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Sigma-Aldrich

Diphenylphosphine oxide

97%

Synonym(s):

HPOPh2

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About This Item

Linear Formula:
(C6H5)2P(O)H
CAS Number:
4559-70-0
Molecular Weight:
202.19
MDL number:
MFCD00002079
UNSPSC Code:
12352002
PubChem Substance ID:
24857300
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Hydrophosphonylations
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

56-57 °C (lit.)

functional group

phosphine

SMILES string

O=[PH](c1ccccc1)c2ccccc2

InChI

1S/C12H11OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H

InChI key

ASUOLLHGALPRFK-UHFFFAOYSA-N

Application

Diphenylphosphine oxide can be used as a coupling partner to prepare various organophosphorus compounds via cross-coupling reaction with aryl halides in the presence of Ni/Zn catalyst.
It can also be used as a reactant to synthesize:
  • Diphenyl(2-phenyl-2H-indazol-3-yl)phosphine oxide derivatives by phosphonylation of 2H-indazoles using rose bengal as a catalyst.
  • Alkenyldiphenylphosphine oxides by hydrophosphinylation of terminal alkynes in the presence of transition metal catalysts.
  • Diphenylphosphino-containing chiral ligands for asymmetric catalytic reactions via Pd-catalyzed coupling reaction with aryl triflates.
  • Triarylphosphine oxides and Horner-Wittig reagents.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Facile synthesis of chelating bisphosphine oxides and bisphosphines via palladium-catalyzed bishydrophosphinylation reactions
Allen Jr A, et al.
Tetrahedron Letters, 43(20), 3707-3710 (2002)
Li-Biao Han et al.
Journal of the American Chemical Society, 126(16), 5080-5081 (2004-04-22)
The cheap nickel catalysts are more reactive than the corresponding noble metal catalysts in the catalytic additions of a variety of P(O)-H bonds and an S-H bond to alkynes, affording regio- and stereoselectively both the Markovnikov and the anti-Markovnikov adducts
Recent progress in the synthesis of phosphorus-containing indole derivatives
Chen L and Zou Y-X
Organic & Biomolecular Chemistry, 16(41), 7544-7556 (2018)
Edwards, M. L.; Stemerick, D. M. et al.
Tetrahedron Letters, 31, 5571-5571 (1990)
Alcock, N. W.; Brown, J. M.; Hulmes, D. I.
Tetrahedron Asymmetry, 4, 743-743 (1993)
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