287881

Sigma-Aldrich

Diphenylphosphine oxide

97%

Synonym(s):
HPOPh2
Linear Formula:
(C6H5)2P(O)H
CAS Number:
Molecular Weight:
202.19
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

97%

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

Packaging

1, 5 g in glass bottle

Application

Use as preparation of triarylphosphine oxides, and as asymmetric catalysts; preparation of alkenyldiphenylphosphine oxides, and Horner-Wittig reagents.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Alcock, N. W.; Brown, J. M.; Hulmes, D. I.
Tetrahedron Asymmetry, 4, 743-743 (1993)
Edwards, M. L.; Stemerick, D. M. et al.
Tetrahedron Letters, 31, 5571-5571 (1990)
Li-Biao Han et al.
Organic letters, 7(14), 2909-2911 (2005-07-01)
[reaction: see text] Diphenylphosphine oxide and related P(O)H compounds react with propargyl alcohols at room temperature in the presence of a catalytic amount of Ni(0) complex and Ph(2)P(O)OH to produce high yields of phosphinoyl 1,3-dienes though an efficient in situ...
Kurz, L.; Lee, G.; Morgans, D. et al.
Tetrahedron Letters, 31, 632-632 (1990)

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