Tributyl tin chloride

Structural formula
General
Surname	Tributyl tin chloride
other names	Tributylchlorostannane; Tri- n -butyltin monochloride; TBTC; TBTCl;
Molecular formula	C 12 H 27 ClSn
Brief description	colorless to yellowish liquid
External identifiers / databases
EC number	215-958-7
ECHA InfoCard	100.014.508
PubChem	15096
ChemSpider	14368
Wikidata	Q2452578
properties
Molar mass	325.49 g mol −1
Physical state	liquid
density	1.20 g cm −3 (20 ° C)
Melting point	−9 ° C
boiling point	140 ° C (at 13 m bar )
solubility	almost insoluble in water (17 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 301-312-315-317-319-360FD-372-410
	P: 201-273-280-302 + 352-305 + 351 + 338-308 + 310
Toxicological data	147 mg kg −1 ( LD 50 , hamster , oral ) ; 60 mg kg −1 ( LD 50 , mouse , oral ) ; 129 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tributyltin chloride ( TBTC for short ) is an organometallic compound of tin . At room temperature, TBTC is a colorless to yellowish, almost water-insoluble, toxic liquid. The toxic effect is based on the inhibition of V-ATPases by organotin compounds .

presentation

To represent are tin tetrachloride SnCl ₄ and tri- n -butylaluminium nBu ₃ Al reacted:

{\ displaystyle \ mathrm {SnCl_ {4} + \ nBu_ {3} Al \ longrightarrow \ nBu_ {3} SnCl + \ AlCl_ {3}}}

By partial hydrolysis with water and a base such as pyridine or triethylamine , bis (tributyltin) oxide can be produced from the tributyltin chloride .

properties

TBTC is a colorless liquid, often yellowish in color due to impurities, that dissolves only slightly (17 mg · l ⁻¹ at 20 ° C) in water. The compound is largely stable to hydrolytic and oxidative influences. It has a dipole moment of 3.31 Debye in benzene .

use

Tributyltin compounds such as TBTC, tributyltin hydride (TBT) and bis (tributyltin) oxide (TBTO) and other organotin compounds are used as disinfectants against infestation with fungi and mites in textiles, leather, paper and wood and as seed dressings. They are also added to the paintwork of ships to combat algae and snails in anti- fouling colors . In Germany and the EU , the use of organotin compounds is largely avoided. In some cases, a usage ban applies.

Other important uses are in syntheses in pharmaceutical chemistry and as an additive to styrene-butadiene rubber to reduce the frictional resistance of car tires. In both cases, no organotin compounds enter the environment, which is why their use remains permitted.

toxicology

Because of the low vapor pressure of the liquid, uptake via the airways is unlikely; however, dermal and oral absorption is high. The toxicity to mammals is LD ₅₀ (oral - rat) = 220 mg · kg ⁻¹ . The substance has a strong irritant to corrosive effect on mucous membranes and skin and, in animal experiments, produced necrosis , reduced body weight, dampening of reflexes, exhaustion and cramps. Tributyltin chloride has a very high toxicity on aquatic life. Tin organics cause the Imposex phenomenon in snails , with the purple snail ( haustellum brandaris ) already showing effects from a concentration of 1.2 ng / l.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tributyltin chloride in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

↑ Not explicitly listed in Regulation (EC) No. 1272/2008 (CLP) , but with the specified labeling it falls under the group entry tributyltin compounds, unless specifically listed in this appendix in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2017. Manufacturers or distributors can extend the harmonized classification and labeling .

↑ Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 46, Pg. 297, 1991.

↑ ^a ^b ^c Entry on Tributylchlorostannane in the ChemIDplus database of the United States National Library of Medicine (NLM)

↑ Yakkyoku. Pharmacy. Vol. 30, Pg. 505, 1979.

↑ Prehled Prumyslove Toxicology; Organicke Latky. Marhold, J., Prague, Czechoslovakia, Avicenum, Pg. 1250, 1986.

↑ Wissenschaft-Online-Lexika: Entry on V-ATPases in the Lexicon of Biochemistry. Retrieved September 15, 2009

↑ Jörg Lorberth, Heinrich Nöth: Dipole moments of some organotin chlorides . In: Chemical Reports . tape 98 , no. 3 , March 1965, p. 969 , doi : 10.1002 / cber.19650980342 .

↑ Enius.de Pollutant Information Tributyltin Chloride

↑ ^a ^b Dietrich Klingmüller, Burkard Watermann (ed.): TBT - organotin compounds - a scientific inventory (PDF; 2.1 MB) . Federal Environment Agency Berlin, March 2003, ISSN 0722-186X

^ Bernard Jousseaume: Organometallic Synthesis and Chemistry of Tin and Lead Compounds . In: Mikrochimica acta . tape 109 , no. 1-4 , 1992, pp. 5–12 , doi : 10.1007 / BF01243203 (English).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tributyltin chloride in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[CLP_100.240.777-2] Not explicitly listed in Regulation (EC) No. 1272/2008 (CLP) , but with the specified labeling it falls under the group entry tributyltin compounds, unless specifically listed in this appendix in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2017. Manufacturers or distributors can extend the harmonized classification and labeling .

[3] Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 46, Pg. 297, 1991.

[chemid-4] Entry on Tributylchlorostannane in the ChemIDplus database of the United States National Library of Medicine (NLM)

[5] Yakkyoku. Pharmacy. Vol. 30, Pg. 505, 1979.

[6] Prehled Prumyslove Toxicology; Organicke Latky. Marhold, J., Prague, Czechoslovakia, Avicenum, Pg. 1250, 1986.

[7] Wissenschaft-Online-Lexika: Entry on V-ATPases in the Lexicon of Biochemistry. Retrieved September 15, 2009

[ChemBer1965_969-8] Jörg Lorberth, Heinrich Nöth: Dipole moments of some organotin chlorides . In: Chemical Reports . tape 98 , no. 3 , March 1965, p. 969 , doi : 10.1002 / cber.19650980342 .