287881
Diphenylphosphine oxide
97%, solid
Synonym(s):
HPOPh2
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About This Item
Linear Formula:
(C6H5)2P(O)H
CAS Number:
Molecular Weight:
202.19
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
MDL number:
Product Name
Diphenylphosphine oxide, 97%
Quality Level
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:
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Related Content
Phosphine Ligand Application Guide
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
Edwards, M. L.; Stemerick, D. M. et al.
Tetrahedron Letters, 31, 5571-5571 (1990)
Recent progress in the synthesis of phosphorus-containing indole derivatives
Chen L and Zou Y-X
Organic & Biomolecular Chemistry, 16(41), 7544-7556 (2018)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 287881-5G | 04061833321218 |
| 287881-1G | 04061826273272 |