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
• Article Data: 130

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

Description

Diphenylphosphine oxide is an organic compound with the chemical formula (C6H5)2P(O)H, featuring a phosphorus atom bonded to two phenyl groups and a hydroxyl group. It is known for its yellow to light orange crystalline appearance and is widely utilized in various chemical reactions and processes due to its unique properties.

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

• 762-04-9 phosphonic acid diethyl ester 
• 1707-03-5 diphenyl-phosphinic acid 
• 41006-23-9 P,P'-tetraphenyl-oxalic acid diphosphide 
• 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 
• 84322-83-8 1-Diphenylphosphinyl-3-methyl-3-phenyltriazen 
• 1499-21-4 Diphenylphosphinic chloride 
• 12771-59-4 diphenylphosphinoyl radical 
• 75980-60-8 (2,4,6-trimethylbenzoyl)diphenylphosphine oxide 
• 67-56-1 methanol 
• 134920-71-1 1-Diphenylphosphinoxy-1-phenylethan 

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

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

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).

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.

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

Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium

We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani

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.

AlCl3-catalyzed C-H p hosphination of benzene: A mechanistic study

The characteristics of the reaction for the preparation of dichlorophenylphosphine (DCPP) via benzene and PCl3 in the presence of AlCl3 were studied. Some unique characteristics were observed when a catalytic amount of AlCl3 was used. Namely, more than one mole of DCPP was obtained per mole AlCl3, the reaction solution was layered, and DCPP could be directly separated. Our mechanistic study showed that benzene reacted with PCl3 to form DCPP-AlCl3, and DCPP-AlCl3 dissociated into DCPP and AlCl3, continuing to catalyze this reaction. This resulted in the high catalytic efficiency of AlCl3. The layering of the reaction solution was caused by the immiscibility of DCPP-AlCl3 with the raw materials, greatly facilitating the dissociation process of DCPP-AlCl3. The formation of diphenylphosphorus chloride (DPC) was due to a continuous Friedel-Crafts reaction between DCPP and benzene. DPC cooperated with AlCl3 to form the stable coordination compound DPC-AlCl3 that did not dissociate and was responsible for the deactivation of AlCl3.