CAS 1707-03-5 Diphenylphosphinic acid - Catalysts / Alfa Chemistry

Synonyms

Hydroxydiphenylphosphine Oxide

IUPAC Name

diphenylphosphinic acid

Molecular Weight

218.19

Molecular Formula

C12H11O2P

Canonical SMILES

C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)O;

InChI

BEQVQKJCLJBTKZ-UHFFFAOYSA-N

InChI Key

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)

Boiling Point

194 °C

Melting Point

193-195 °C(lit.)

Purity

98%

Density

1.25±0.1 g/cm3(Predicted)

Appearance

Solid

Storage

Store below +30°C.

Complexity

218

Covalently-Bonded Unit Count

EC Number

216-948-5

Exact Mass

218.05g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Isomeric SMILES

C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)O

Monoisotopic Mass

218.05g/mol

NSC Number

13583

Rotatable Bond Count

Topological Polar Surface Area

37.3A^2

Application

Diphenylphosphinic acid, a white fine crystalline solid and organophosphinic acid compound, serves multiple roles in various chemical applications. It is primarily used as a reagent in the synthesis of bidentate ligands and peptide coupling agents, which are essential in numerous organic synthesis processes. Additionally, it acts as a reactive flame-retardant and is a promoter for palladium catalytic systems, enhancing their effectiveness. The compound has been studied for its thermal degradation using thermogravimetric analysis. It also reacts with cadmium nitrate in dimethylformamide solvent to form a one-dimensional coordination polymer. In further applications, it facilitates the carbonylation of nitrobenzene and aniline into diphenylurea and can be ortho-lithiated to produce mono ortho-functionalized derivatives through electrophilic trapping. Moreover, it partakes in copper-catalyzed coupling to form biphenyl-2,2'-diylbis(phenylphosphinic acid).

February 11, 2025

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