Tributyltin hydride

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.

Tributyltin hydride

Skeletal formula of tributyltin with one explicit hydrogen added Spacefill model of tributyltin
Ball and stick model of tributyltin
Names
Systematic IUPAC name Tributylstannane[1]
Identifiers
CAS Number	688-73-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	3587329
ChEBI	CHEBI:27086 N
ChemSpider	5734 N
ECHA InfoCard	100.010.642
EC Number	211-704-4
Gmelin Reference	4258
MeSH	Tributyltin
PubChem CID	5948
UNII	4XDX163P3D Y
CompTox Dashboard (EPA)	DTXSID0040709
InChI InChI=1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;; N Key: DBGVGMSCBYYSLD-UHFFFAOYSA-N N
SMILES CCCC[SnH](CCCC)CCCC
Properties
Chemical formula	SnC 12H 28
Molar mass	291.06 g mol−1
Density	1.082 g cm−3
Boiling point	80 °C (176 °F; 353 K) at 50 Pa
Solubility in water	Slowly reacts[citation needed]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Synthesis and characterization

The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane:^[2][3]

2 "[MeSi(H)O]_n" + (Bu₃Sn)₂O → "[MeSi(OH)O]_n" + 2 Bu₃SnH

It can also be synthesized by a reduction of tributyltin chloride with lithium aluminium hydride.

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⁻¹ for ν_Sn−H.

Applications

See also: Barton–McCombie deoxygenation

It is a specialized 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^•.^[4][5] The radical abstracts a H^• from another equivalent of tributyltin hydride, propagating the chain. Tributyltin hydride's utility as a H^• donor can be attributed to its relatively weak bond strength (78 kcal/mol).^[6]

It is the reagent of choice for hydrostannylation reactions:^[7]

RC₂R′ + HSnBu₃ → RC(H)=C(SnBu₃)R′

See also

• Tributyltin
• Trimethylsilyl

References

1. "SnBu3H - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
2. Maleczka, Robert E.; Terrell, Lamont R.; Clark, Damon H.; Whitehead, Susan L.; Gallagher, William P.; Terstiege, Ina (1999). "Application of Fluoride-Catalyzed Silane Reductions of Tin Halides to the in Situ Preparation of Vinylstannanes". J. Org. Chem. 64 (16): 5958–5965. doi:10.1021/jo990491+.
3. Tormo, J.; Fu, G. C. (2002). "α-D-Ribo-hexofuranose, 3-deoxy-1,2:5,6-bis-O-(1-methylethylidene)". Org. Synth. 78: 239. doi:10.15227/orgsyn.078.0239.
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
6. Laarhoven, L. J. J.; Mulder, P.; Wayner, D.D. M. "Determination of Bond Dissociation Enthalpies in Solution by Photoacoustic Calorimetry" Acc. Chem. Res. 1999, 32, 342 doi:10.1021/ar9703443
7. Smith, Nicholas D.; Mancuso, John; Lautens, Mark (2000). "Metal-Catalyzed Hydrostannations". Chemical Reviews. 100 (8): 3257–3282. doi:10.1021/cr9902695. PMID 11749320.

Further reading

• 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