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Organophosphorus compound |
Diphenylphosphine is commonly used in laboratory as organic phosphorus compound, it is unpleasant odor colorless liquid, and it is pungent, it is easily oxidized in air and can cause spontaneous combustion, it is sensitive to air and light, it need the protection of nitrogen. It can be used as precursor to synthesize some organic phosphine ligand. By deprotonation, it can be converted to diphenylphosphine compound: Ph2PH + nBuLi → Ph2PLi + nBuH, such as 1,2-bis (diphenylphosphino) ethane and 1,3-bis (diphenylphosphino) propane phosphine ligands etc, Wittig-Horner reagents and the synthesis of quaternary phosphonium salt is usually by means of diphenylphosphino alkylation to achieve. Diphenylphosphine such as sodium and lithium diphenylphosphine and diphenylphosphine compound can add to carbon heteroatom double bond as nucleophile. For example, in the condition of concentrated hydrochloric acid at 100℃, diphenylphosphine can add to aldehyde carbon atoms of benzaldehyde: Ph2PH + PhCHO → Ph2P (O) CH2Ph, when compares with tertiary phosphine, alkalinity of diphenylphosphine is weaker. The pKa of conjugate acid diphenylphosphine is 0.03: Ph2PH2 + → Ph2PH + H + Preparation: Lithium diphenylphosphine can generated by inexpensive triphenylphosphine and the with the cancellation of water can obtain diphenylphosphine: (1) PPh3 + 2 Li → LiPPh2 + LiPh (2) LiPPh2 + H2O → Ph2PH + LiOH. |
Uses |
It can be used the intermediates of organic, catalysts. |
Chemical Properties |
Diphenylphosphine is an organophosphorus compound commonly used in laboratories. It is a clear colorless to slightly yellow liquid with unpleasant odor, irritating, easily oxidized in air and spontaneously combusts, sensitive to air and light, and needs to be protected by nitrogen. It can be used as a precursor for the synthesis of a variety of organophosphine ligands. These ligands, in turn, are used in homogeneous catalysis for many applications including: asymmetric hydrogenation, coupling chemistry, ethylene oligomerization, hydroformylation, hydration of nitriles, and polymerization of alkenes. |
Preparation |
Diphenylphosphine can be prepared from triphenylphosphine by reduction to lithium diphenylphosphide, which can be protonated to give the title compound:PPh3 + 2 Li → LiPPh2 + LiPhLiPPh2 + H2O → Ph2PH + LiOH |
InChI:InChI=1/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
Diphenyl- or bis(2-phenylethyl)phosphine...
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The reaction of indium(III) salts with P...
The invention relates to the field of ne...
Investigations on the boundaries between...
The utilization of phosphirenium ions is...
2-Amino-6-bromopyridine
triphenylphosphine
6-(diphenylphosphanyl)-2-aminopyridine
diphenylphosphane
Conditions | Yield |
---|---|
triphenylphosphine; With ammonia; sodium; at -78 ℃; for 2h;
2-Amino-6-bromopyridine; In toluene;
|
59% |
chloro-trimethyl-silane
potassium diphenylphosphine
1,1,3,3-Tetraphenyl-2-trimethylsilyl-triphosphan
(trimethylsilyl)diphenylphosphine
Tetraphenyldiphosphin
diphenylphosphane
Conditions | Yield |
---|---|
With phosphorous; Multistep reaction; 1.) toluol, -78 deg C, 2.) toluol, r.t.;
|
phenyl diphenylphosphinite
chloro-diphenylphosphine
Diphenylphosphinic chloride
diphenylisothiocyanatophosphine
dimethyldiphenylphosphonium iodide
Tetraphenyldiphosphin
(2-cyanoethyl)diphenylphosphine
diphenyl-phosphinic acid
CAS:98327-87-8
Molecular Formula:C<sub>44</sub>H<sub>32</sub>P<sub>2</sub>
Molecular Weight:622.7
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