MilliporeSigma
All Photos(1)

287881

Sigma-Aldrich

Diphenylphosphine oxide

97%

Sign Into View Organizational & Contract Pricing

Select a Size

Synonym(s):
HPOPh2
Linear Formula:
(C6H5)2P(O)H
CAS Number:
Molecular Weight:
202.19
MDL number:
PubChem Substance ID:

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

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
252964106496287822
Diphenylphosphine 98%

Sigma-Aldrich

252964

Diphenylphosphine

Tri(o-tolyl)phosphine 97%

Sigma-Aldrich

287822

Tri(o-tolyl)phosphine

form

solid

form

liquid

form

-

form

-

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

reaction suitability

-

reaction suitability

reagent type: ligand
reaction type: C-C Bond Formation, reagent type: ligand
reaction type: Carbonylations, reagent type: ligand
reaction type: Cycloadditions, reagent type: ligand
reaction type: Decarboxylations, reagent type: ligand
reaction type: Diels-Alder Reaction, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

mp

56-57 °C (lit.)

mp

-

mp

137-142 °C (lit.)

mp

123-125 °C (lit.)

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

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

Signal Word

Warning

Hazard Statements

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 4

1 of 4

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
Visible-light-induced organophotoredox-catalyzed phosphonylation of 2 H-indazoles with diphenylphosphine oxide
Singsardar M, et al.
The Journal of Organic Chemistry, 83(20), 12694-12701 (2018)
Alcock, N. W.; Brown, J. M.; Hulmes, D. I.
Tetrahedron Asymmetry, 4, 743-743 (1993)
Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides
Fu Tingting, et al.
Organic & Biomolecular Chemistry, 12(18), 2895-2902 (2014)
Recent progress in the synthesis of phosphorus-containing indole derivatives
Chen L and Zou Y-X
Organic & Biomolecular Chemistry, 16(41), 7544-7556 (2018)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service