4559-70-0

Basic information

• Product Name: Diphenylphosphine oxide
• Synonyms: Diphenylphosphinoxid;Diphenylphosphonousacid;Diphenylphosphineoxide,97%;Diphenylphosphine oxide 97%;Two phenylphosphate oxygen;Phosphine oxide,diphenyl-;DPPO;HPOPh2
• CAS NO: 4559-70-0
• Molecular Formula: C₁₂H₁₁OP
• Molecular Weight: 202.19
• EINECS: 1312995-182-4
• Product Categories: Pharmaceutical Intermediates;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;Achiral Phosphine;Aryl Phosphine
• Mol File: 4559-70-0.mol

Chemical Properties

• Melting Point: 56-57 °C(lit.)
• Boiling Point: 102-105°C 0,2mm
• Flash Point: 152.905 °C
• Appearance: Yellow to light orange/Crystals
• Refractive Index: 1.608-1.61
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Diphenylphosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenylphosphine oxide(4559-70-0)
• EPA Substance Registry System: Diphenylphosphine oxide(4559-70-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 2
• Hazardous Substances Data: 4559-70-0(Hazardous Substances Data)

Usage

Uses

Diphenylphosphine oxide is used as a versatile reagent and ligand in the field of organic chemistry for several reasons:
1. Used in the Suzuki Reaction:
Diphenylphosphine oxide serves as a crucial component in the Suzuki reaction, a widely employed cross-coupling reaction between an organoboron compound and an organohalide to form new carbon-carbon bonds. Its role in this reaction enhances the efficiency and selectivity of the process.
2. Used in the Preparation of Triarylphosphine Oxides:
Diphenylphosphine oxide is utilized as a starting material or intermediate in the synthesis of various triarylphosphine oxides, which are valuable compounds with applications in different areas, including pharmaceuticals and materials science.
3. Used as Asymmetric Catalysts:
Due to its unique steric and electronic properties, diphenylphosphine oxide is employed as an asymmetric catalyst in various enantioselective reactions. These reactions are essential for the production of chiral molecules with specific configurations, which are vital in the pharmaceutical industry.
4. Used in the Preparation of Alkenyldiphenylphosphine Oxides:
Diphenylphosphine oxide is also used in the synthesis of alkenyldiphenylphosphine oxides, which are important intermediates in the preparation of various complex organic molecules and have potential applications in the development of new drugs and materials.
5. Used in the Preparation of Horner-Wittig Reagents:
Diphenylphosphine oxide is involved in the preparation of Horner-Wittig reagents, which are widely used in the synthesis of alkenes and other valuable organic compounds.
6. Used as a Ligand in Buchwald-Hartwig Cross Coupling Reaction:
Diphenylphosphine oxide acts as a ligand in the Buchwald-Hartwig cross-coupling reaction, a powerful method for the formation of carbon-nitrogen bonds. Its presence in the reaction improves the efficiency and selectivity of the process, making it a valuable tool in the synthesis of various organic compounds, including pharmaceuticals and natural products.
7. Used in Hydrophosphonylations:
Diphenylphosphine oxide is also employed in hydrophobic phosphorylations, a class of reactions that involve the introduction of a phosphoryl group into a molecule. These reactions are essential for the synthesis of various organophosphorus compounds with potential applications in the agrochemical, pharmaceutical, and materials industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 45, p. 165, 1923 DOI: 10.1021/ja01654a024

InChI:InChI=1/C12H10OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H/q+1

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 762-04-9 phosphonic acid diethyl ester 
• 1707-03-5 diphenyl-phosphinic acid 
• 41006-23-9 P,P'-tetraphenyl-oxalic acid diphosphide 
• 96302-92-0 (E)-5-diphenylphosphinoyl-4-methyldec-3-en-2-one 
• 89243-90-3 1,8-Bis(dimethylphosphoryl)-1,8-bis(diphenylphosphoryl)-1,8-octandiol 
• 89243-87-8 1,1,6,6-Tetrakis(diphenylphosphoryl)-1,6-hexandiol 
• 84675-00-3 C₁₃H₁₃O₃PS 
• 84674-97-5 C₁₃H₁₃O₄PS 
• 463-49-0 1,2-propanediene 
• 829-85-6 diphenylphosphane 
• 84322-81-6 3-Diphenylphosphinyl-1-phenyltriazen 
• 71-43-2 benzene 
• 84322-82-7 3-Diphenylphosphinyl-3-methyl-1-phenyltriazen 

Downstream Products

• 1499-21-4 Diphenylphosphinic chloride 
• 1707-03-5 diphenyl-phosphinic acid 
• 27384-09-4 diphenyl(acetyl)phosphine oxide 
• 18629-56-6 1,1-bis(diphenylphosphinoyl)ethanol 
• 18108-02-6 (α-Fluorsulfonylaminobenzyl)-diphenylphosphinoxid 
• 7067-73-4 N-phenyl(diphenylphosphinoyl)formamide 
• 24536-64-9 1-(diphenylphosphoryl)-N-phenylmethanethioamide 
• 25419-99-2 (dimethylamino)(diphenylphosphinoyl)methoxymethane 
• 38563-52-9 1,2-Bis(diphenylphosphinyl)ethylidenimin 
• 33313-44-9 2-(Diphenylphosphinyl)milchsaeure 
• 53144-71-1 4-methylphenylmethyl diphenylphosphine oxide 
• 13683-05-1 bis(diphenylphosphineoxy)dimethylsilane 
• 21416-24-0 1-Diphenylphosphinoyl-1-diphenylphosphinoyloxyaethan 
• 5032-67-7 3-(diphenylphosphinyl)propanenitrile 

Relevant articles and documents

An expedient access to γ-ketophosphine chalcogenides via the chemo-and regioselective addition of secondary phosphine chalcogenides to β,γ-ethylenic ketones

γ-Ketophosphine chalcogenides, precursors for plethora of novel functionalized phosphine chalcogenides and phosphines, are synthesized by chemo-and regioselective addition of secondary phosphine chalcogenides to β,γ-ethylenic ketones under catalyst-and so

5,5'-Diamino-BIPHEP ligands bearing small selector units for non-covalent binding of chiral analytes in solution

A dynamic axially chiral BIPHEP-ligand with 3,5-dichlorobenzoyl amide selector units for non-covalent binding of phenylalanine derivatives has been developed. Interaction studies in solution were performed with rhodium(i) complexes under exclusion of the metal being involved in binding. (Rax, SPhe) and (Sax, SPhe) adducts were observed as significantly separated species in NMR spectroscopy.

Metal-Free, Visible Light-Photocatalyzed Synthesis of Benzo[b]phosphole Oxides: Synthetic and Mechanistic Investigations

Highly functionalized benzo[b]phosphole oxides were synthesized from reactions of arylphosphine oxides with alkynes under photocatalytic conditions by using eosin Y as the catalyst and N-ethoxy-2-methylpyridinium tetrafluoroborate as the oxidant. The reac

Cycloadditions of 3,4-dihydro-2H-pyrrole N-oxide with thioketones and a selenoketone

Cycloadditions of 2-diphenylphosphinoyl-2-methyl-3,4-dihydro-2H-pyrrole N-oxide (DPhPMPO), 3,4-dihydro-2H-pyrrole N-oxide having a diphenylphosphinoyl group at the C2 position with thioketones afforded the corresponding 1,4,2-oxathiazolidines. Dissociation constants of these 5-membered ring products were determined. The cycloadducts were stabilized by the diphenylphosphinoyl group. The reaction of DPhPMPO with di-tert-butyl selenoketone gave the corresponding selenoamide under microwave irradiation. The formation of the selenoamide indicated that the cycloaddition of DPhPMPO with the selenoketone analogue also proceeded through the formation of the corresponding 5-membered ring product.

Extraction and coordination behavior of diphenyl hydrogen phosphine oxide towards actinides

Extraction behavior of some selected actinides like U(VI), Th(IV), and Am(III) was investigated with three different H-phosphine oxides, viz. diphenyl hydrogen phosphine oxide (DPhPO), dihexyl hydrogen phosphine oxide (DHePO) and diphenyl phosphite (DPP).

Conversion of α‐hydroxy(2,4,6‐trimethylbenzyl)diphenylphosphine oxide to TPO: oxidation vs decomposition

This study details the oxidation of α-hydroxy(2,4,6-trimethylbenzyl)diphenylphosphine oxide (α-HDPO) to diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) by choosing the proper MnO2 as oxidant. In addition, the equilibrium of α-HDPO and 2,4

Photochemistry and Photophysics of (1-Naphthoyl)diphenylphosphine Oxide

(l-Naphthoyl)diphenylphosphine oxide (1) was synthesized and characterized and its photochemistry investigated using emission spectroscopy, pulse radiolysis, and nanosecond laser flash photolysis. Fluorescence quantum yields are low in aprotic polar and nonpolar solvents. In methanol, as a result of hydrogen-bonding, change of S1 from an n,π* state to a π,π* state leads to the decrease in the rate constant for intersystem crossing and results, finally, in an increase in fluorescence. Preferential solvation was evaluated using the ET indicator "Reichardt's dye" (RD). ETN values were determined by gradually increasing the concentrations of methanol in methanol/acetonitrile mixtures. Fluorescence quantum yields correlate with the ETN values. Photolysis of 1 yields diphenyl[l-naphthoyl)oxy]phosphine (6), formed mainly via cage recombination of radicals. No radicals were detected by either nanosecond laser flash photolysis or pulse radiolysis of 1 in aprotic solvents. However, photolysis in methanol yields radicals when 1 is excited at 266 nm. The phosphinoyl radical can be quenched by either methyl methacrylate (MMA) or oxygen (kq = 5.0 × 107 and 5.3 × 108 M-1 s-1, respectively). Such radical generation most likely results from the singlet excited state.

Synthesis of novel N,O-macrocyclic ligands, functionalized by phosphine oxide groups

[Figure not available: see fulltext.] As a result of the implementation of two approaches, the Pudovik reaction (the reaction of macrocyclic azomethines with secondary phosphine oxides) and the Kabachnik–Fields reaction (three-component one-pot process involving dialdehydes, diamines, and secondary phosphine oxides), novel N,O-containing macrocyclic ligands with phosphine oxide groups were first obtained. The synthesized macrocycles are a kind of α-aminophosphoryl compounds that can be used in the synthesis of supramolecular systems.

Phosphinoyl radicals: Structure and reactivity. A laser flash photolysis and time-resolved ESR investigation

The photochemistry of a series of bis(acyl)phosphine oxides and the rate constants of the reactions of their phosphorus radicals with n-butylacrylate, thiophenol, bromotrichloromethane, oxygen, and methyl viologen have been investigated by laser flash pho

Rh-Catalyzed Regio- and Enantioselective Allylic Phosphinylation

Transition-metal-catalyzed branched and enantioselective allylic substitution of monosubstituted precursors with carbon, nitrogen, oxygen, sulfur, and fluoride nucleophiles has been well-established. However, such a selective carbon-phosphorus bond formation has not been realized probably due to the catalyst deactivation by the strong coordinating nature of phosphinylating reagents. Herein, we report a Rh-catalyzed highly regio- and enantioselective synthesis of allylic phosphine oxides in the presence of a chiral bisoxazoline-phosphine ligand. The application of α-hydroxylalkylphosphine oxides to keep the low concentration of the secondary phosphine oxides is essential for the high yields. The addition of diphenyl phosphoric acid was found to not only activate allylic alcohols but also accelerate the carbon-phosphorus bond formation.