2310-89-6

Basic information

• Product Name: phenyl hydrogen phosphonate
• Synonyms: phenyl hydrogen phosphonate;Phosphonic acid, monophenyl ester;Phosphonic acid phenyl ester
• CAS NO: 2310-89-6
• Molecular Formula: C₆H₇O₃P
• Molecular Weight: 158.091741
• EINECS: 218-998-3
• Mol File: 2310-89-6.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• CAS DataBase Reference: phenyl hydrogen phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl hydrogen phosphonate(2310-89-6)
• EPA Substance Registry System: phenyl hydrogen phosphonate(2310-89-6)

Safety Data

• Hazardous Substances Data: 2310-89-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Phenyl hydrogen phosphonate is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its reactivity and stability make it a valuable building block for the development of new molecules with desired properties.
Used in Material Science:
In the field of material science, phenyl hydrogen phosphonate is utilized as a precursor for the preparation of phosphonate-based materials, such as self-assembled monolayers, polymers, and coatings. These materials exhibit unique properties, such as enhanced stability, corrosion resistance, and biocompatibility, making them suitable for applications in sensors, electronics, and medical devices.
Used in Environmental Applications:
Phenyl hydrogen phosphonate can be employed as an environmentally friendly alternative to traditional phosphates in various applications, such as water treatment, detergents, and fertilizers. Its ability to form stable complexes with metal ions and its biodegradability contribute to its potential as a sustainable and eco-friendly option.
Used in Analytical Chemistry:
In analytical chemistry, phenyl hydrogen phosphonate serves as a reagent for the detection and quantification of metal ions, particularly transition metals. Its ability to form stable complexes with these ions allows for sensitive and selective analytical methods, such as spectrophotometry, chromatography, and electrochemistry.
Overall, phenyl hydrogen phosphonate is a versatile compound with a wide range of applications across different industries, including chemical synthesis, material science, environmental applications, and analytical chemistry. Its unique properties and reactivity make it a valuable component in the development of new technologies and products.

InChI:InChI=1/C6H7O3P/c7-10(8)9-6-4-2-1-3-5-6/h1-5,10H,(H,7,8)

Upstream product

• 3426-89-9 phenyl phosphorodichloridite 
• 4712-55-4 diphenyl hydrogen phosphite 
• 108-95-2 phenol 
• 15845-66-6 Ethylphosphorige Saeure 
• 101-02-0 triphenyl phosphite 
• 6798-33-0 1-(benzyloxycarbonylamino)-2,2,2-trifluoroethanol 
• 3724-14-9 2-hydroxybenzenesulfonamide 
• 1003-67-4 4-methylpyridine-1-oxide 
• 1184-78-7 trimethylamine-N-oxide 
• 1122-58-3 dmap 
• 1122-96-9 4-methoxypyridine N-oxide 
• 7529-22-8 4-methylmorpholine N-oxide 
• 100-46-9 benzylamine 

Downstream Products

• 1231-03-4 Diphosphorsaeure-P1,P2-diphenylester 
• 4712-55-4 diphenyl hydrogen phosphite 
• 83472-82-6 N-phenylphosphoryl-4-N',N'-dimethylaminopyridinium 
• 59045-84-0 C₁₁H₁₀NO₃P 

Relevant articles and documents

The Synthesis and Mechanistic Considerations of a Series of Ammonium Monosubstituted H-Phosphonate Salts

A series of ammonium monosubstituted H-phosphonate salts were synthesized by combining H-phosphonate diesters with amines in the absence of solvent at 80 °C. Variation of the ester substituent and amine produced a range of ionic liquids with low melting points. The products and by-products were analyzed by spectroscopic and spectrometric techniques in order to get a better mechanistic picture of the dealkylation and formal dearylation observed. For dialkyl H-phosphonate diesters, (RO)2P(O)H (R=alkyl), the reaction proceeds via direct dealkylation with the reactivity increasing in the order R=iPr?1. For the diphenyl H-phosphonate diesters, (PhO)2P(O)H, the dearylation was found to proceed via phenol-assisted formation of a 5-coordinate intermediate, (PhO)3PH(OH), from which P(OPh)3 and water were eliminated. The presence of an equivalent of water then facilitated the formation of P(OH)2OPh and the amine, R'NH2, subsequently abstracted a proton from it to yield [(PhO)PH(O)O]-[R'NH3]+.

31PNMR study on the reactions of amino acids and sugar derivatives with pyrophosphorous acid as a possible prebiotic phosphonylating agent

Phosphorus is an essential element in living organisms. Evaluating prebiotic processes that lead to phosphorylated biomolecules is an important step toward understanding the origin of life. Schreibersite ([Fe,Ni]3P) is a meteoritic phosphorus mineral which releases various phosphorus species reactive toward biomolecules. We studied the reactions between biomolecules and pyrophosphorus acid (H4P2O5), which is a phosphorous acid derivative released from schreibersite. The reactions between pyrophosphorous acid and molecules having hydroxy groups were carried out under mild alkaline conditions. Notably, some biologically important molecules such as L-serine, L-tyrosine, L-threonine, D-ribose, and D-glyceraldehyde reacted with pyrophosphorous acid to give corresponding phosphonates. These results suggested that if schreibersite and the biomolecules co-existed in the prebiotic earth, they formed the phosphonates which were able to play roles as surrogates or precursors of phosphorylated biomolecules.

Catalytic Phosphite Hydrolysis under Neutral Reaction Conditions

Cationic phosphametallocene-based platinum(II) aqua complexes were used as efficient precatalysts for the hydrolysis of aromatic and aliphatic tertiary phosphites under neutral reaction conditions at room temperature, leading to the selective cleavage of one P-O bond of the phosphite. NMR labeling experiments combined with stoichiometric model reactions and theoretical density functional theory calculations, performed with the appropriate model compounds, shed light on the operative catalytic cycle, which comprises intramolecular water molecule transfer to the cis-coordinated phosphite molecule.

Oxyonium phosphobetaines - Unusually stable nucleophilic catalyst-phosphate complexes formed from H-phosphonates and N-oxides

Aryl H-phosphonates react with N-oxides to form previously unknown stable zwitterionic oxyonium phosphates comprising an -O-P-O-N+Z atom system. Their structures were confirmed i.e. by X-ray crystal structure analysis, and some mechanisms were proposed for their formation. Stability during storage and reactivity toward nucleophiles points to their possible synthetic applications.

Organophosphorus chemistry without PCl3: A bridge from hypophosphorous acid to H-phosphonate diesters

A process for the conversion of hypophosphorous acid (H3PO 2, HPA) and alcohols into various H-phosphonate diesters [(RO) 2P(O)H] is described. The new reaction provides a missing bridge between HPA and important H-phosphonates, completely avoiding the use of PCl3. Nickel chloride or nickel on silica catalyze the oxidative phosphorylation of alkyl phosphinates with various alcohols or water. The reaction is atom economic and avoids the formation of waste products. The previous need for both chlorine and base is completely avoided. Esterification of hypophosphorous acid followed by reaction with another molecule of alcohol under the action of a nickel catalyst provides a green method for the preparation of H-phosphonates. This method entirely avoids the need for any stoichiometric chloride unlike those based on phosphorus trichloride. Copyright

Method and compositions for identifying anti-HIV therapeutic compounds

Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.

Method and compositions for identifying anti-HIV therapeutic compounds

Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.

Synthesis of the First Stable Phosphonamide Transition State Analogue

Three methods were selected for the one-pot synthesis of the fully protected β-fluoroaminophosphonic acids, using the readily accessible N-protected β-fluoroaminals. These were activated by acylation leading, by β-elimination, to a transient N-acylimine immediately trapped by reactive forms of dialkyl phosphites. Avoiding basic conditions, the complete or partial deprotection of these N-protected β-fluoroaminophosphonic esters allowed the synthesis of the free amino acids, their esters, and a racemic β-trifluorophosphonamidic acid. The latter, which represents a transition state analogue formed by the bacterial transpeptidase, is perfectly stable at pH 4.7, contrary to the nonfluorinated compounds.

Aryl H-phosphonates. 7. Studies on the formation of phosphorus-carbon bond in the reaction of trityl and benzyl halides with dialkyl and diphenyl H-phosphonates

The reactions of H-phosphonate diesters with trityl and benzyl halides were investigated using 31P NMR spectroscopy. It was found that extensive oxidation, which usually accompanies the formation of trityl- or p-nitrobenzylphosphonates from the corresponding alkyl bromides in the Michaelis-Becker reaction, can be considerably suppressed or completely eliminated by reacting p-nitrobenzyl or trityl bromides with diphenyl H-phosphonate in acetonitrile in the presence of DBU.

Studies on aryl H-phosphonates. 3. Mechanistic investigations related to the disproportionation of diphenyl H-phosphonate under anhydrous basic conditions

Diphenyl H-phosphonate undergoes under anhydrous reaction conditions a base-promoted disproportionation to triphenyl phosphite and phenyl H- phosphonate. On the basis of 31P NMR data the most likely mechanism for this transformation was proposed. In order to substantiate these findings and to get a deeper insight into the chemistry of aryl H-phosphonate esters, we carried out also some studies on activation of phenyl and diphenyl H- phosphonates with various condensing agents. We found that aryl vs alkyl esters of phosphonic acid often follow different reaction pathways during the activation, and this can most likely be traced back to higher electrophilicity of the phosphorus centre and to higher reactivity of the P- H bonds in aryl H-phosphonate derivatives.