| |||
Names | |||
---|---|---|---|
Systematic IUPAC name
Tributylstannane
[1] | |||
Identifiers | |||
3D model (
JSmol)
|
|||
3587329 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.010.642 | ||
EC Number |
| ||
4258 | |||
MeSH | Tributyltin | ||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
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 | ||
Slowly reacts[ citation needed] | |||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane: [2] [3]
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 νSn−H.
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]
| |||
Names | |||
---|---|---|---|
Systematic IUPAC name
Tributylstannane
[1] | |||
Identifiers | |||
3D model (
JSmol)
|
|||
3587329 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.010.642 | ||
EC Number |
| ||
4258 | |||
MeSH | Tributyltin | ||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
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 | ||
Slowly reacts[ citation needed] | |||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane: [2] [3]
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 νSn−H.
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]