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1707-03-5

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1707-03-5 Usage

Chemical Properties

white fine crystalline solid

Uses

Diphenylphosphinic acid is used as a reagent employed in the synthesis of bidentate ligands and peptide coupling agents.

Synthesis Reference(s)

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

General Description

Diphenylphosphinic acid (DPPA, hdpp) is an organophosphinic acid compound. It finds application as a reactive flame-retardant and promoter for palladium catalytic systems. Thermal degradation of DPPA has been studied by thermogravimetric analysis (TGA) method. DPPA reacts with cadmium nitrate in dimethylformamide solvent to afford the one-dimensional coordination polymer catena-poly[[bis(dimethylformamide-κO)cadmium(II)]-bis(μ-diphenylphosphinato-κ(2)O:O′)]. It has been repoted to promote the carbonylation of nitrobenzene and aniline to diphenylurea. Ortho-lithiated DPPA can form mono ortho-functionalized derivatives by electrophilic trapping and biphenyl-2,2′-diylbis(phenylphosphinic acid) by copper catalyzed coupling.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 1707-03-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,0 and 7 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1707-03:
(6*1)+(5*7)+(4*0)+(3*7)+(2*0)+(1*3)=65
65 % 10 = 5
So 1707-03-5 is a valid CAS Registry Number.
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)

1707-03-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11563)  Diphenylphosphinic acid, 99%   

  • 1707-03-5

  • 5g

  • 366.0CNY

  • Detail
  • Alfa Aesar

  • (A11563)  Diphenylphosphinic acid, 99%   

  • 1707-03-5

  • 25g

  • 942.0CNY

  • Detail
  • Alfa Aesar

  • (A11563)  Diphenylphosphinic acid, 99%   

  • 1707-03-5

  • 100g

  • 3350.0CNY

  • Detail
  • Aldrich

  • (43153)  Diphenylphosphinicacid  ≥98.0% (T)

  • 1707-03-5

  • 43153-5G

  • 252.72CNY

  • Detail

1707-03-5Relevant articles and documents

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

Huang, Cheng,Tang, Xu,Fu, Hua,Jiang, Yuyang,Zhao, Yufen

, p. 5020 - 5022 (2006)

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

Zhang, Gai-Qing,Wang, Li-Sheng,Fan, Rui-Lan,Shao, Xian-Zhao,Wang, Xiao-Fang

, p. 1192 - 1195 (2008)

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

Ananchenko, G. S.,Bagryanskaya, E. G.,Tarasov, V. F.,Sagdeev, R. Z.,Paul, H.

, p. 267 - 273 (1996)

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

Antoshin, A. E.,Kharitonov, A. V.,Tsvetkov, E. N.

, p. 2448 (1987)

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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

Karthik, Vedhagiri,Gupta, Vivek,Anantharaman, Ganapathi

, p. 3713 - 3720 (2015)

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

Yasui, Shinro,Shioji, Kosei,Ohno, Atsuyoshi,Yoshihara, Masakuni

, p. 1393 - 1396 (1993)

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

Hu, Dong-Yan,Li, Meng-Shun,Zhong, Wen-Wu,Ji, Jian-Xin,Zhu, Jin,Wei, Wei,Zhang, Qiang,Cheng, Ming

, p. 1691 - 1695 (2016)

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

Kurochkina,Soboleva,Vasyanina,Grachev,Nifant'ev

, p. 49 - 52 (2005)

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

Hao, Yanwei,Wu, Di,Tian, Rongqiang,Duan, Zheng,Mathey, Fran?ois

, p. 891 - 893 (2016)

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

Feng, Jie,Zhang, Qiaoling,Li, Fuhai,Yang, Lu,Kuchukulla, Ratnakar Reddy,Zeng, Qingle

, p. 224 - 228 (2020/10/30)

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.

Temporary (P=O) directing group enabled carbazoleorthoarylationviapalladium catalysis

Qi, Zhi-Chao,Lou, Qin-Xin,Niu, Yuan,Yang, Shang-Dong

, p. 2021 - 2024 (2021/03/01)

A palladium-catalyzed, temporary P(O) directing group assisted C-H bond arylation of carbazoles was achieved. The release of the directing group occurs spontaneously in the reaction and the mechanistic studies indicate that acid is essential for N-P bond cleavage.

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