1779-48-2

Basic information

• Product Name: Phenylphosphinic acid
• Synonyms: BENZENEPHOSPHINIC ACID;BENZENEPHOSPHONOUS ACID;PHENYLPHOSPHINIC ACID;PHENYLPHOSPHONOUS ACID;Benzolphosphonigsαure;Hydroxyphenylphosphine oxide;hydroxyphenylphosphineoxide;NSC2670
• CAS NO: 1779-48-2
• Molecular Formula: C₆H₇O₂P
• Molecular Weight: 142.09
• EINECS: 217-217-3
• Product Categories: AcidsOrganic Building Blocks;Electronic Chemicals;Micro/Nanoelectronics;Phosphonic/Phosphinic Acids;Phosphorus Compounds;organophosphorus compound;Acids;Building Blocks;Chemical Synthesis;Electronic Chemicals;Materials Science;Organic Building Blocks;Phosphonic/Phosphinic Acids;Phosphorus Compounds
• Mol File: 1779-48-2.mol

Chemical Properties

• Melting Point: 83-85 °C(lit.)
• Boiling Point: 180 °C
• Flash Point: 126.231 °C
• Appearance: White/Crystalline Solid
• Density: 1.376
• Vapor Pressure: 0.001mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Water (Slightly, Heated)
• PKA: pK1:2.1 (17°C)
• Water Solubility: 7.7 g/100 mL (25 ºC)
• BRN: 2802244
• CAS DataBase Reference: Phenylphosphinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylphosphinic acid(1779-48-2)
• EPA Substance Registry System: Phenylphosphinic acid(1779-48-2)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22-34-41-37/38
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• RTECS: SZ5462500
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1779-48-2(Hazardous Substances Data)

Usage

Uses

1. Antioxidant Applications:
Phenylphosphinic acid is used as an antioxidant, providing protection against oxidative stress and damage in various chemical processes and industrial applications.
2. Intermediate for Metallic-Salt Formation:
Phenylphosphinic acid serves as an intermediate in the formation of metallic salts, which are essential in the production of various chemical compounds and materials.
3. Accelerator for Organic Peroxide Catalysts:
Phenylphosphinic acid is used as an accelerator for organic peroxide catalysts, enhancing the efficiency and speed of chemical reactions in the synthesis of various products.
4. Biochemical Marker in Medical Research:
Used in Medical Research:
Phenylphosphinic acid is used as an intermediate in the synthesis of Coproporphyrin I-15N4, which is a vital component in the production of Coproporphyrin I-15N4 Sodium Bisulfate Salt. Phenylphosphinic acid serves as a biochemical marker for distinguishing familial and sporadic porphyria cutanea tarda, as well as a biomarker of environmental toxicity and susceptibility in autism.
5. Environmental Applications:
Phenylphosphinic acid is used in environmental applications as a biomarker to assess the level of toxicity and susceptibility in various ecosystems, contributing to the understanding and management of environmental health.

Purification Methods

Crystallise it from H2O (solubility is 7.7% at 25o). Also purify it by placing the solid in a flask covered with dry Et2O, and allowed it to stand for 1day with intermittent shaking. Et2O is decanted off and the process repeated. After filtration, excess Et2O is removed in a vacuum. It has also been recrystallised from *C6H6. [Michaelis Justus Liebigs Ann Chem 181 265 1876, Banks & Skoog Anal Chem 29 109 1957, NMR: Van Wazer et al. J Am Chem Soc 78 5715 1956, Beilstein 16 IV 1033.]

InChI:InChI=1/C6H7O2P/c7-9(8)6-4-2-1-3-5-6/h1-5,9H,(H,7,8)

Upstream product

• 64-17-5 ethanol 
• 100-34-5 benzene diazonium chloride 
• 644-97-3 Dichlorophenylphosphine 
• 100-63-0 phenylhydrazine 
• 638-21-1 phenylphosphane 
• 23588-02-5 ethyl phenylphosphonochloridothioite 
• 18869-04-0 meso-1,2-Diphenyl-1,2-dibromodiphosphane 
• 108-94-1 cyclohexanone 
• 142506-69-2 3-Phenylphosphinoylsulfanyl-propionic acid ethyl ester 
• 142506-66-9 2-Phenyl-[1,3,2]dithiaphospholane-4,5-dicarboxylic acid diethyl ester 
• 55499-33-7 2,4,5-triphenyl-1,3,2,4,5-dithiatriphospholane 4-sulfide 
• 7732-18-5 water 
• 67-66-3 chloroform 
• 1073-47-8 phenyldibromophosphine 

Downstream Products

• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 1571-33-1 phenylphosphonate 
• 5337-19-9 (m-nitrophenyl)phosphonic acid 
• 638-21-1 phenylphosphane 
• 812-00-0 methylphosphate 
• 71-43-2 benzene 
• 46374-04-3 morpholin-4-yl-phenyl-phosphinic acid 
• 6911-99-5 n-propyl phenyl-H-phosphinate 
• 63007-86-3 Phenylphosphonigsaeure-bis(trimethylsilylester) 
• 172487-18-2 ethyl Phenylphosphinate 
• 14406-31-6 phenyl(carboxymethyl)phosphinate 
• 27262-80-2 Phenylphosphonigsaeuremono(trimethylsilylester) 
• 14530-47-3 dimethylammonium hydrogen diphenylphosphonate 
• 1104-52-5 tetraphenyl-cyclotetraphosphane 

Relevant articles and documents

New dinuclear nickel(II) complexes: Synthesis, structure, electrochemical, and magnetic properties

The reaction of [NiBr2(bpy)2] (bpy = 2,2′-bipyridine) with organic phosphinic acids ArP(O)(OH)H [Ar = Ph, 2,4,6-trimethylphenyl (Mes), 9-anthryl (Ant)] leads to the formation of binuclear nickel(II) complexes with bridging ArP(H)Osu

Synthesis and evaluation of phosphorus containing, specific CDK9/CycT1 inhibitors

Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.

Phosphonothioate hydrolysis by molybdocene dichlorides: Importance of metal interaction with the sulfur of the thiolate leaving group

The metallocene bis(cyclopentadienyl)molybdenum(IV) dichloride Cp 2MoCl2 hydrolyzes O,S-diethyl phenylphosphonothioate (1) with only P-S scission to yield a phosphonate under mild aqueous conditions. In terms of degrading phosphonoth

Revisited synthesis of aryl-H-phosphinates

A systematic study of the reaction conditions for the preparation of pure aryl-H-phosphinate esters, originally developed by Sander and optimized by Petnehazy, is reported. The influence of the reaction concentration has been investigated for the formation of phosphonite intermediates via direct addition of triethyl phosphite to the appropriate Grignard reagent. Subsequent hydrolysis of the phosphonites under acidic conditions gives various aryl-H-phosphinates in high yields and purities. Georg Thieme Verlag Stuttgart, New York.

Efficient synthesis of mono- and diarylphosphinic acids: a microwave-assisted palladium-catalyzed cross-coupling of aryl halides with phosphinate

A general, efficient method for the microwave-assisted synthesis of mono- and diarylphosphinic acids from anilinium phosphinate and aryl halides, using Pd(0) and Xantphos as a supporting ligand, was developed.

Proline/pipecolinic acid-promoted copper-catalyzed P-arylation

We have developed a convenient and efficient approach for P-arylation of organophosphorus compounds containing P-H. Using commercially available and inexpensive proline and pipecolinic acid as the ligands greatly improved the efficiency of the coupling reactions, so the method can provide an entry to arylphosphonates, arylphosphinates and arylphosphine oxides.

A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester

A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.

Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds

This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.

Conversions of 2-phenyl-1,3,2-dioxaphospholane under the action of hydrogen chloride

The reaction of 2-phenyl-1,3,2-dioxaphospholane with HCl gives a mixture of phenylphosphinic acid, bis(2-chloroethyl) phenylphosphonate, and phenylphosphine; therewith, intermediate oligomeric phosphonites, hydrophosphoryl compounds, and phosphoranes were detected. Thermal treatment of the reaction mixture results in formation of ethylene phenylphosphonate and (2-chloroethyl)phenylphosphinate.