:Tris(trimethylsilyl)phosphine
{{Chembox
| ImageFile = P(tms)3.png
| ImageSize =
| ImageAlt =
| PIN = Tris(trimethylsilyl)phosphane
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 15573-38-3
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChemSpiderID = 239909
| EINECS = 626-081-8
| PubChem = 272683
| StdInChI=1S/C9H27PSi3/c1-11(2,3)10(12(4,5)6)13(7,8)9/h1-9H3
| StdInChIKey = OUMZKMRZMVDEOF-UHFFFAOYSA-N
| SMILES = C[Si](C)(C)P([Si](C)(C)C)[Si](C)(C)C
}}
|Section2={{Chembox Properties
| C=9|H=27|Si=3|P=1
| MolarMass =
| Appearance = colorless liquid
| Density = 0.863 g/cm3
| MeltingPtC = 24
| BoilingPtC = 243-244
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards = poison, inflammable
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|250|252|315|319|335}}
| PPhrases = {{P-phrases|210|222|235+410|261|264|271|280|302+334|302+352|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|405|407|413|420|422|501}}
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite encyclopedia|title=Tris(trimethylsilyl)phosphine|author1= Kosarev, Sergey A.|author2=Collier, Steven J.|encyclopedia=Handbook of Reagents for Organic Synthesis|volume=Reagents for Silicon-Mediated Organic Synthesis|year=2011|pages=422–427|doi=10.1002/047084289X.rn01332 |isbn=978-0-471-93623-7}}
Synthesis
Tris(trimethylsilyl)phosphine is prepared by treating trimethylsilyl chloride, white phosphorus, and sodium-potassium alloy:{{cite book|title=Inorganic Syntheses|author1=Becker, Gerd|author2=Schmidt, Helmut|author3=Uhl, Gudrun|author4=Uhl, Werner|chapter=Tris(Trimethylsilyl)Phosphine and Lithium Bis(Trimethylsilyl)Phosphide.Bis-(Tetrahydrofuran) |year=1990|volume=27|pages=243–9|doi=10.1002/9780470132586.ch48|isbn=978-0-470-13258-6|url=http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-58230 }}
:1/4 P4 + 3 Me3SiCl + 3 K → P(SiMe3)3 + 3 KCl
File:LEXCUMnoC copper phosphide cluster from doi 10.1002SLASHanie.199412901.png
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.{{cite journal|author=M. Regitz|title=Phosphaalkynes: new building blocks in synthetic chemistry|journal=Chem. Rev.|year=1990|volume=90|pages=191–213|doi=10.1021/cr00099a007}}.
:Image:Cyaphid.svg using tris(trimethylsilyl)phosphine.]]
Reaction with potassium tert-butoxide cleaves one P-Si bond, giving the phosphide salt:{{cite book|chapter=Phosphaalkynes
|author1=Russell, Christopher A. |author2=Townsend, Nell S.|editor1=Kamer, Paul C. J. |editor2=Van Leeuwen, Piet W. N. M
|title=Phosphorus(III) Ligands in Homogeneous Catalysis|year=2012|pages=343–354|publisher=Wiley-VCH|doi=10.1002/9781118299715.ch11|isbn=978-1-118-29971-5}}
: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.