5849-36-5

Usage

Uses

Used in Organic Synthesis:
DIPHENYLPHOSPHINIC ANHYDRIDE is utilized as a reagent in organic synthesis, where it serves as a dehydrating agent. Its ability to remove water molecules from reactions is crucial for promoting specific chemical transformations.
Additionally, it is employed for the preparation of phosphinic acid derivatives, which are important intermediates in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used as a Flame Retardant:
In the field of material science, DIPHENYLPHOSPHINIC ANHYDRIDE is incorporated as a flame retardant. Its inclusion in materials such as textiles, plastics, and rubber helps to enhance their fire resistance, making them safer for various applications.
Used as a Polymer Additive:
Furthermore, DIPHENYLPHOSPHINIC ANHYDRIDE is used as a polymer additive in the production of different materials. Its addition can improve the thermal stability, mechanical properties, and flame retardancy of the resulting polymers, broadening their range of uses in diverse industries.

InChI:InChI=1/C24H20O3P2/c25-28(21-13-5-1-6-14-21,22-15-7-2-8-16-22)27-29(26,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H

Upstream product

• 109-99-9 tetrahydrofuran 
• 20472-52-0 iodo-diphenyl-phosphine 
• 79-37-8 oxalyl dichloride 
• 22214-04-6 sodium diphenylphosphinate 
• 80919-02-4 C₂₃H₂₂NO₅P 
• 99461-38-8 N_α-benzyloxycarbonyl-α-phenylglycine diphenylphosphinic anhydride 
• 80919-04-6 C₂₉H₂₆NO₅P 
• 4559-70-0 Diphenylphosphine oxide 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 1016-09-7 benzhydryl methyl ether 
• 1499-21-4 Diphenylphosphinic chloride 
• 5670-78-0 ethyl diphenylmethyl ether 
• 1636-15-3 (diethylamino)diphenylphosphine 
• 62-53-3 aniline 

Downstream Products

• 1135-98-4 diphenylphosphinic fluoride 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 74356-43-7 (bis(diphenylphosphonic)anhydride) tin dibromide 
• 74334-73-9 (bis(diphenylphosphonic)anhydride) tin dichloride 

Relevant academic research and scientific papers

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.

Copper-promoted oxidative-fluorination of arylphosphine under mild conditions

An efficient method for the synthesis of phosphoric fluoride via oxidative coupling between hydrophosphine oxide and NaF is reported. DDQ serves as the oxidizing reagent as well as the hydrogen acceptor. The process involves a Cu(ii) catalysis and exhibits great functional group tolerance under mild reaction conditions. the Partner Organisations 2014.

New aspects connected with the synthesis of H-phosphinate anhydrides

A novel reaction between sodium salt of phenylphosphinic acid PhP(O)(OH)H (1) and various phosphorus electrophiles, R2P(O)C1 (2; R = alkyl, aryl, alkoxy or aryloxy) has been described. The presented reaction showed a high selectivity (yield up to 96%) in the products of the symmetric phosphorus anhydrides, R2P(O)-O-(O)PR2(4), which preferentially come from the starting phosphorus electrophiles (2). The results demonstrate that the phosphorus-phosphorus mixed anhydrides, RPH(O)-O-(O)PR2(3) are unstable under basic condition and possibly decomposed with expulsion of a phosphinylidene (Ph-P=O) fragment (6).

Determination of water content in olive oil by 31P NMR spectroscopy

A method for moisture determination in olive oil using 31P NMR spectroscopy is developed. This method is based on the replacement of the hydrogen atoms of water molecules with the tagging agents 2-chloro-4,4,5,5- tetramethyl-1,3,2-dioxaphospholane and diphenylphosphinic chloride. Both reagents were successful in determining moisture in olive oil. However, only the second reagent provided a clean and instantaneous reaction under mild condition with no side reactions as observed with the first reagent. A study comparison was made to assess the agreement between the present analytical NMR method and the well-established methods of Karl Fischer titration.

Biomimetic building-up of the carbamic moiety: The intermediacy of carboxyphosphate analogues in the synthesis of N-aryl carbamate esters from arylamines and organic carbonates promoted by phosphorus acids

The reaction of aromatic amines with dimethyl carbonate (DMC) or diphenyl carbonate (DPC) in the presence of organo-phosphorus acids [Ph2P(O)OH (1); (PhO)2P(O)OH (2); (BuO)2P(O)OH/(BuO)P(O)(OH)2 equimolar mixture (3)] affords carbamate esters, ArNHC(O)OR (R = Me, Ph) with high selectivity. The catalytic role played by the P-acid has been investigated and rationalized in terms of a reaction mechanism involving the intermediate formation of a carbonic-phosphinic(phosphoric) anhydride X2P(O)OC(O)OR (X = Ph, PhO; R = Me, Ph). The proposed mechanism shows intriguing analogies with the mechanism of formation of carbamate anion in living systems by carbamoyl phosphate synthetase (CPS) enzyme. Copyright

THERMAL DISPROPORTIONATION OF DIPHENYLPHOSPHINE OXIDE AND 10H-PHENOXAPHOSPHINE 10-OXIDES

Diphenylphosphine oxide at 175 deg and 0.1 torr for one hour produced diphenylphosphinic anhydride and diphenylphosphine along with a small amount of tetraphenyldiphosphine. 10H-Phenoxaphosphine 10-oxides reacted similarly under these conditions except that the product ratios varied with ring substitution. At 100 deg and 0.1 torr 2,8-difluoro-10H-phenoxaphosphine 10-oxide reacted differently than at 175 deg, producing the diphosphine monoxide at the lower temperature. The products were identified by 31P NMR spectroscopy.

(Diphenylphosphinoyl)oxyl: An Extremely Reactive Oxygen-Centered Radical

The title radical, Ph2P(O)O., has been generated by laser flash photolysis (LFP) of the peroxide 2 (1) in CH3CN solution.It has a broad, structureless absorption extending from 400 to beyond 800 nm.Absolute bimolecular rate constants k for its reactions with various organic substrates have been measured by LFP.It has been found that Ph2P(O)O. is more reactive in hydrogen abstraction (e.g., cyclohexane, k= 2.4x1E8 M-1s-1) and addition (e.g., benzene, k= 9.1x1E8 M-1s-1) than any other organic oxygen-centered radical.Only HO. is (generally) more reactive.Although Ph2P(O)O. could not be directly detected by EPR spectroscopy , it was successfully spin-trapped with a nitrone and with alkenes and alkynes.The formation of Ph2P(O)O. in the photodecomposition but not in the thermal decomposition of 1 is supported by 31P NMR analyses of reaction products.Semiempirical AM1-PM3 calculations on H2P(O)O. are also reported.

A KINETIC STUDY OF PHOSPHINIC CARBOXYLIC MIXED ANHYDRIDES

Using 32.4 MHz (31)P n.m.r. spectroscopy, disproportionation of a series of phosphinic carboxylic mixed anhydrides derived from protected α-amino acids has been studied both as a function of the substituents at phosphorus and structure of the α-amino acid being activated.It was found that the rates of disproportionation were insignificant from a preparative aspect compared with aminolysis at 0 deg C.