43153
Diphenylphosphinic acid
≥98.0% (T)
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About This Item
Linear Formula:
(C6H5)2P(O)OH
CAS Number:
Molecular Weight:
218.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
216-948-5
Beilstein/REAXYS Number:
2804567
MDL number:
Assay:
≥98.0% (T)
Product Name
Diphenylphosphinic acid, ≥98.0% (T)
InChI key
BEQVQKJCLJBTKZ-UHFFFAOYSA-N
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)
SMILES string
OP(=O)(c1ccccc1)c2ccccc2
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
Quality Level
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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]
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
Thermal kinetics and decomposition mechanism of methylphenylphosphinic acid and diphenylphosphinic acid.
Shao X, et al.
Chemical Research in Chinese Universities, 30(6), 1028-1031 (2014)
Synthesis and structure of three molecular arylindium phosphinates.
Ahmad SU, et al.
Main Group Metal Chemistry, 37(5-6), 163-167 (2014)
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)
The palladium-phenanthroline catalyzed carbonylation of nitroarenes to diarylureas: Effect of chloride and diphenylphosphinic acid.
Gasperini M, et al.
Journal of Organometallic Chemistry, 690(20), 4517-4529 (2005)
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