Triphenyltin hydroxide

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Triphenyltin hydroxide
Ph3SnOH.png
Triphenyltin-hydroxide-3D-spacefill.png
Names
Preferred IUPAC name
Triphenylstannanol
Identifiers
3D model (JSmol)
4139186
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.901 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-990-6
7194
KEGG
PubChem CID
RTECS number
  • WH8575000
UNII
UN number 2786 2588
  • InChI=1S/3C6H5.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H2;/q;;;;+1/p-1 Yes check.svgY
    Key: BFWMWWXRWVJXSE-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/3C6H5.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1-5H;1H2;/q;;;;+1/p-1/rC18H16OSn/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H
    Key: BFWMWWXRWVJXSE-OLMCWIPIAE
  • O[Sn](c1ccccc1)(c2ccccc2)c3ccccc3
Properties
C18H16OSn
Molar mass 367.035 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H311, H315, H318, H330, H335, H351, H361, H372, H410
P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Triphenyltin hydroxide is an organotin compound with formula Sn(C6H5)3OH. Triphenyltin hydroxide is used as a fungicide for potatoes, sugar beets, and pecans. It was first registered for use as a pesticide in the United States in 1971. [1]

Structure

Structure of solid triphenyltin hydroxide. Ph3SnOH.svg
Structure of solid triphenyltin hydroxide.

While triphenyltin hydroxide is often depicted as a monomer, it crystallizes as a polymer with a bridging hydroxide groups. [2] The Sn-O distances are 2.18 and 2.250 Å. Many organotin compounds engage in similar aggregation equilibria.

Related Research Articles

Hydroxide Chemical compound

Hydroxide is a diatomic anion with chemical formula OH. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. The corresponding electrically neutral compound HO is the hydroxyl radical. The corresponding covalently bound group –OH of atoms is the hydroxy group. Hydroxide ion and hydroxy group are nucleophiles and can act as catalysts in organic chemistry.

Tin Chemical element, symbol Sn and atomic number 50

Tin is a chemical element with the symbol Sn and atomic number 50. Tin is a silvery-colored metal that characteristically has a faint yellow hue.

Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. It was first discovered by Andreas Libavius (1550–1616) and was known as spiritus fumans libavii.

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 ((C2H5)2SnI2), discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn-C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

Tin(IV) oxide Chemical compound known as stannic oxide, cassiterite and tin ore

Tin(IV) oxide, also known as stannic oxide, is the inorganic compound with the formula SnO2. The mineral form of SnO2 is called cassiterite, and this is the main ore of tin. With many other names, this oxide of tin is an important material in tin chemistry. It is a colourless, diamagnetic, amphoteric solid.

Tributyltin oxide Chemical compound

Tributyltin oxide (TBTO) is an organotin compound chiefly used as a biocide (fungicide and molluscicide), especially a wood preservative. Its chemical formula is [(C4H9)3Sn]2O. It is a colorless viscous liquid. It is poorly soluble in water (20 ppm) but highly soluble in organic solvents. It is a potent skin irritant.

Tributyltin

Tributyltin (TBT) is an umbrella term for a class of organotin compounds which contain the (C4H9)3Sn group, with a prominent example being tributyltin oxide. For 40 years TBT was used as a biocide in anti-fouling paint, commonly known as bottom paint, applied to the hulls of ocean going vessels. Bottom paint improves ship performance and durability as it reduces the rate of biofouling (the growth of organisms on the ship's hull). The TBT slowly leaches out into the marine environment where it is highly toxic toward nontarget organisms. TBT is also an obesogen. After it led to collapse of local populations of organisms, TBT was banned.

Organogermanium compound

Organogermanium compounds are organometallic compounds containing a carbon to germanium or hydrogen to germanium chemical bond. Organogermanium chemistry is the corresponding chemical science. Germanium shares group 14 in the periodic table with silicon, tin and lead, and not surprisingly the chemistry of organogermanium is in between that of organosilicon compounds and organotin compounds.

Organolead compound

Organolead compounds are chemical compounds containing a chemical bond between carbon and lead. Organolead chemistry is the corresponding science. The first organolead compound was hexaethyldilead (Pb2(C2H5)6), first synthesized in 1858. Sharing the same group with carbon, lead is tetravalent.

Triphenyltin hydride Chemical compound

Triphenyltin hydride is the organotin compound with the formula (C6H5)3SnH. It is a white distillable oil that is soluble in organic solvents. It is often used as a source of "H·" to generate radicals or cleave carbon-oxygen bonds.

Tributyltin hydride Chemical compound

Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis.

Trimethyltin chloride Chemical compound

Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.

Tetraethyltin or tetraethyl tin is a chemical compound with the formula C
8
H
20
Sn
and molecular structure (CH3CH2)4Sn, that is, a tin atom attached to four ethyl groups. It is an important example of an organotin compound, often abbreviated as TET.

Tetramethyltin Chemical compound

Tetramethyltin is an organometallic compound with the formula (CH3)4Sn. This liquid, one of the simplest organotin compounds, is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones. It is volatile and toxic, so care should be taken when using it in the laboratory.

Dibutyltin oxide Chemical compound

Dibutyltin oxide, or dibutyloxotin, is an organotin compound with the chemical formula (C4H9)2SnO. It is a colorless solid that, when pure, is insoluble in organic solvents. It is used as a reagent and a catalyst.

Fentin acetate Chemical compound

Fentin acetate is an organotin compound with the formula (C6H5)3SnO2CCH3. It is a colourless solid that was previously used as a fungicide.

Sodium selenide Chemical compound

Sodium selenide is an inorganic compound of sodium and selenium with the chemical formula Na2Se.

Triphenyltin compounds are organotin compounds with the general formula (C6H5)3SnX. They contain the triphenyltin group, (C6H5)3Sn, or Ph3Sn, which consists of an atom of tin bonded to three phenyl groups. Examples of triphenyltins include:

Stannoxane

Stannoxane is a functional group in organotin chemistry with the connectivity SnIV-O-SnIV. Aside from the oxide group, usually 3 or 4 other substituents are attached to tin. In aqueous or aquatic environments, most organotin compounds contain this group.

Tributyltin chloride Chemical compound

Tributyltin chloride is an organotin compound with the formula (C4H9)3SnCl. It is a colorless liquid that is soluble in organic solvents.

References

  1. "R.E.D. Facts: Triphenyltin Hydroxide" (PDF). U.S. EPA.
  2. Christopher Glidewell, John N. Low, João A. S. Bomfim, Carlos A. L. Filgueiras, James L. Wardell (2002). "catena-Poly[[triphenyltin(IV)]-μ-hydroxo-κ2O:O] at 120 K". Acta Cryst. C. 58. doi:10.1107/S0108270102001798.{{cite journal}}: CS1 maint: uses authors parameter (link)