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).

REFERENCE

Metody elementoorganicheskoi khimii. Moscow, 1968.

D. N. KRAVTSOV

References in periodicals archive ?
haemastoma developed imposex characteristics when ingesting food sources contaminated with organotin compounds (Lima et al., 2006).
Organotin compounds promote adipocyte differentiation as agonists of the peroxisome proliferator-activated receptor gamma/retinoidx receptor pathway.
Ligand also plays an important role in determining the degree of activity of organotin compounds [48].
This study analyzed the interaction between the novel patent organotin compound DBDF2,6T and the hPPAR[gamma] protein under physiological condition with the methods of fluorescence quenching, 3D fluorescence, DARTS, ultrafiltration-LC, and computer molecular docking.
Wang, "Speciation analysis of organotin compounds in sediment by hyphenated technique of high performance liquid chromatography-inductively coupled plasma mass spectrometry," Chinese Journal of Analytical Chemistry, vol.
Further, concentrations of organotin compounds are high in ports and shipyards.
Occurrence of imposex in Thais haemastoma: possible evidence of environmental contamination derived from organotin compounds in Rio de Janeiro and Fortaleza, Brazil.
caused by organotin compounds used in anti-fouling systems." (45)
Fernandez, "Cymatium parthenopeum parthenopeum (von Salis, 1793) (Caenogastropoda: Ranellidae): a new bioindicator of organotin compounds contamination?" Journal of the Brazilian Society of Ecotoxicology, vol.
The mechanism of the neurotoxicity and underlying selective vulnerability of trimethyltin have not been fully elucidated it has been proposed that mitochondrial targeting of the organotin compounds leads to a change in local microenvironment in which TMT interacts with the protein Stannin, compromising the integrity of the mitochondrial membrane and initiating apoptosis (Billingsley et at.
This study also aims to evaluate the sorption abilities by mesoporous silica grafted with calix[4]arene derivatives toward some selected organotin compounds. We have performed several solid-liquid sorption studies of organotins compounds (Tributyltin TBT, Triphenyltin TPT, and Dibutyltin DBT) by using MCM-PS TDI-calix[4]arene derivatives as sorbents.
For PubMed search, we used ("endocrine disruptors" [MeSH] OR "endocrine disrupting chemicals" OR "obesogen" [mh] OR "Polychlorinated Biphenyls" [MeSH] OR "Hydrocarbons, Chlorinated" [MeSH] OR "Dioxins" [MeSH] OR "Polybrominated Biphenyls" [MeSH] OR "Carbon Tetrachloride" [MeSH] OR "Organothiophosphorus Compounds" [MeSH] OR "phthalic acid" [Substance Name] OR "Phthalic Acids" [MeSH] OR "Organotin Compounds" [MeSH] OR "bisphenol A" [Substance Name] AND (("obesity" [mh] OR "overweight" [mh] OR "excess weight" [mh] OR "body mass index" [mh] OR "weight gain" [mh] OR "adipogenesis" [mh] OR "adipose tissue" [mh] OR "fat deposition" [mh]) AND (publisher[sb] OR "in process" [sb]).