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Tributyltin hydride

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Tributyltin hydride
Skeletal formula of tributyltin with one explicit hydrogen added
Skeletal formula of tributyltin with one explicit hydrogen added
Spacefill model of tributyltin
Spacefill model of tributyltin
Ball and stick model of tributyltin
Names
Systematic IUPAC name Tributylstannane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 3587329
ChEBI
ChemSpider
ECHA InfoCard 100.010.642 Edit this at Wikidata
EC Number
  • 211-704-4
Gmelin Reference 4258
MeSH Tributyltin
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;;Key: DBGVGMSCBYYSLD-UHFFFAOYSA-N
SMILES
  • CCCC(CCCC)CCCC
Properties
Chemical formula SnC
12H
28
Molar mass 291.06 g mol
Density 1.082 g cm
Boiling point 80 °C (176 °F; 353 K)
Solubility in water Slowly reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
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.

Synthesis and characterization

The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane (Bu = CH3CH2CH2CH2):

2"(MeSiH)" + (Bu3Sn)2O → "(Me2Si2O" + 2 Bu3SnH
(Bu3Sn)2O + 2/n (MeSi(H)O)n → 2 Bu3SnH + 1/n n

The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu3Sn)2O. Its IR spectrum exhibits a strong band at 1814 cm for νSn-H.

Applications

It is a useful reagent in organic synthesis. Combined with azobisisobutyronitrile (AIBN) or by irradiation with light, tributyltin hydride converts organic halides (and related groups) to the corresponding hydrocarbon. This process occurs via a radical chain mechanism involving the radical Bu3Sn.

See also

References

  1. "SnBu3H - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. Hayashi, K.; Iyoda, J.; Shiihara, I. "Reaction of organotin oxides, alkoxides and acyloxides with organosilicon hydrides. New preparative method of organotin hydrides " J. Organomet. Chem. 1967, 10, 81. doi:10.1016/S0022-328X(00)81719-2
  3. Jordi Tormo and Gregory C. Fu (2002). "Tributylstannane (Bu3SnH)-Catalyzed Barton-McCombie deoxygenation of Alcohols: 3-Deoxy-1,2:5,6-bis-O-(1-methylethyilidine)-α-D-ribo-hexafuranose". Organic Syntheses. 78: 239.
  4. OUP catalogue page, J. Clayden, N. Greeves, S. Warren and P. Wothers, in Organic Chemistry, 2000, OUP, Oxford, ch. 39, pp. 1040-1041.
  5. T. V. (Babu) RajanBabu, Philip C. Bulman Page, Benjamin R. Buckley, "Tri-n-butylstannane" Encyclopedia of Reagents for Organic Synthesis 2004, John Wiley & Sons. doi:10.1002/047084289X.rt181.pub2
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