23176-18-3

Usage

Uses

Used in Organometallic Chemistry:
BIS(DIPHENYLPHOSPHINO)METHANE MONOOXIDE is used as a ligand for organometallic complexes, providing stability and enhancing the reactivity of metal centers. Its ability to bind metal ions effectively makes it a valuable component in the development of organometallic compounds.
Used in Catalysis:
In the field of catalysis, BIS(DIPHENYLPHOSPHINO)METHANE MONOOXIDE is used as a stabilizing agent for metal complexes. It helps to improve the efficiency and selectivity of catalytic processes by modulating the electronic and steric properties of the active sites.
Used in Pharmaceutical Synthesis:
BIS(DIPHENYLPHOSPHINO)METHANE MONOOXIDE is used as a ligand in the synthesis of pharmaceuticals. Its coordination with metal ions can lead to the development of new drugs with improved properties, such as increased potency or selectivity.
Used in Agrochemical Synthesis:
In the agrochemical industry, BIS(DIPHENYLPHOSPHINO)METHANE MONOOXIDE is employed as a ligand for the synthesis of agrochemicals. Its role in stabilizing metal complexes can contribute to the development of more effective and environmentally friendly pesticides and fertilizers.
Used in Specialty Chemicals Synthesis:
BIS(DIPHENYLPHOSPHINO)METHANE MONOOXIDE is also used in the synthesis of specialty chemicals, where its unique binding properties can lead to the creation of new materials with specific applications in various industries.

InChI:InChI=1/C25H22OP2/c26-28(24-17-9-3-10-18-24,25-19-11-4-12-20-25)21-27(22-13-5-1-6-14-22)23-15-7-2-8-16-23/h1-20H,21H2

Upstream product

• 67-56-1 methanol 
• 116467-64-2 N-Trimethylsilyl 
• 1079-66-9 chloro-diphenylphosphine 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 64-18-6 formic acid 
• 829-85-6 diphenylphosphane 
• 2071-20-7 bis-diphenylphosphinomethane 
• 2071-21-8 bis(diphenylphosphoryl)methane 
• 696-28-6 dichlorophenylarsine 
• 4451-96-1 diphenyl(trimethylsilylmethyl)phosphane 

Downstream Products

• 73395-68-3 methylenebis(diphenylphosphine) monoxide monosulfide 
• 1707-03-5 diphenyl-phosphinic acid 
• 10038-33-2 2-[(1E)-2-(diphenylphosphino)ethenyl]pyridine 
• 2071-21-8 bis(diphenylphosphoryl)methane 
• 94394-66-8 [(E)-2-(4-Nitro-phenyl)-vinyl]-diphenyl-phosphane 
• 215815-00-2 [bis(diphenylphosphino)methane-monoxide-κ(2)-P,O](chloro)(methyl)palladium(II) * CH2Cl2 
• 240803-86-5 [(η(6)-cymene)RuCl2(η(1)-Ph2PCH2P(O)Ph2)] 
• 289689-08-3 [[bis(diphenylphosphino)methane-monoxide-κ-2-P,O](acetonitrile)(methyl) palladium(II)] hexafluoroantimonate 
• 215814-86-1 (η(3)-allyl)[bis(diphenylphosphino)methane-monoxide-κ(1)-P](iodo)palladium(II) 
• 289689-03-8 [[bis(diphenylphosphino)methane-monoxide-κ-2-P,O](acetonitrile)(methyl) palladium(II)] tetrafluoroborate 
• 189272-60-4 ((C₆H₅)2PCH₂P(O)(C₆H₅)2)Pd(C₆H₄N₂C₆H₅)⁽¹⁺⁾*SbF₆^(1-)=[((C₆H₅)2PCH₂P(O)(C₆H₅)2)Pd(C₆H₄N₂C₆H₅)]SbF₆ 

Relevant academic research and scientific papers

Diastereoselective Rhodium Catalyzed [4 + 2] Cycloisomerization of Allenes

A diastereoselective [4 + 2] cycloisomerization of asymmetric allenyl dienes is reported. The asymmetric dienyl allenes are synthesized using the method reported by Ma. These substrates readily undergo diastereoselective intramolecular rhodium catalyzed [4 + 2] cycloisomerization analogous to thermal intramolecular Diels-Alder reactions. Overall, 29 examples are presented with tethers possessing nitrogen, oxygen, and carbon. Diastereoselectivities range from 99:1 to 90:10 in most examples.

31P NMR spectroscopic analysis on photooxidation of 1,n-bis(diphenylphosphino)alkanes with the aid of DFT calculations

The chloroform-d solution of diphosphine, 1,n-bis(diphenylphosphino)alkane (Ph2P(CH2)nPPh2; n = 1-6), was photolyzed with light from a xenon lamp in air. The progress of the reaction was followed by 31P NMR spectroscopy. The observed spectral change showed that the diphosphine is initially oxidized to diphosphine monoxide, Ph2P(═O)(CH2)nPPh2, which is further oxidized to diphosphine dioxide, Ph2P(═O)(CH2)nP(═O)Ph2. The oxidation of the diphosphine to the diphosphine monoxide took place according to first-order kinetics with respect to the concentration of the diphosphine, the first-order rate constant, kobs, being larger with increasing number of the methylene units in the spacer. The observation in kinetics is interpreted based on the conformation of the diphosphine radical cation intermediate initially generated by electron transfer from the photoexcited diphosphine to oxygen. Density functional theory (DFT) calculations predict that the diphosphine radical cation takes “folded” conformation where two phosphorus atoms are arranged closely to each other. The “folded” conformer of the diphosphine radical cation results from electrostatic interaction of these two phosphorus atoms. This conformer explains the observed dependency of kobs on the length of the spacer in the diphosphine.

Rearrangement and redistribution reaction of Ph2PCH2TMS with PhAsCl2 or AsCl3

The attempted synthesis of bis(diphenylphosphinomethyl) phenylarsane and tris(diphenylphosphinomethyl) arsane through condensation of chloro arsanes and diphenyl (trimethylsilylmethyl) phosphane yielded a number of side products originating from migratory and redox-reactions in addition to the targeted ligands. An unexpected, 1,3,4-phosphadiarssolan-1-ium salt was obtained and crystallographically characterized as an A-shaped chlorido adduct.

Zero-Valent Amino-Olefin Cobalt Complexes as Catalysts for Oxygen Atom Transfer Reactions from Nitrous Oxide

The synthesis and characterization of several zero-valent cobalt complexes with a bis(olefin)-amino ligand is presented. Some of these complexes proved to be efficient catalysts for the selective oxidation of secondary and allylic phosphanes, as well as diphosphanes, even with a direct P?P bond. With 5 mol % catalyst loadings the oxidations proceed under mild conditions (25–70 °C, 7–22 h, 2 bar N2O) and afford good to excellent yields (65–98 %). In this process, the greenhouse gas N2O is catalytically converted into benign N2and added-value organophosphorus compounds, some of which are difficult to obtain otherwise.

Intramolecular stabilization of the phosphine radical cation by the second phosphorus atom during the photooxidation of diphosphines:31P NMR spectroscopic analysis

Diphosphines, Ph2P(CH2)nPPh2 1 (n = 1, 2, 3, 4, and 6), were photolyzed by a xenon lamp in air. The 31P NMR spectroscopic analysis of the reaction showed that 1 is oxidized, according to first-order kinetics, to the monoxide, which is further oxidized to the dioxide. The dependence of the rate constants for the first oxidation on the chain-length n in 1 is interpreted in terms of the orientation of the p-orbitals on the two phosphorus atoms in the intermediate, the diphosphine radical cation.

Synthesis of phosphorus(V)-stabilized geminal dianions. the cases of mixed P=X/PBH3 (X = S, O) and P=S/SiMe3 derivatives

The monodeprotonation of [CH2(PPh2BH 3)(PPh2=E)] (E = S (6), O (7)) afforded [CH(PPh 2BH3)(PPh2=E)]- (E = S (6 -), O (7-)), whose structures were confirmed by X-ray crystallography. The kinetics of the second deprotonation appeared to be crucial in efficient synthesis of the corresponding dianions. Thus, the double deprotonation of 6 only led to 62-; the analogous reaction with 7 was slower and resulted only in the partial formation of 72-. Double deprotonation of the compound [CH2(SiMe3)(PPh 2=S)] (8) also resulted in the partial formation of [C(SiMe 3)(PPh2=S)]2- (82-), whose structure was confirmed by X-ray crystallography. The rare monomeric Mg carbene compound [MgC(PPh2BH3)(PPh2=S)] (9) was obtained by the reaction of 6 with Mg(nBu)2. The X-ray structure of 9 is presented.

Selective mono reduction of bis-phosphine oxides under mild conditions

Bis-phosphine oxides can be selectively reduced to bis-phosphine monoxides under exceptionally mild conditions using triflic anhydride and a thiol. The Royal Society of Chemistry.

A novel mild deprotection method for phosphine-boranes

Treatment of phosphine-boranes with molecular sieves 4A in a mixture of an ethereal solvent and an alcohol provided deprotected free phosphines in quantitative yields. The phosphines can be obtained by a simple filtration/crystallization procedure in most cases. It should be noted that the current method is successfully applied to the deprotection of a phosphite-borane for the first time.

A practical synthesis of the first P-phosphinoylmethyl-λ5-phosphazenes

The new N-aryl-P,P-diphenyl-P-(diphenylphosphinoyl)methyl-λ5-phosphazenes 2 have been prepared by three different approaches starting from the commercially available bis(diphenylphosphino)methane. Either oxidation of the mono-λ5-phosphazenes 3 or imination of the monoxide 4 yielded compounds 2 in moderate yields. The third method involved deprotonation of the easily accesible aminophosphonium salts 5.

Facile and general synthesis of polyphosphane polyoxides with (O)PCP(O) linkages

Polyphosphane polyoxides with (O)PCP(O) linkages are powerful chelating agents for extraction of actinides from nuclear wastes. They are obtained either by the Michaelis-Arbuzov reaction of chloromethylphosphane oxides and phosphorus(III) esters, or by the reaction of phosphane oxide carbanions with chlorophosphanes. With the latter method, the addition of a phosphane oxide carbanion in excess allowed us to overcome a transmetallation reaction and thereby obtain polyphosphane polyoxides in good yields. The 1H-NMR spectra of the PCH2P groups show the influence of the different R groups attached to the phosphorus atoms. We determined the coupling constants and the chemical shifts of these spin systems.