General Description
Odorless white powder. Stable at room temperature. Melting point 121-123°C. Moderately soluble in most organic solvents (Farm Chemical Handbook). Insoluble in water. Non corrosive. Used as a fungicide.
Reactivity Profile
TRIPHENYLTIN HYDROXIDE(76-87-9) is sensitive to temperatures above 113°F and prolonged exposure to light. Incompatible with strongly acidic compounds. Also incompatible with oils used in oil spray formulations .
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available; however, TRIPHENYLTIN HYDROXIDE is probably combustible.
Description
Fentin hydroxide is an obsolete organotin fungicide. It has a low aqueous solubility and low volatility. Evidence suggests it is not persistent in soil systems but may be more so in aquatic systems. Based on its physico-chemical properties it is not expected to leach to groundwater. Ecotoxicological data is limited but acute oral ecotoxicity tends to be high to moderate. It is moderately toxic to mammals via the oral route.
Chemical Properties
White to Off-White Solid. Insoluble in water; soluble in ether, benzene, and alcohol.
Uses
Reactant involved in transmetalation reactions with Ir clusters. Reactant involved in synthesis of (E)-(Nitrophenyl)propenoic acid organotin(IV) carboxylates with antitumor activity, triorganotin chrysanthemumates for larvicidal studies, polynuclear organotin(IV) carboxylates containing ferrocenyl moieties for antitumor investigation, organotin(IV) aminophenylacrylate complexes, 4-Biphenylcarboxylic acid derivatives for in vitro cytotoxicity studies.
Uses
Triphenyltin Hydroxide is an organotin compound. Triphenyltin Hydroxide is used as a fungicide and antifeeding compound for insect control. Recent studies show that Triphenyltin Hydroxide may have adv
erse effects on the reproductive and immune systems and may disrupt the endocrine system.
Definition
ChEBI: An organotin compound that is triphenylstannane in which the hydrogen attached to tin is replaced by a hydroxy group. A fungicide used to control a variety of infections including blight on potatoes, leaf spot on sugar beet and alternaria blight on carrots
Production Methods
Fentin hydroxide is commercially produced by hydrolysing triphenyltin chloride in an aqueous medium. The process begins with the reaction of triphenyltin chloride with water or a dilute base such as sodium hydroxide, which facilitates the substitution of the chloride ion with a hydroxyl group to form triphenyltin hydroxide. This reaction is typically carried out under controlled temperature and pH conditions to ensure complete conversion and minimize side reactions.
Biochem/physiol Actions
Keratin 19 (KRT19) is a type I cytokeratin involved in the formation of intermediate filaments in other cells. It is also involved in the myofiber organization. It is localized at the costameres of striated muscle. KRT19 serves as a connector between contractile apparatus and dystrophin at the costamere of striated muscle. It has been postulated that KRT19 can bind directly with the N-terminal actin-binding domain of dystrophin, neurofilaments, vimentin and plectin. It also functions as a biomarker for the diagnosis of endometriosis.
Mechanism of action
Curative and protective action. Inhibitor of mitochondrial ATP synthase.
Purification Methods
West, Baney and Powell [J Am Chem Soc 82 6269 1960] purified a sample which was grossly contaminated with tetraphenyltin and diphenyltin oxide by dissolving it in EtOH, most of the impurities remaining behind as an insoluble residue. Evaporation of the EtOH extract gave the crude hydroxide which was converted to triphenyltin chloride (above) by grinding in a mortar under 12M HCl, then evaporating the acidic solution. The chloride, after crystallisation from EtOH, had m 104-105o. It was dissolved in Et2O and converted to the hydroxide by stirring with excess aqueous ammonia. The ether layer was separated, dried, and evaporated to give triphenyltin hydroxide which, after crystallisation from EtOH (or MeCN) and drying under vacuum, was in the form of white crystals (m 119-120o), which retained some cloudiness in the melt above 120o. The hydroxide retains water (0.1-0.5 moles of water per mole) tenaciously. [Glidewell & Liles Acta Cryst (B) 34 129 1978, Beilstein 16 H 914, 16 I 540, 16 II 625, 16 III 1240, 16 IV 1606.]
