Tributyltin hydride: Difference between revisions

Browse history interactively ← Previous edit Next edit →Content deleted Content addedVisual WikitextInline

Revision as of 01:55, 6 January 2014 editSmokefoot (talk \| contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,246 edits →Synthesis and characterization: OS prep ref← Previous edit		Revision as of 19:28, 16 February 2014 edit undoVituzzu (talk \| contribs)Extended confirmed users4,766 editsm (Script) File renamed: File:Tributyltin.png → File:Tributyltin hydride.png File renaming criterion #3: Correct misleading names into accurate ones.Next edit →
Line 7:		Line 7:
	\| ImageSizeL1 = 121		\| ImageSizeL1 = 121
	\| ImageNameL1 = Skeletal formula of tributyltin with one explicit hydrogen added		\| ImageNameL1 = Skeletal formula of tributyltin with one explicit hydrogen added
	\| ImageFileR1 = Tributyltin.png		\| ImageFileR1 = Tributyltin hydride.png
	\| ImageFileR1_Ref = {{chemboximage\|correct\|??}}		\| ImageFileR1_Ref = {{chemboximage\|correct\|??}}
	\| ImageSizeR1 = 121		\| ImageSizeR1 = 121

Revision as of 19:28, 16 February 2014

Tributyltin hydride

Names

Systematic IUPAC name Tributylstannane

Identifiers

CAS Number

688-73-3

3D model (JSmol)

Interactive image

Beilstein Reference

3587329

ChEBI

CHEBI:27086

ChemSpider

5734

ECHA InfoCard

100.010.642

EC Number

211-704-4

Gmelin Reference

4258

MeSH

Tributyltin

PubChem CID

5948

CompTox Dashboard (EPA)

DTXSID0040709

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

SnC
₁₂H
₂₈

291.06 g mol

1.082 g cm

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 ν_Sn-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.

References

"SnBu3H - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
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
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.
OUP catalogue page, J. Clayden, N. Greeves, S. Warren and P. Wothers, in Organic Chemistry, 2000, OUP, Oxford, ch. 39, pp. 1040-1041.
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

Categories:

Misplaced Pages