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Sigma-Aldrich

Diphenylphosphinic acid

≥98.0% (T)

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About This Item

Linear Formula:
(C6H5)2P(O)OH
CAS Number:
1707-03-5
Molecular Weight:
218.19
Beilstein:
2804567
EC Number:
216-948-5
MDL number:
MFCD00002132
UNSPSC Code:
12352100
PubChem Substance ID:
57650161
NACRES:
NA.22

Assay

≥98.0% (T)

mp

193-195 °C (lit.)
193-196 °C

solubility

0.1 M NaOH: soluble 0.5 g/10 mL, clear, colorless

SMILES string

OP(=O)(c1ccccc1)c2ccccc2

InChI

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

InChI key

BEQVQKJCLJBTKZ-UHFFFAOYSA-N

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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.

Application

Diphenylphosphinic acid is an important starting material for the synthesis of organophosphinic compounds. Diphenylphosphinic acid may be used for the preparation of coordination polymers, via reaction with alkaline earth metal salts in dimethylformamide (DMF) solvent:
  • [Mg3(O2PPh2)6(DMF)2]·2DMF
  • [Ca(O2PPh2)2(DMF)2]
  • [Sr(O2PPh2)2(DMF)2]
  • [Ba(O2PPh2)2(DMF)2]
It may be used for the synthesis of compounds with the Al-O-X (X = Si, P, C) motif, via reaction with LAlH2 (L = HC(CMeNAr)2, Ar = 2,6-iPr2C6H3). It may be employed as a novel co-adsorbent in dye-sensitized solar cells (DSCs) based on nanocrystalline TiO2 sensitized with N719 dye. It may be used in the synthesis of arylindium phosphinate.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Pengfei Hao et al.
Dalton transactions (Cambridge, England : 2003), 41(43), 13520-13524 (2012-09-29)
The reactions of LAlH2 (L = HC(CMeNAr)2, Ar = 2,6-iPr2C6H3) (1) with diphenylsilanediol, phenylphosphonic acid, diphenylphosphinic acid, and pyrocatechol afford compounds with the Al–O–X (X = Si, P, C) motif of composition [LAl(μ-O)]2Si(Ph)2 (2), [LAl(μ-O)]2PO(Ph) (3), LAl[OPO(Ph)2]2 (4), and LAl(μ-O)2(o-C6H4)
Synthesis and structure of three molecular arylindium phosphinates.
Ahmad SU, et al.
Main Group Metal Chemistry, 37(5-6), 163-167 (2014)
Jeffrey A Rood et al.
Acta crystallographica. Section C, Structural chemistry, 70(Pt 11), 1069-1074 (2014-11-06)
Reaction of cadmium nitrate with diphenylphosphinic acid in dimethylformamide solvent yielded the one-dimensional coordination polymer catena-poly[[bis(dimethylformamide-κO)cadmium(II)]-bis(μ-diphenylphosphinato-κ(2)O:O')], [Cd(C12H10O2P)2(C3H7NO)2]n, (I). Addition of 4,4'-bipyridine to the synthesis afforded a two-dimensional extended structure, poly[[(μ-4,4'-bipyridine-κ(2)N:N')bis(μ-diphenylphosphinato-κ(2)O:O')cadmium(II)] dimethylformamide monosolvate], {[Cd(C12H10O2P)2(C10H8N2)]·C3H7NO}n, (II). In (II), the 4,4'-bipyridine molecules link
A novel diphenylphosphinic acid coadsorbent for dye-sensitized solar cell.
Shen H, et al.
Electrochimica Acta, 56(5), 2092-2097 (2011)
Jeffrey A Rood et al.
Acta crystallographica Section B, Structural science, crystal engineering and materials, 70(Pt 3), 602-607 (2014-06-04)
Reaction of alkaline earth metal salts with diphenylphosphinic acid in dimethylformamide solvent afforded four coordination polymers: [Mg3(O2PPh2)6(DMF)2]·2DMF (I), [Ca(O2PPh2)2(DMF)2] (II), [Sr(O2PPh2)2(DMF)2] (III) and [Ba(O2PPh2)2(DMF)2] (IV) (where DMF is N,N-dimethylformamide). Single-crystal X-ray diffraction revealed that all four compounds produce linear chain
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