was not detected in samples from six sites in New York state and one in Michigan(1). Analysis for tetrabutyltin in samples of unfiltered surface microlayer and subsurface water from Maryland waters of Chesapeake Bay sampled approx monthly between July 1985 to June 1986, gave the following results: four marinas, microlayer, 4 of 44 samples pos, 0.061 to 0.41 ppb, 0.192 ppb avg; subsurface, not detected in 48 samples; Baltimore Harbor, microlayer, 1 of 6 samples pos, 0.108 ppb; subsurface, 2 of 12 pos, 0.034 to 0.038 ppb; Chesapeake and Delaware Canal (a major shipping canal), microlayer, 1 of 6 samples pos, 0.526 ppb; subsurface, not detected in 12 samples; Potomac and Choptank Rivers, microlayer not detected in 11 samples; subsurface, not detected in 24 samples(2).

Occupational exposure to tetra-n-butyl tin may occur through dermal contact with this compound at workplaces where tetra-n-butyl tin is produced or used. Monitoring data indicate that the general population may be exposed to tetra-n-butyl tin via ingestion of contaminated water and dermal contact with consumer products containing tetra-n-butyl tin. (SRC)

Drug Information

Butyltin compounds inhibited the activity of purified yeast glucose-6-phosphate dehydrogenase in an in vitro system. The order of inhibitory effect was tetrabutyltin, dibutyltin, tributyltin and monobutyltin. The concentration of tetrabutyltin giving 50% inhibition of the yeast enzyme was 4.3ited by tributyltin but not by monobutyltin, dibutyltin or tetrabutyltin. Inhibition of glucose-6-phosphate dehydrogenase of yeast by tributyltin and tetrabutyltin was prevented by the addition of bovine serum albumin; inhibition of activity of the erythrocyte enzyme by tributyltin was not affected. Addition of albumin to the once inactivated enzyme did not restore enzyme activity. Cysteine slightly protected yeast enzyme from inhibition by dibutyltin but did not affect inhibition by tributyltin and tetrabutyltin.

tetrabutylstannane

Tetrabutyltin Use and Manufacturing

Methods of Manufacturing

Reaction of tin tetrachloride with butyl magnesium chloride.|From activated magnesium chips, butyl chloride, and stannic chloride in a hydrocarbon mixture.|REACTION OF STANNIC CHLORIDE AND TRI-N-BUTYLALUMINUM IN THE PRESENCE OF COMPLEXING AGENTS SUCH AS SODIUM CHLORIDE, ETHERS, OR TERTIARY AMINES; REACTION OF STANNIC CHLORIDE AND N-BUTYLMAGNESIUM CHLORIDE; REACTION OF STANNIC CHLORIDE AND N-BUTYL CHLORIDE|Commercial mfr of organotins traditionally has involved alkylation of tin tetrachloride or the direct reaction of tin with alkyl halides. /Organotin cmpd/

Uses

Tetrabutylstannane, which is used in hydrogenolysis reactions and as a transition metal catalyst.


Intermediates

Production

1,000,000 - 10,000,000 lb

All other chemical product and preparation manufacturing|Stannane, tetrabutyl-: ACTIVE|Organotin stabilizers are all derivatives of tetravalent tin. ... The organic groups bonded to tin are either alkyl or, substituted alkyl. Aryltin compounds have been shown to be poor stabilizers for polyvinyl chloride. /Organotin cmpd/|Among the most widely used preparations of tetraalkyl- and tetraaryltin compounds is the reaction of stannic chloride with tetrahydrofuran-based Grignard reagents or organoaluminum compounds. ... Organolithium and organosodium reagents can also be used to prepare tetraorganotins. ... The Wurtz reaction, which relies on in situ formation of an active organosodium species, is also useful for preparing tetraorganotin compounds and is practiced commercially. ... Unsymmetrical functional tetraorganotins are generally prepared by tin hydride addition (hydrostannation) to functional unsaturated organic compounds. /Tetraorganotin compounds/|COMMERCIAL ORGANOTIN COMPOUNDS USED AS STABILIZERS ARE OFTEN NOT CLEARLY IDENTIFIED AS TO THE EXACT ORGANOTIN, NOR IS INFORMATION GIVEN AS TO THE PRESENCE OF OTHER INGREDIENTS. ... /ORGANOTIN COMPOUNDS/

NIOSH Method 5504. Analyte: tetrabutyltin. Matrix: Air. Procedure: Atomic absorption, graphite furnace. For tetrabutyltin this method has an estimated detection limit of 1 ug tin per 300 liter sample. The overall precision/RSD is 10.0%. Applicability: The working range is 0.015 to 1 mg/cu m (as tin) for a 300 liter air sample. Interferences: Organotin compounds not separated chromatographically will mutually interfere.

Computed Properties

Molecular Weight:347.2
Rotatable Bond Count:12
Exact Mass:348.183904
Monoisotopic Mass:348.183904
Heavy Atom Count:17
Complexity:116
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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