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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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.

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<span class="mw-page-title-main">Tin</span> Chemical element, symbol Sn and atomic number 50

Tin is a chemical element with the symbol Sn and atomic number 50. A silvery-coloured metal, tin is soft enough to be cut with little force, and a bar of tin can be bent by hand with little effort. When bent, the so-called "tin cry" can be heard as a result of twinning in tin crystals; this trait is shared by indium, cadmium, zinc, and mercury in its solid state.

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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.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

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<span class="mw-page-title-main">Tin(IV) oxide</span> Chemical compound known as stannic oxide, cassiterite and tin ore

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<span class="mw-page-title-main">Tetrabutyltin</span> Chemical compound

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<span class="mw-page-title-main">Tributyltin</span> Group of organotin compounds

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 oceangoing 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 toxicity can lead to biomagnification or bioaccumulation within such nontarget organisms like invertebrates, vertebrates, and a variety of mammals. TBT is also an obesogen. After it led to collapse of local populations of organisms, TBT was banned.

<span class="mw-page-title-main">Organolead chemistry</span>

Organolead chemistry is the scientific study of the synthesis and properties of organolead compounds, which are organometallic compounds containing a chemical bond between carbon and lead. The first organolead compound was hexaethyldilead (Pb2(C2H5)6), first synthesized in 1858. Sharing the same group with carbon, lead is tetravalent.

<span class="mw-page-title-main">Tributyltin hydride</span> 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.

<span class="mw-page-title-main">Trimethyltin chloride</span> Chemical compound

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<span class="mw-page-title-main">Triphenyltin chloride</span> Chemical compound

Triphenyltin chloride is an organotin compound with formula Sn(C6H5)3Cl. It is a colourless solid that dissolves in organic solvents. It slowly reacts with water. The main use for this compound is as a fungicide and antifoulant. Triphenyl tin chloride is used as a chemosterilant. Triphenyl tins used as an antifeedants against potato cutworm.

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<span class="mw-page-title-main">Dibutyltin oxide</span> 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.

<span class="mw-page-title-main">Fentin acetate</span> Chemical compound

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<span class="mw-page-title-main">Tributyltin chloride</span> 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 Crystallographica Section C: Crystal Structure Communications. 58 (Pt 4): M199-201. doi:10.1107/S0108270102001798. PMID   11932514.