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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
Pricing and availability is not currently available.

Quality Level

100

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

Related Categories

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.[1]
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.[2]
  • Alkenyldiphenylphosphine oxides by hydrophosphinylation of terminal alkynes in the presence of transition metal catalysts.[3][4]
  • Diphenylphosphino-containing chiral ligands for asymmetric catalytic reactions via Pd-catalyzed coupling reaction with aryl triflates.[4]
  • Triarylphosphine oxides and Horner-Wittig reagents.[5][6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ5025
STBD5835V
01830PH
S34159
08601TD

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Diphenylphosphine Oxide
Jeffrey OS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2007)
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)
Kurz, L.; Lee, G.; Morgans, D. et al.
Tetrahedron Letters, 31, 632-632 (1990)
Ni (II)/Zn catalyzed reductive coupling of aryl halides with diphenylphosphine oxide in water
Zhang X, et al.
Organic Letters, 13(13), 3478-3481 (2011)
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
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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