Organotin Compounds

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Organotin Compounds


a class of organometallic compounds containing at least one C—Sn bond per molecule. Almost all known organotin compounds are formed from tetravalent tin; they include fully substituted R4Sn compounds, as well as compounds of the formulas R3SnX, R2SnX2, and RSnX3, where R represents identical or different organic radicals and X denotes a halogen, hydrogen, oxygen, or a radical bonded to the tin atom by a heteroatom of oxygen, nitrogen, sulfur, and so on: for example,—OCH3,—NHCH3,—OH, and—SR. Thus, the main organotin compounds containing oxygen are hydroxides, R3SnOH; oxides, R3SnOSnR3 and R2SnO; and stannous acids, RSnOOH. The molecules of certain organotin compounds form linear chains or rings of tin atoms containing side organic radicals.

Most organotin compounds have low-polarity Sn—C and Sn—X bonds. The Sn—C bond is less reactive than the tinheteroatom bond; it is resistant to the effects of water and atmospheric oxygen but breaks upon action of halogens and acids. A characteristic feature of organotin hydrides, RnSnH4 – n, is the ability to join to various multiple bonds. The physical properties of organotin compounds vary considerably, ranging from highly volatile liquids that are readily soluble in organic solvents to infusible and insoluble substances. Organotin compounds containing heteroatoms are often associated in solutions and crystals or exhibit polymeric structure.

Compounds of the R4Sn type are usually produced upon interaction of stannic chloride with organic compounds of lithium, magnesium, or aluminum, as well as by treating tin alloys containing sodium or magnesium with alkyl halides. Organotin halides are the starting materials for the preparation of various organotin compounds, which are formed by reaction of R4Sn with tin halides or with halogens or reaction of metallic tin with alkyl halides. Certain organotin compounds are toxic.

Compounds of the formulas R3SnX and R2SnX2 are widely used as stabilizers for polyvinyl chloride resins (for example, dibutyltin dilaurate), fungicides (triphenyltin acetate), and bactericides (tributyltin benzoate).


Metody elementoorganicheskoi khimii. Moscow, 1968.


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Although genetics, diet, and exercise all contribute to obesity, recent studies have shown that prenatal exposures to "environmental obesogens," including bisphenol A, phthalates, organotins, and perflourinated compounds may increase the risk of obesity in children (Janesick and Blumberg 2011).
Organotin heat stabilizers for rigid vinyl include Advastab TM-181 high-performance tin stabilizer for siding, profiles, injection and blow molding; TM-694 tin stabilizer for pipe; TM-280SP series for profile; TM-281IM for injection molding; and TM-948 for general-purpose bottles.
Organotin containing compounds are screened as potential anticancer agents and shows different mechanisms at the molecular level [12].
Using probabilistic modeling to evaluate human exposure to organotin in drinking water transported by polyvinyl chloride pipe.
High-efficiency barium/cadmium powders with improved early color for outdoor use; organotins for general-purpose bottles; and calcium/zinc and calcium/stannous/ zinc powders and pastes for food-contact use.
The lead and the cadmium, the organotin compounds are used as stabilisers in PVC products to prevent deterioration as a result of heat and light.
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The Council took note of an intervention by the Austrian delegation expressing its concern over findings in recent studies of traces of organotin compounds, particularly tributyltin (TBT) in babies' nappies and calling for the substance to be banned from all products with which human beings come into direct or indirect contact.
Considerable attention has been paid to organotin complexes in recent years, owing to their wide applications in various fields like catalysis, biotechnology, analytical and medicinal chemistry [1-5].