1707-03-5

Basic information

• Product Name: Diphenylphosphinic acid
• Synonyms: AURORA KA-1519;DIPHENYLPHOSPINIC ACID;DIPHENYLPHOSPHINIC ACID;DIPHENYLPHOSPHONIC ACID;diphenyl-phosphinicaci;Hydroxydiphenylphosphine oxide;Phosphinic acid, diphenyl-;Diphenylphosphine acid
• CAS NO: 1707-03-5
• Molecular Formula: C₁₂H₁₁O₂P
• Molecular Weight: 218.19
• EINECS: 216-948-5
• Product Categories: Organic Building Blocks;Phosphonic/Phosphinic Acids;Phosphorus Compounds;Morpholines/Thiomorpholines
• Mol File: 1707-03-5.mol
• Article Data: 119

Chemical Properties

• Melting Point: 193-195 °C(lit.)
• Boiling Point: 446.2 °C at 760 mmHg
• Flash Point: 223.7 °C
• Appearance: White/Fine Crystalline Solid
• Density: 1.25 g/cm³
• Vapor Pressure: 9.59E-09mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: Store below +30°C.
• Solubility: 0.1 M NaOH: soluble0.5g/10 mL, clear, colorless
• PKA: 2.30±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 2804567
• CAS DataBase Reference: Diphenylphosphinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenylphosphinic acid(1707-03-5)
• EPA Substance Registry System: Diphenylphosphinic acid(1707-03-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: SZ5315000
• Hazardous Substances Data: 1707-03-5(Hazardous Substances Data)

Usage

Description

Diphenylphosphinic acid (DPPA, hdpp) is an organophosphinic acid compound characterized by its white fine crystalline solid appearance. It is known for its reactivity and utility in various chemical processes, including its role as a flame-retardant and promoter for palladium catalytic systems. The thermal degradation of DPPA has been studied using thermogravimetric analysis (TGA), and it can engage in reactions with cadmium nitrate to form coordination polymers. Additionally, DPPA can be ortho-lithiated to create mono ortho-functionalized derivatives and biphenyl-2,2′-diylbis(phenylphosphinic acid) through copper-catalyzed coupling.

Uses

Used in Chemical Synthesis:
Diphenylphosphinic acid is used as a reagent for the synthesis of bidentate ligands and peptide coupling agents, contributing to the development of complex organic compounds and pharmaceuticals.
Used in Flame-Retardant Industry:
Diphenylphosphinic acid serves as a reactive flame-retardant, enhancing the fire resistance of materials and providing safety in various applications.
Used in Catalysis:
As a promoter for palladium catalytic systems, DPPA aids in accelerating chemical reactions, which is particularly useful in the fields of organic synthesis and materials science.
Used in Coordination Polymer Formation:
Diphenylphosphinic acid is used in the formation of one-dimensional coordination polymers, such as catena-poly[[bis(dimethylformamide-κO)cadmium(II)]-bis(μ-diphenylphosphinato-κ(2)O:O′)], which have potential applications in catalysis, sensing, and other areas.
Used in Carbonylation Reactions:
DPPA promotes the carbonylation of nitrobenzene and aniline to diphenylurea, a reaction that is important in the production of various chemical intermediates and pharmaceuticals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 1671, 1957 DOI: 10.1021/jo01363a037

Purification Methods

Recrystallise it from 95% EtOH and dry it under vacuum at room temperature. [see Kosolapoff Organophosphorus Compounds J Wiley, NY, 1950, Kosolapoff and Maier Organic Phosphorus Compounds Wiley-Interscience, NY, 1972-1976, Beilstein 16 IV 1036.]

InChI:InChI=1/C12H11O2P/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H,13,14)

Upstream product

• 27325-49-1 1-piperidinylphosphorous dichloride 
• 1498-56-2 piperidin-1-yl-phosphonic acid dichloride 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 644-97-3 Dichlorophenylphosphine 
• 141-52-6 sodium ethanolate 
• 1079-66-9 chloro-diphenylphosphine 
• 811-51-8 sodium thioethylate 
• 762-04-9 phosphonic acid diethyl ester 
• 78-40-0 triethyl phosphate 
• 108-88-3 toluene 
• 829-85-6 diphenylphosphane 
• 288-32-4 1H-imidazole 
• 766-76-7 benzoate 

Downstream Products

• 18593-20-9 bis-(3-nitrophenyl)phosphinic acid 
• 832-39-3 dicyclohexylphosphinic acid 
• 6840-28-4 diphenyl(p-tolyl)phosphine oxide 
• 2959-74-2 benzyldiphenylphosphine oxide 
• 63103-76-4 diphenyl 2-methylpropyl phosphine oxide 
• 13689-20-8 (cyclohexyl)diphenylphosphane oxide 
• 1733-57-9 ethydiphenylphosphine oxide 
• 4233-13-0 butyldiphenylphosphine oxide 
• 1499-21-4 Diphenylphosphinic chloride 
• 114537-02-9 diphenyl-phosphinic acid-(2-dimethylamino-ethyl ester) 
• 33921-16-3 3-(diphenylphosphoryl)propanamide 
• 124340-38-1 diphenylphosphinic acid triethylsilyl ester 
• 102269-12-5 phenylphosphonic diphenylphosphinic anhydride phenyl ester 
• 113893-60-0 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl diphenylphosphinate 

Relevant articles and documents

Proline/pipecolinic acid-promoted copper-catalyzed P-arylation

We have developed a convenient and efficient approach for P-arylation of organophosphorus compounds containing P-H. Using commercially available and inexpensive proline and pipecolinic acid as the ligands greatly improved the efficiency of the coupling reactions, so the method can provide an entry to arylphosphonates, arylphosphinates and arylphosphine oxides.

Solubilities of diphenylphosphinic acid in selected solvents

Diphenylphosphinic acid (DPPA) was synthesized and characterized by infrared spectroscopy (IR), nuclear magnetic resonance (1H NMR), mass spectroscopy (MS), and elemental analysis. The melting point and the enthalpy of fusion of DPPA were measured by a differential scanning calorimeter (DSC), and the thermal stability of DPPA was measured by thermogravimetric analysis (TGA). The solubility data of DPPA in nine solvents were measured and correlated with an empirical equation. The estimated uncertainty of all the solubility values based on error analysis and repeated observations was within 2.0 %.

A 31P-SNP study of the photolysis of (2,4,6-trimethylbenzoyl)diphenylphosphine oxide in micelles of different sizes

31P stimulated nuclear polarization spectra and their dependence on time after photolysis of (2,4,6-trimethylbenzoyl)diphenylphosphine oxide in micellar solution of sodium octyl- (SOS) and dodecylsulfate (SDS) are investigated and discussed in terms of the numerical solution of the stochastic Liouville equation for a microreactor model.The decay of the geminate radical pair is found to be about 2.5 times slower in SDS than in the SOS micelles due to a larger re-encounter rate in the latter one.Simulation of the experimental results further suggests J0= ca. -1.6*1010 rad/s for the exchange interaction at contact distance, and an increasing micellar size with increasing radical size.

DEOXYGENATION OF THE OXIRANE RING IN THE REACTION OF THE DIPHENYLPHOSPHINITE ANION WITH EPICHLOROHYDRIN

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Synthesis, Structure, and Coordination Chemistry of Phosphine-Functionalized Imidazole/Imidazolium Salts and Cleavage of a C-P Bond in an NHC-Phosphenium Salt using a Pd(0) Precursor

A simple method involving metal-halogen exchange reaction(s) to prepare various phosphine-functionalized imidazole/imidazolium salts and their coordination chemistry with different metal precursors has been described. Interestingly, the reaction of 1,3-dimethyl-2-(diphenylphosphino)-4-iodoimidazolium iodide (6) with Pd2(dba)3 in the presence of triphenylphosphine affords a Pd(II)-NHC complex which involves the cleavage of a C-P bond presumably occurring via oxidative addition of Pd(0) to a C-I bond to afford an in situ generated Pd(II) species, which subsequently reacts with another 1 equiv of 6 through the phosphine center to form an adduct followed by a dephosphinylation reaction. (Chemical Equation Presented).

The Catalytic Role of Iodide Ion/Iodine Couple in the Photo-Reduction of 10-Methylacridinium Ion with Diphenylphosphine Oxide

Photo-redox between diphenylphosphine oxide and 10-methylacridinium iodide with visible light in aqueous acetonitrile under argon atmosphere is initiated by single electron transfer from the phosphorus compound to the acridinium salt in the potoexcited state giving diphenylphosphinic acid and 10-methylacridan as the final products.Iodide ion/iodine couple plays a crucial role for transferring an electron in this reaction.

Direct synthesis of α-hydroxyketone phosphates from terminal alkynes and H-phosphine oxides in the presence of PhI(OAc)2and H2O

A simple and highly efficient one-pot method for the construction of α-hydroxyketone phosphates from terminal alkynes and H-phosphine oxides has been developed in the presence of PhI(OAc)2and H2O. The present protocol provides an attractive approach to α-hydroxyketone phosphates in good to high yields, with the advantages of operation simplicity, the use of commercially available materials, broad substrate scope, high atom efficiency and good tolerance to scale-up synthesis.

Phosphinite-phosphine oxide isomerization of diphenylphosphinite derivatives of 1,4:3,6-dianhydro-D-mannitol

Phosphorylation of 1,4:3,6-dianhydro-D-mannitol with diphenylphosphinous chloride provided a bisphosphinite derivative that, unlike what is observed in the phosphorylation with phosphorous chlorides and amides, undergoes fast phosphinite-phosphine oxide isomerization. The monophosphinite derivative, in addition, is strongly dephosphorylated. The effect of the solvents and amines (HCl acceptors) on the phosphinite-phosphine oxide isomerization is studied.

Insertion of phosphinidene complexes into the P-H bond of secondary phosphine oxides: A new version of the phospha-Wittig synthesis of P=C double bonds

Terminal phosphinidene complexes [RP-W(CO)5], as generated at 60 °C in the presence of copper chloride from the appropriate 7-phosphanorbornadiene complexes, react with secondary phosphine oxides Ar2P(O)H to give the insertion products into the P-H bonds. After metalation with NaH, these products react with aldehydes to give the corresponding phosphaalkenes which are trapped by dimethylbutadiene.

Potassium tert -Butoxide Mediated Reductive C-P Cross-Coupling of Arylvinyl Sulfides through C-S Bond Cleavage

A transition-metal-free t -BuOK-mediated reductive C-P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C-S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C-P bond through C-S bond cleavage and reduction of a C-C double bond in one pot.

Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids

An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.