Tris(trimethylsilyl)phosphine

Names
Preferred IUPAC name

Tris(trimethylsilyl)phosphane

Identifiers

CAS Number

* 15573-38-3 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 239909

EC Number |

* 626-081-8

PubChem CID

* 272683

InChI

* InChI=1S/C9H27PSi3/c1-11(2,3)10(12(4,5)6)13(7,8)9/h1-9H3

Key: OUMZKMRZMVDEOF-UHFFFAOYSA-N

SMILES

* C[Si](C)(C)P([Si](C)(C)C)[Si](C)(C)C

Properties

Chemical formula

| 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
Main hazards | poison, inflammable
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H250, H252, H315, H319, H335

GHS precautionary statements

| P210, P222, P235+410, P261, P264, P271, P280, P302+334, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, 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).

Infobox references

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]

## Contents

* 1 Synthesis
* 2 Reactions
* 3 Safety
* 4 References

## Synthesis

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]

Copper phosphide cluster Cu96P30{P(SiMe3)2}6(PEt3)18 with C and H atoms omitted for clarity (red=Cu, purple=P, tan=Si). Tris(trimethylsilyl)phosphine the reagent used to install the phosphide ligands.[3]

## Reactions

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

Tris(trimethylsilyl)phosphine spontaneously ignites in air, thus it is handled using air-free techniques.

## References

1. ↑ 1.0 1.1 Kosarev, Sergey A.; Collier, Steven J. (2011). "Tris(trimethylsilyl)phosphine". Handbook of Reagents for Organic Synthesis. Reagents for Silicon-Mediated Organic Synthesis. pp. 422–427. doi:10.1002/047084289X.rn01332. ISBN 978-0471936237.
2. ↑ Becker, Gerd; Schmidt, Helmut; Uhl, Gudrun; Uhl, Werner (1990). Tris(trimethylsilyl)phosphine and lithium bis(trimethylsilyl)phosphide·bis(tetrahydrofuran). Inorganic Syntheses. 27. pp. 243–9. doi:10.1002/9780470132586.ch48. ISBN 9780470132586.
3. ↑ 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.
4. ↑ M. Regitz (1990). "Phosphaalkynes: new building blocks in synthetic chemistry". Chem. Rev. 90: 191–213. doi:10.1021/cr00099a007. .
5. ↑ Russell, Christopher A.; Townsend, Nell S. (2012). "Phosphaalkynes". Phosphorus(III) Ligands in Homogeneous Catalysis. Wiley-VCH. pp. 343–354. doi:10.1002/9781118299715.ch11. ISBN 9781118299715.

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*[CID]: Compound ID
*[H250]: Catches fire spontaneously if exposed to air
*[H252]: Self-heating in large quantities: may catch fire
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P222]: Do not allow contact with air
*[P235+410]: Keep cool. Protect from sunlight
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+334]: IF ON SKIN: Immerse in cool water/wrap in wet bandages
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P407]: Maintain air gap between stacks/pallets
*[P413]: Store bulk masses greater than … kg/… lbs at temperatures not exceeding … °C/… °F
*[P420]: Store away from other materials
*[P422]: Store contents under …
*[P501]: Dispose of contents/container to …