Names | |
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Preferred IUPAC name Tris(trimethylsilyl)phosphane | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.154.516 |
EC Number |
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PubChem CID | |
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 | poison, inflammable |
GHS labelling: | |
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). |
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]
Tris(trimethylsilyl)phosphine is prepared by treating trimethylsilyl chloride, white phosphorus, and sodium-potassium alloy: [2]
Several other methods exist. [1]
The compound hydrolyzes to give phosphine:
Treatment of certain acyl chlorides with tris(trimethylsilyl)phosphine gives phosphaalkynes, one example being tert-butylphosphaacetylene. [4]
Reaction with potassium tert-butoxide cleaves one P-Si bond, giving the phosphide salt: [5]
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:
Tris(trimethylsilyl)phosphine spontaneously ignites in air, thus it is handled using air-free techniques.
Tetrahedrane is a hypothetical platonic hydrocarbon with chemical formula C4H4 and a tetrahedral structure. The molecule would be subject to considerable angle strain and has not been synthesized as of 2023. However, a number of derivatives have been prepared. In a more general sense, the term tetrahedranes is used to describe a class of molecules and ions with related structure, e.g. white phosphorus.
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.
In chemistry, a phosphide is a compound containing the P3− ion or its equivalent. Many different phosphides are known, with widely differing structures. Most commonly encountered on the binary phosphides, i.e. those materials consisting only of phosphorus and a less electronegative element. Numerous are polyphosphides, which are solids consisting of anionic chains or clusters of phosphorus. Phosphides are known with the majority of less electronegative elements with the exception of Hg, Pb, Sb, Bi, Te, and Po. Finally, some phosphides are molecular.
In chemistry, a phosphaalkyne is an organophosphorus compound containing a triple bond between phosphorus and carbon with the general formula R-C≡P. Phosphaalkynes are the heavier congeners of nitriles, though, due to the similar electronegativities of phosphorus and carbon, possess reactivity patterns reminiscent of alkynes. Due to their high reactivity, phosphaalkynes are not found naturally on earth, but the simplest phosphaalkyne, phosphaethyne (H-C≡P) has been observed in the interstellar medium.
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
Sodium phosphide is the inorganic compound with the formula Na3P. It is a black solid. It is often described as Na+ salt of the P3− anion. Na3P is a source of the highly reactive phosphide anion. It should not be confused with sodium phosphate, Na3PO4.
Hexamethyldisilane (TMS2) is the organosilicon compound with the formula Si2(CH3)6, abbreviated Si2Me6. It is a colourless liquid, soluble in organic solvents.
Silylation is the introduction of one or more (usually) substituted silyl groups (R3Si) to a molecule. Silylations are core methods for production of organosilicon chemistry. Silanization involves similar methods but usually refers to attachment of silyl groups to solids.
The Abramov reaction is the related conversions of trialkyl to α-hydroxy phosphonates by the addition to carbonyl compounds. In terms of mechanism, the reaction involves attack of the nucleophilic phosphorus atom on the carbonyl carbon. It was named after the Russian chemist Vasilii Semenovich Abramov (1904–1968) in 1957.
tert-Butylphosphaacetylene is an organophosphorus compound. Abbreviated t-BuCP, it was the first example of an isolable phosphaalkyne. Prior to its synthesis, the double bond rule had suggested that elements of Period 3 and higher were unable to form double or triple bonds with lighter main group elements because of weak orbital overlap. The synthesis of t-BuCP discredited much of the double bond rule and opened new studies into the formation of unsaturated phosphorus compounds.
Metal bis(trimethylsilyl)amides are coordination complexes composed of a cationic metal M with anionic bis(trimethylsilyl)amide ligands (the −N 2 monovalent anion, or −N 2 monovalent group, and are part of a broader category of metal amides.
Tris(trimethylsilyl)amine is the simplest tris(trialkylsilyl)amine which are having the general formula (R3Si)3N, in which all three hydrogen atoms of the ammonia are replaced by trimethylsilyl groups (-Si(CH3)3). Tris(trimethylsilyl)amine has been for years in the center of scientific interest as a stable intermediate in chemical nitrogen fixation (i. e. the conversion of atmospheric nitrogen N2 into organic substrates under normal conditions).
Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.
Tris(trimethylsilyl)silane is the organosilicon compound with the formula (Me3Si)3SiH (where Me = CH3). It is a colorless liquid that is classified as a hydrosilane since it contains an Si-H bond. The compound is notable as having a weak Si-H bond, with a bond dissociation energy estimated at 84 kcal/mol. For comparison, the Si-H bond in trimethylsilane is 94 kcal/mol. With such a weak bond, the compound is used as a reagent to deliver hydrogen atoms. The compound has been described as an environmentally benign analogue of tributyltin hydride.
Tetrakis(trimethylsilyl)silane is the organosilicon compound with the formula (Me3Si)4Si (where Me = CH3). It is a colorless sublimable solid with a high melting point. The molecule has tetrahedral symmetry. The compound is notable as having silicon bonded to four other silicon atoms, like in elemental silicon.
Tris(trimethylsilyl)methane is the organosilicon compound with the formula (tms)3CH (where tms = (CH3)3Si). It is a colorless liquid that is highly soluble in hydrocarbon solvents. Reaction of tris(trimethylsilyl)methane with methyl lithium gives tris(trimethylsilyl)methyllithium, called trisyllithium. Trisyllithium is useful in Petersen olefination reactions:
Niobium(III) chloride also known as niobium trichloride is a compound of niobium and chlorine. The binary phase NbCl3 is not well characterized but many adducts are known.
In chemistry, transition metal silyl complexes describe coordination complexes in which a transition metal is bonded to an anionic silyl ligand, forming a metal-silicon sigma bond. This class of complexes are numerous and some are technologically significant as intermediates in hydrosilylation. These complexes are a subset of organosilicon compounds.
In chemistry, salt-free reduction describes methodology for reduction of metal halides by electron-rich trimethylsilyl reagents. Traditional reductions of metal halides are accomplished with alkali metals, a process that cogenerates alkali metal salts. Using the salt-free reduction, the reduction of metal halides is accompanied by formation of neutral organic compounds that can be easily removed from the inorganic or organometallic product. In addition to the reduction of metal halides, the reagents associated with this methodology are applicable to deoxygenation of organic substrates.
1-Phosphaallenes is are allenes in which the first carbon atom is replaced by phosphorus, resulting in the structure: -P=C=C<.