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
• Article Data: 12

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

Definition

ChEBI: An aryl phosphate resulting from the formal condensation of phosphonic acid with 1 mol eq. of phenol

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

Downstream Products

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

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]+.

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.

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