Organophosphorus compound

organophosphorusorganophosphorus chemistryorganophosphineorganophosphorus compoundsalkylphosphinecarbon–phosphorus bondOrganic phosphorusorgano-phosphorus chemistryorganophosphateorganophosphorus anion
Organophosphorus compounds are organic compounds containing phosphorus.wikipedia
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Sarin

sarin gasGBnerve gas
Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.
Sarin (NATO designation GB [short for G-series, "B"]), is an extremely toxic synthetic organophosphorus compound.

VX (nerve agent)

VXVX nerve agentVX gas
Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.
VX is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate.

Phosphorus

PP 4 phosphoric
Organophosphorus compounds are organic compounds containing phosphorus.
Other applications include organophosphorus compounds in detergents, pesticides, and nerve agents.

Phosphonate

phosphonic acidsphosphonic acidphosphonates
Phosphonates are esters of phosphonic acid and have the general formula RP(=O)(OR') 2.
Phosphonates and phosphonic acids are organophosphorus compounds containing C−PO(OH) 2 or C−PO(OR) 2 groups (where R = alkyl, aryl).

Glyphosate

Roundupglycosphateglyphosates
Phosphonates have many technical applications, a well-known member being glyphosate, better known as Roundup.
It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase.

Trimethyl phosphite

trimethylphosphiteP(OCH 3 ) 3
For example, dimethylmethylphosphonate (see figure above) arises from the rearrangement of trimethylphosphite, which is catalyzed by methyl iodide.
Trimethyl phosphite is an organophosphorus compound with the formula P(OCH 3 ) 3, often abbreviated P(OMe) 3.

Kabachnik–Fields reaction

The Kabachnik–Fields reaction is a method for the preparation of aminophosphonates.
In organophosphorus chemistry, the Kabachnik–Fields reaction is a three-component organic reaction forming α-aminomethylphosphonates from an amine, a carbonyl compound, and a dialkyl phosphonate, (RO) 2 P(O)H (that are also called dialkylphosphites).

Triphenylphosphine oxide

Ph 3 P=OPh 3 POtributylphosphine oxide
The P=O bond is very polar with a dipole moment of 4.51 D for triphenylphosphine oxide.
Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C 6 H 5 ) 3, also written as Ph 3 PO or PPh 3 O (Ph = C 6 H 5 ).

Tetrakis(hydroxymethyl)phosphonium chloride

tetrakis(hydroxymethyl)phosphonium
From the commercial perspective, the most important member is tetrakis(hydroxymethyl)phosphonium chloride, [P(CH 2 OH) 4 ]Cl, which is used as a fire retardant in textiles.
Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH 2 OH) 4 ]Cl.

Organic compound

syntheticorganicorganic compounds
Organophosphorus compounds are organic compounds containing phosphorus.
Organic compounds can also be classified or subdivided by the presence of heteroatoms, e.g., organometallic compounds, which feature bonds between carbon and a metal, and organophosphorus compounds, which feature bonds between carbon and a phosphorus.

Phosphinite

Intermediate between phosphites and phosphines are phosphonites (P(OR) 2 R') and phosphinite (P(OR)R' 2 ).
Phosphinites are organophosphorus compounds with the formula P(OR)R 2.

Phosphine

phosphinesPH 3 phosphane
The parent compound of the phosphines is PH 3, called phosphine in the US and British Commonwealth, but phosphane elsewhere.
Phosphines are also a group of organophosphorus compounds with the formula R 3 P (R = organic derivative).

Phosphorane

methylenetriphenylphosphorane
The parent phosphorane (σ 5 λ 5 ) is PH 5, which is unknown.
A phosphorane (IUPAC name: λ 5 -phosphane) is a functional group in organophosphorus chemistry with pentavalent phosphorus.

Phosphonite

methylphosphonous acid
Intermediate between phosphites and phosphines are phosphonites (P(OR) 2 R') and phosphinite (P(OR)R' 2 ).
Phosphonites are organophosphorus compounds with the formula P(OR) 2 R. They are found in some pesticides and are used as ligands.

Trimethylphosphine

PMe 3 P(CH 3 ) 3 (CH 3 ) 3 P
Phosphines are often less basic than corresponding amines, for instance the phosphonium ion itself has a pK a of −14 compared to 9.21 for the ammonium ion; trimethylphosphonium has a pK a of 8.65 compared to 9.76 for trimethylammonium.
Trimethylphosphine is the organophosphorus compound with the formula P(CH 3 ) 3, commonly abbreviated as PMe 3.

Triphenylphosphine

PPh 3 triphenyl phosphineP(C 6 H 5 ) 3
From the commercial perspective, the most important phosphine is triphenylphosphine, several million kilograms being produced annually.
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5 ) 3 - often abbreviated to PPh 3 or Ph 3 P. It is widely used in the synthesis of organic and organometallic compounds.

Phosphorus trichloride

PCl 3 PCl3phosphorus chloride
It is prepared from the reaction of chlorobenzene, PCl 3, and sodium.
Phosphorus trichloride is the precursor to organophosphorus compounds that contain one or more P(III) atoms, most notably phosphites and phosphonates.

Phosphole

chlorophospholenium
Whereas the lone pair on nitrogen is delocalized in pyrrole, the lone pair on phosphorus atom in the phosphorus equivalent of pyrrole (phosphole) is not.
These compounds are of theoretical interest but also serve as ligands for transition metals and as precursors to more complex organophosphorus compounds.

Phosphine ligand

phosphineligandsphosphine ligand family
Two major applications are as reagents in the Wittig reaction and as supporting phosphine ligands in homogeneous catalysis.
Phosphine ligands are phosphines, compound of the formula PRR'R" (R, R', R" = H, alkyl, aryl, etc) that are used as ligands in metal complexes, often related to organometallic chemistry and homogeneous catalysis.

Phosphate

phosphatesphosphate groupinorganic phosphate
:In the environment, these compounds break down via hydrolysis to eventually afford phosphate and the organic alcohol or amine from which they are derived.

Phosphaalkene

phosphaalkenes
Compounds with carbon phosphorus(III) multiple bonds are called phosphaalkenes (R 2 C=PR) and phosphaalkynes (RC≡P).
Phosphaalkenes (IUPAC name: alkylidenephosphanes) are organophosphorus compounds with double bonds between carbon and phosphorus(III) with the formula R 2 C=PR.

Rauhut–Currier reaction

Rauhut-Currier reaction
Phosphines are nucleophilic catalysts in organic synthesis, e.g. the Rauhut–Currier reaction and Baylis-Hillman reaction.
The Rauhut–Currier reaction, also called the vinylogous Morita–Baylis–Hillman reaction, is an organic reaction describing (in its original scope) the dimerization or isomerization of electron-deficient alkenes such as enones by action of an organophosphine of the type R 3 P. In a more general description the RC reaction is any coupling of one active alkene / latent enolate to a second Michael acceptor, creating a new C–C bond between the alpha-position of one activated alkene and the beta-position of a second alkene under the influence of a nucleophilic catalyst.

Organophosphate

organophosphatesphosphate esterorganophosphorous
Phosphate esters have the general structure P(=O)(OR) 3 feature P(V).
Organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure O=P(OR) 3.

Phosphaalkyne

phosphinocarbene
Compounds with carbon phosphorus(III) multiple bonds are called phosphaalkenes (R 2 C=PR) and phosphaalkynes (RC≡P).
In chemistry, phosphaalkynes (IUPAC name: alkylidynephosphanes) are organophosphorus compounds that have a phosphorus-carbon triple bond, giving them a general formula of (R-C≡P).

Chlorodiphenylphosphine

Ph 2 PClPPh 2 Cl
Chlorodiphenylphosphine is an organophosphorus compound with the formula (C 6 H 5 ) 2 PCl, abbreviated Ph 2 PCl.