Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. An organotin compound is commercially applied as a hydrochloric acidscavenger (or heat stabilizer) in polyvinyl chloride and as a biocide. Tributyltin oxide (or tributyltin for short) has been extensively used as a wood preservative. Tributyltin compounds are used as marine anti-biofouling agents. Concerns over toxicity of these compounds (some reports describe biological effects to marine life at a concentration of 1 nanogram per liter) have led to a world-wide ban by the International Maritime Organization. n-Butyltin trichloride is used in the production of tin oxide layers on glass bottles by chemical vapor deposition.
A Grignard reagent is prepared from magnesium turnings and (Z)-2-bromo-5-phenyl-2-pentene in dry tetrahydrofuran and titrated with tributyltin chloride until the solution decolourises. The resulting solution is stirred at room temperature for 1 hour and the solvent is removed in a rotavapor. Diethyl ether is added and the ether extract is washed with brine and filtered and the ether evaporates in a rotavapor. The crude product is kugelrohr distilled to yield tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane as a colourless oil.
Tetraorganotins are very stable molecules with low toxicity and low biological activity. They are unusable as biocides, but they can be metabolized to toxic triorganotin compounds. They are used as starting materials for catalysts.
Triorganotins are very toxic. Tri-n-alkyltins are phytotoxic and therefore cannot be used in agriculture. Depending on the organic groups, they can be powerful bactericides and fungicides. Tributyltins are used as industrial biocides, eg. as antifungal agents in textiles and paper, wood pulp and paper mill systems, breweries, and industrial cooling systems. Tributyltins are also used in marine anti-fouling paint. Triphenyltins are used as active components of antifungal paints and agricultural fungicides. Other triorganotins are used as miticides and acaricides.
Diorganotins have no antifungal activity, low toxicity, and low antibacterial activity, except for diphenyltins. They are used in polymer manufacturing, as PVC heat stabilizers, catalysts, in the manufacturing of polyurethane and silicone curing.
Monoorganotins have no biocidal activity and their toxicity to mammals is very low. Methyltin, butyltin, octyltin and monoestertins are used as PVC heat stabilizers.
Tetrabutyltin starting material for the di- and tributyl compounds
Dialkyl- and monoalkyltin octylthiogylates used as heat stabilizers for polyvinyl chloride
Unlike their carbon analogues, tin compounds can also be coordinated to five atoms instead of the regular four. These hypercoordinated compounds usually have electronegative substituents for stabilization. In 2007 a room-temperature stable (in argon) all-carbon pentaorganostannane was reported  as the lithium salt with this structure:
^Synthesis and Structure of Pentaorganostannate Having Five Carbon Substituents Masaichi Saito, Sanae Imaizumi, Tomoyuki Tajima, Kazuya Ishimura, and Shigeru Nagase J. Am. Chem. Soc.2007, 129, 10974-10975 doi:10.1021/ja072478+