Triphenyltin hydride

Last updated
Triphenyltin hydride
Ph3SnH.png
Triphenyltin-hydride-3D-spacefill.png
Names
IUPAC name
Triphenylstannane
Identifiers
3D model (JSmol)
3544353
ChEBI
ChemSpider
ECHA InfoCard 100.011.789 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-967-8
6741
PubChem CID
RTECS number
  • WH8882000
UNII
  • InChI=1S/3C6H5.Sn.H/c3*1-2-4-6-5-3-1;;/h3*1-5H;; Yes check.svgY
    Key: NFHRNKANAAGQOH-UHFFFAOYSA-N Yes check.svgY
  • [H][Sn](C2=CC=CC=C2)(C3=CC=CC=C3)C1=CC=CC=C1
  • c1c(cccc1)[Sn](c2ccccc2)c3ccccc3
Properties
C18H16Sn
Molar mass 351.036 g·mol−1
Appearancecolorless
Density 1.374 g/cm3
Melting point 28 °C (82 °F; 301 K)
Boiling point 156 °C (313 °F; 429 K)(0.15 mm Hg)
insoluble
Solubility in benzene, THF soluble
Hazards
Main hazards toxic
GHS pictograms GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
GHS Signal word Danger
H301, H311, H331, H410
Flash point >230 °F
Related compounds
Related compounds
SnCl4,
(C6H5)3SnCl,
(C6H5)3SnOH
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 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.

Preparation and reactions

Ph3SnH, as it is more commonly abbreviated, is prepared by treatment of triphenyltin chloride with lithium aluminium hydride. [1] Although Ph3SnH is treated as a source of "H·", in fact it does not release free hydrogen atoms, which are extremely reactive species. Instead, Ph3SnH transfers H to substrates usually via a radical chain mechanism. This reactivity exploits the relatively good stability of "Ph3Sn·" [1]

Related Research Articles

A methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms — CH3. In formulas, the group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, it can be found on its own in any of three forms: anion, cation or radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

In chemistry, a hydride is formally the anion of hydrogen, H. The term is applied loosely. At one extreme, all compounds containing covalently bound H atoms are called hydrides: water (H2O) is a hydride of oxygen, ammonia is a hydride of nitrogen, etc. For inorganic chemists, hydrides refer to compounds and ions in which hydrogen is covalently attached to a less electronegative element. In such cases, the H centre has nucleophilic character, which contrasts with the protic character of acids. The hydride anion is very rarely observed.

In chemistry, a leaving group is a molecular fragment that departs with a pair of electrons in heterolytic bond cleavage. Leaving groups can be anions, cations or neutral molecules, but in either case it is crucial that the leaving group be able to stabilize the additional electron density that results from bond heterolysis. Common anionic leaving groups are halides such as Cl, Br, and I, and sulfonate esters such as tosylate (TsO). Fluoride (F) functions as a leaving group in the nerve agent sarin gas. Common neutral molecule leaving groups are water and ammonia. Leaving groups may also be positively charged cations (such as H+ released during the nitration of benzene); these are also known specifically as electrofuges.

Intramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule, a property or phenomenon limited to the extent of a single molecule.

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula LiAlH4. It is a grey solid. It was discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

Sodium hydride Chemical compound

Sodium hydride is the chemical compound with the empirical formula NaH. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H ions, in contrast to molecular hydrides such as borane, methane, ammonia, and water. It is an ionic material that is insoluble in organic solvents (although soluble in molten Na), consistent with the fact that H ions do not exist in solution. Because of the insolubility of NaH, all reactions involving NaH occur at the surface of the solid.

In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Sodium borohydride Chemical compound

Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a reducing agent that finds application in chemistry, both in the laboratory and on an industrial scale. It has been tested as pretreatment for pulping of wood, but is too costly to be commercialized. The compound is soluble in alcohols, certain ethers, and water, although it slowly hydrolyzes.

Benzyl group

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure C6H5CH2–. Benzyl features a benzene ring attached to a CH2 group.

Oxidative addition and reductive elimination are two important and related classes of reactions in organometallic chemistry. Oxidative addition is a process that increases both the oxidation state and coordination number of a metal centre. Oxidative addition is often a step in catalytic cycles, in conjunction with its reverse reaction, reductive elimination.

A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. In the example below the substituent R moves from carbon atom C2 to C3.

Organotin chemistry

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.

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.

Aluminium hydride Chemical compound

Aluminium hydride (also known as alane or alumane) is an inorganic compound with the formula AlH3. It presents as a white solid and may be tinted grey with decreasing particle size and impurity levels. Depending upon synthesis conditions, the surface of the alane may be passivated with a thin layer of aluminum oxide and/or hydroxide. Alane and its derivatives are used as reducing agents in organic synthesis.

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.

Helium hydride ion Chemical compound

The helium hydride ion or hydridohelium(1+) ion or helonium is a cation (positively charged ion) with chemical formula HeH+. It consists of a helium atom bonded to a hydrogen atom, with one electron removed. It can also be viewed as protonated helium. It is the lightest heteronuclear ion, and is believed to be the first compound formed in the Universe after the Big Bang.

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:

Copper hydride Chemical compound

Copper hydride is inorganic compound with the chemical formula CuHn where n ~ 0.95. It is an red solid, rarely isolated as a pure composition, that decomposes to the elements. Copper hydride is mainly produced as a reducing agent in organic synthesis and as a precursor to various catalysts.

Group 14 hydrides are chemical compounds composed of hydrogen atoms and group 14 atoms.

Nitrogen pentahydride Chemical compound

Nitrogen pentahydride, also known as ammonium hydride is a hypothetical compound with the chemical formula NH5. There are two theoretical structures of nitrogen pentahydride. One structure is trigonal bipyramidal molecular geometry type NH5 molecule. Its nitrogen atom and hydrogen atoms are covalently bounded, and its symmetry group is D3h. Another predicted structure of nitrogen pentahydride is an ionic compound, make up of an ammonium ion and a hydride ion (NH4+H-). Until now, no one has synthesized this substance, or proved its existence, and related experiments have not directly observed nitrogen pentahydride. It is only speculated that it may be a reactive intermediate based on reaction products. Theoretical calculations show this molecule is thermodynamic unstable. The reason might be similar to the instability of nitrogen pentafluoride, so the possibility of its existence is low. However, nitrogen pentahydride might exist in special conditions or high pressure. Nitrogen pentahydride was considered for use as a solid rocket fuel for research in 1966.

References

  1. 1 2 Clive, D. L. J. "Triphenylstannane" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi : 10.1002/047084289X.rt390