Tris(trimethylsilyl)phosphine
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Names | |
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Preferred IUPAC name
Tris(trimethylsilyl)phosphane | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.154.516 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C9H27PSi3 | |
Molar mass | 250.544 g·mol−1 |
Appearance | colorless liquid |
Density | 0.863 g/cm3 |
Melting point | 24 °C (75 °F; 297 K) |
Boiling point | 243–244 °C (469–471 °F; 516–517 K) |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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poison, inflammable |
GHS labelling: | |
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Danger | |
H250, H252, H315, H319, H335 | |
P210, P222, P235+P410, P261, P264, P271, P280, P302+P334, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, P407, P413, P420, P422, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tris(trimethylsilyl)phosphine is the organophosphorus compound with the formula P(SiMe3)3 (Me = methyl). It is a colorless liquid that ignites in air and hydrolyses readily.[1]
Synthesis
[edit]Tris(trimethylsilyl)phosphine is prepared by treating trimethylsilyl chloride, white phosphorus, and sodium-potassium alloy:[2]
- 1/4 P4 + 3 Me3SiCl + 3 K → P(SiMe3)3 + 3 KCl
Several other methods exist.[1]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/5/58/LEXCUMnoC_copper_phosphide_cluster_from_doi_10.1002SLASHanie.199412901.png/220px-LEXCUMnoC_copper_phosphide_cluster_from_doi_10.1002SLASHanie.199412901.png)
Reactions
[edit]The compound hydrolyzes to give phosphine:
- P(SiMe3)3 + 3 H2O → PH3 + 3 HOSiMe3
Treatment of certain acyl chlorides with tris(trimethylsilyl)phosphine gives phosphaalkynes, one example being tert-butylphosphaacetylene.[4]
Synthesis of a phosphaalkyne using tris(trimethylsilyl)phosphine.
Reaction with potassium tert-butoxide cleaves one P-Si bond, giving the phosphide salt:[5]
- P(SiMe3)3 + KO-t-Bu → KP(SiMe3)2 + Me3SiO-t-Bu
It is a reagent in the preparation of metal phosphido clusters by reaction with metal halides or carboxylates. In such reactions the silyl halide or silyl carboxylate is liberated as illustrated in this idealized reaction:
- P(SiMe3)3 + 3 CuCl → Cu3P + 3 ClSiMe3
Safety
[edit]Tris(trimethylsilyl)phosphine spontaneously ignites in air, thus it is handled using air-free techniques.
References
[edit]- ^ a b Kosarev, Sergey A.; Collier, Steven J. (2011). "Tris(trimethylsilyl)phosphine". Handbook of Reagents for Organic Synthesis. Vol. Reagents for Silicon-Mediated Organic Synthesis. pp. 422–427. doi:10.1002/047084289X.rn01332. ISBN 978-0-471-93623-7.
- ^ Becker, Gerd; Schmidt, Helmut; Uhl, Gudrun; Uhl, Werner (1990). "Tris(Trimethylsilyl)Phosphine and Lithium Bis(Trimethylsilyl)Phosphide.Bis-(Tetrahydrofuran)". Inorganic Syntheses. Vol. 27. pp. 243–9. doi:10.1002/9780470132586.ch48. ISBN 978-0-470-13258-6.
- ^ Fenske, D.; Holstein, W. (1994). "[Cu96P30{P(SiMe3)2}6(PEt3)18], a New Phosphorus-Bridged Copper Cluster". Angew. Chem. Int ed. Engl. 33 (12): 1290–1292. doi:10.1002/anie.199412901.
- ^ M. Regitz (1990). "Phosphaalkynes: new building blocks in synthetic chemistry". Chem. Rev. 90: 191–213. doi:10.1021/cr00099a007..
- ^ Russell, Christopher A.; Townsend, Nell S. (2012). "Phosphaalkynes". In Kamer, Paul C. J.; Van Leeuwen, Piet W. N. M (eds.). Phosphorus(III) Ligands in Homogeneous Catalysis. Wiley-VCH. pp. 343–354. doi:10.1002/9781118299715.ch11. ISBN 978-1-118-29971-5.