Organotin Compounds


Also found in: Dictionary, Medical.

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).

REFERENCE

Metody elementoorganicheskoi khimii. Moscow, 1968.

D. N. KRAVTSOV

References in periodicals archive ?
Ligand also plays an important role in determining the degree of activity of organotin compounds [48].
Toxicity of dibutyltin, tributyltin and other organotin compounds to humans and to experimental animals.
In this area, surface waters are contaminated with mono- and dibasic phenols, pentachlorophenol, polycyclic aromatic hydrocarbons, organotin compounds, and phthalates.
Occurrence of imposex in Thais haemastoma: possible evidence of environmental contamination derived from organotin compounds in Rio de Janeiro and Fortaleza, Brazil.
containing organotin compounds were either removed or coated with a
Apoptosis of cerebellar granule cells induced by organotin compounds found in drinking water: involvement of MAP kinases.
Imposex is known to be induced by organotin compounds and it has been proved by both laboratory and field experiments (Bryan et al.
2008), and consequently to greater environmental contamination by organotin compounds.
A few representative examples of specific topics include spectroscopy of tin, macrocyclic and supramolecular chemistry of organotin compounds, unusual bonds and coordination geometries, tin compounds for chemical vapor deposition, tin compounds as flame retardants and smoke suppressants, quadratic non-linear optical properties of tin-based coordination compounds, the cardiovascular activity of organotin compounds, chemical and biotechnological developments in organotin cancer chemotherapy, applications of organotin derivatives for carbohydrate synthesis, and organotin catalysts for isocyanate reactions.
Basically, organotin compounds are characterized by a tin-carbon bond having arlyl or aryl groups; the organotin moiety is significantly toxic while anionic legend that influences physiological properties, is generally little or no toxic.
Moreover, tests have shown that exposure to certain commonly-used chemical substances (alkylphenols, phthalates, brominated flame retardants, organotin compounds, bisphenol-A, artificial musks, etc.
Brominated flame retardants, which are thought to interfere with the hormone systems vital to growth, and organotin compounds, considered harmful to the immune system, were also found in every sample.