cas 6303-21-5, Hypophosphorous acid | Articles data

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Synthesis of monophosphines directly from white phosphorus
Monophosphorus compounds are of enormous industrial importance due to the crucial roles they play in applications such as pharmaceuticals, photoinitiators and ligands for catalysis, among many others. White phosphorus (P4) is the key starting material for the preparation of all such chemicals. However, current production depends on indirect and inefficient, multi-step procedures. Here, we report a simple, effective ‘one-pot’ synthesis of a wide range of organic and inorganic monophosphorus species directly from P4. Reduction of P4 using tri-n-butyltin hydride and subsequent treatment with various electrophiles affords compounds that are of key importance for the chemical industry, and it requires only mild conditions and inexpensive, easily handled reagents. Crucially, we also demonstrate facile and efficient recycling and ultimately catalytic use of the tributyltin reagent, thereby avoiding the formation of substantial Sn-containing waste. Accessible, industrially relevant products include the fumigant PH3, the reducing agent hypophosphorous acid and the flame-retardant precursor tetrakis(hydroxymethyl)phosphonium chloride. [Figure not available: see fulltext.]
Scott, Daniel J.,Cammarata, Jose,Schimpf, Maximilian,Wolf, Robert
p. 458 - 464
(2021/04/09)

Oxidation of white phosphorus by peroxides in water
A mixture of hypophosphorous, phosphorous, and phosphoric acids is formed during the anaerobic oxidation of white phosphorus by peroxides [ROOН; R = Н, 3-ClC6H4CO, (СН3)3С] in water. The rate of reactions grows considerably upon adding nonpolar organic solvents. The activity series of peroxides and solvents are determined experimentally. NMR spectroscopy shows that the main product of the reaction is phosphorous acid, regardless of the nature of the peroxide and solvent. A radical mechanism of oxidation of white phosphorus by peroxides in water is proposed. It is initiated by the homolysis of peroxide with the formation of НO? radicals that are responsible for the homolytic opening of phosphoric tetrahedrons. Further oxidation and stages of the hydrolysis of intermediate phosphorus-containing compounds yield products of the reaction.
Abdreimova,Akbaeva,Polimbetova
p. 1873 - 1876
(2017/09/27)

Reactivity of phosphine oxide H3PO in the reactions with ketones
The reactivity of the electrochemically generated phosphine oxide H3PO towards ketones (acetone, ethyl methyl ketone, methyl n-propyl ketone, and tert-butyl methyl ketone) has been studied. It was found that this reaction led to the formation o
Gorbachuk,Badeeva,Babaev,Rizvanov, I. Kh.,Zinnatullin,Pavlov,Khayarov, Kh. R.,Yakhvarov
p. 1289 - 1294
(2017/02/05)

Electrochemical generation of P4 2- dianion from white phosphorus
Electrochemical reduction of elemental (white) phosphorus in an undivided cell equipped with a sacrificial metal anode (Al, Co, Nb, Sn) results in the formation of the reduced form of white phosphorus, P4 2- dianion, which was detected in solution by 31P NMR spectroscopy.
Yakhvarov,Gorbachuk,Khayarov, Kh. R.,Morozov,Rizvanov, I. Kh.,Sinyashin
p. 2423 - 2427
(2015/08/03)

Effect of a sacrificial anode material on the electrochemical generation of phosphane oxide (H3PO)
The highest yields of phosphane oxide in the title process were obtained in electrochemical cells supplied with aluminium (49%), tin (36%) or zinc (67%) anodes.
Gorbachuk, Elena V.,Khayarov, Khasan R.,Sinyashin, Oleg G.,Yakhvarov, Dmitry G.
p. 334 - 335
(2015/02/19)

Experimental evidence of phosphine oxide generation in solution and trapping by ruthenium complexes
Phosphine oxide (H3PO), the first defined compound of phosphorus in the oxidation state -1, was obtained in solution by electrochemical methods starting from white phosphorus (see picture). H3PO was characterized by NMR solution spectroscopy as a free molecule and isolated as a ligand in ruthenium(II) complexes following tautomerization to phosphinous acid, H 2P(OH).
Yakhvarov, Dmitry,Caporali, Maria,Gonsalvi, Luca,Latypov, Shamil,Mirabello, Vincenzo,Rizvanov, Ildar,Sinyashin, Oleg,Stoppioni, Piero,Peruzzini, Maurizio
p. 5370 - 5373
(2011/07/07)

Coordination and reactivity of white phosphorus and tetraphosphorus trisulphide in the presence of the fragment CpFe(dppe) [dppe = 1,2-bis(diphenylphosphino)ethane]
The reaction of [CpFe(dppe)Cl] (1) [dppe = 1,2-bis(diphenylphosphino)ethane] with one equivalent of P4 or P4S3 in the presence of a chloride scavenger, TlPF6 or AgOTf (OTf = triflate, OSO2CF3), affords the complexes [CpFe(dppe)(η1-P4)]PF6 (2) and [CpFe(dppe)(η1-Pbasal-P4S3)]OTf (3) which contain the tetrahedral P4 and the mixed P4S3 cage molecule η1-bound to the metal. Both P4 and P4S3 yield furthermore the dimetal compounds [{CpFe(dppe)}2(μ,η1:1-P4)](PF6)2 (4) and [{CpFe(dppe)}2(μ,η1:1-Papical-Pbasal-P4S3)](OTf)2 (5), which contain the tetrahedral P4 or the mixed-cage P4S3 molecule tethering two ruthenium fragments via two phosphorus atoms. All the compounds have been characterized by elemental analyses and NMR measurements. The crystal structure of 4 has been determined by X-ray diffraction methods. The complexes readily react with excess water under mild reaction conditions and the outcoming products have been identified.
Di Vaira, Massimo,Peruzzini, Maurizio,Costantini, Stefano Seniori,Stoppioni, Piero
p. 816 - 820
(2010/06/16)

Synthesis, characterization and hydrolysis of osmium tetraphosphorus complexes
The reaction of [CpOs(PPh3)2Cl] (1) with one equivalent of white phosphorus in the presence of AgOTf (OTf = triflate, OSO2CF3) as chloride scavenger affords the stable metal complex [CpOs(PPh3)2
Caporali, Maria,Di Vaira, Massimo,Peruzzini, Maurizio,Costantini, Stefano Senior,Stoppioni, Piero,Zanobini, Fabrizio
p. 152 - 158
(2010/04/01)

Electrochemical synthesis of phosphine from the lower phosphorus acids
We have studied the reduction of hypophosphorous and phosphorous acids at mercury and lead cathodes and with potassium and sodium amalgams. Both acids are found to be difficult to reduce. With the mercury cathode, the current efficiency for phosphine is w
Turygin,Smirnov,Khudenko,Nikolashin,Fedorov,Tomilov
p. 1388 - 1393
(2010/04/04)

C3′-methylene hydrogen phosphonate monomers and related compounds
The present invention is directed to nucleoside monomers wherein the 3′-O atom is replaced with a methylene group. The present invention also provides oligomers comprising a plurality of such monomers which are linked by methylenephosphonate linkages. Further, methods of preparing monomers and oligomers according to the present invention are provided.
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(2008/06/13)

Dihydorbenzofuran and related compounds useful as anti-inflammatory agents
A compound having the structure: STR1 wherein (a) W is --C(X')--NRR' or --NR--C(X')R'; (b) X and X' are independently O or S; (c) each Y is independently hydrogen or straight, branched or cyclic alkanyl having from 1 to about 3 carbon atoms, or the two Y's are bonded to form an alkanyl ring having from 3 to about 7 carbon atoms; (d) Z is unsubstituted branched or cyclic alkyl, or unsubstituted or alkanyl-substituted phenyl or benzyl, Z having from 3 to about 10 atoms other than hydrogen; (e) R and R' are each independently selected from hydrogen, hydroxy straight, branched or substituted alkyl having from 1 to about 6 carbon atoms, and cyclic alkyl having from 3 to about 7 carbon atoms; unsubstituted or substituted aryl, heteroaryl or heterocyclic groups; or R and R' are bonded together to form a ring having from from 3 to about 8 atoms wherein about 1 to about 4 atoms may be heteroatoms; pharmaceutical compositions comprising such compounds, and methods of treating inflammation or pain using such compounds.
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(2008/06/13)

LOW-TEMPERATURE OXIDATION OF RED PHOSPHORUS
The oxidation kinetics of red phosphorus in the low-temperature region have been investigated, and conditions favorable for the accumulation of various oxidation products (H3PO2, H3PO3, and H3PO4) have been determined.
Shechkov, G. T.,Domin, A. V.,Neskorodova, N. M.
p. 1501 - 1504
(2007/10/02)

REACTION OF SALTS OF HYPOPHOSPHOROUS ACID WITH ALKYLHALIDES
Alkali salts of hypophosphorous acid undergo an exchange reaction with alkyl halides.From the interaction between potassium hypophosphite and allyl bromide or 3-chloro-1,2-propanediol phosphonous acids are formed.A mechanism of the interaction, a variant of the Michaelis-Becker reaction, is proposed.
Devedjiev, I.,Ganev, V.,Stefanova, R.,Borissov, G.
p. 261 - 266
(2007/10/02)

The Influence of Preliminary Ultraviolet Irradiation on the Thermal Decomposition of Copper Hypophosphite
The influence of preliminary ultraviolet irradiation on the thermal decomposition of crystalline copper hypophosphite has been observed.It is shown that the effect is caused by the formation of an acid on photolysis, which accelerates the thermal decomposition.
Mikhailov, Yu. I.,Lomovskii, O. I.,Lushnikov, A. Ya.
p. 1470 - 1472
(2007/10/02)