10088-45-6

Basic information

• Product Name: Phenylphosphonic acid methyl ester
• Synonyms: Phenylphosphonic acid hydrogen methyl ester;Phenylphosphonic acid methyl ester
• CAS NO: 10088-45-6
• Molecular Formula: C₇H₉O₃P
• Molecular Weight: 172.1183
• Mol File: 10088-45-6.mol

Chemical Properties

• Melting Point: 91 °C
• Boiling Point: 280.3°Cat760mmHg
• Flash Point: 123.3°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0.00181mmHg at 25°C
• Refractive Index: 1.519
• PKA: 2.18±0.58(Predicted)
• CAS DataBase Reference: Phenylphosphonic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylphosphonic acid methyl ester(10088-45-6)
• EPA Substance Registry System: Phenylphosphonic acid methyl ester(10088-45-6)

Safety Data

• Hazardous Substances Data: 10088-45-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Phenylphosphonic acid methyl ester is used as a chemical intermediate for the production of herbicides, flame retardants, and pharmaceuticals. Its unique properties allow it to be a key component in the synthesis of these products, contributing to their effectiveness and performance.
Used in Organic Synthesis Processes:
In the field of organic synthesis, Phenylphosphonic acid methyl ester is utilized as a catalyst and stabilizer. Its ability to accelerate chemical reactions and enhance the stability of intermediates makes it a valuable asset in the development of new compounds and materials.
Used in Herbicide Production:
Phenylphosphonic acid methyl ester is used as a key ingredient in the formulation of herbicides. Its incorporation into these products enhances their effectiveness in controlling and eliminating unwanted plant growth, making it a vital component in agricultural and horticultural applications.
Used in Flame Retardant Manufacturing:
This organophosphorus compound is also employed in the production of flame retardants. Its presence in these formulations helps to slow down the spread of fire, providing an essential safety feature in various industries, including construction, textiles, and electronics.
Used in Pharmaceutical Development:
Phenylphosphonic acid methyl ester plays a significant role in the development of pharmaceuticals. Its unique chemical properties make it a valuable intermediate in the synthesis of various drugs, contributing to the advancement of medical treatments and therapies.

InChI:InChI=1/C7H9O3P/c1-10-11(8,9)7-5-3-2-4-6-7/h2-6H,1H3,(H,8,9)

Upstream product

• 58816-54-9 1-(methoxy-phenyl-phosphinoyl)-5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 67-56-1 methanol 
• 57156-84-0 2,4,6-triphenyl-1,3,5-trioxa-3,4,6-triphosphinane-2,4,6-trioxide 
• 63581-54-4 hydrogen methyl phenylphosphonate 
• 80642-96-2 C₆H₇O₆PS*2H₃N 
• 42976-67-0 O-methyl phenylphosphonothioic acid 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 146849-38-9 benzylmethyl phenylphosphonate 
• 18106-76-8 methyl benzoyl(phenyl)phosphinate 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 69813-38-3 2-phenyl-5,6-dehydro-1,3,2-dioxaphosphepane 
• 644-97-3 Dichlorophenylphosphine 
• 121-70-0 phenylphosphonous acid 
• 3497-00-5 phenylthiophosphonic acid dichloride 

Downstream Products

• 94274-44-9 tert-Butylammonium-methyl- 
• 2240-41-7 dimethyl phenylphosphonate 
• 167955-25-1 Methyl phenylpyrophosphonate 
• 58816-57-2 O-Methyl-O-β-hydroxyaethyl-phenylphosphonat 

Relevant articles and documents

Wet and dry processes for the selective transformation of phosphonates to phosphonic acids catalyzed by br?nsted acids

A "wet"process and two "dry"processes for converting phosphonate esters to phosphonic acids catalyzed by a Bronsted acid have been developed. Thus, in the presence of water, a range of alkyl-, alkenyl-, and aryl-substituted phosphonates can be generally hydrolyzed to the corresponding phosphonic acids in good yields catalyzed by trifluoromethyl sulfonic acid (TfOH) at 140 °C (the wet process). On the other hand, with specific substituents of the phosphonate esters, the conversion to the corresponding phosphonic acids can be achieved under milder conditions in the absence of water (the dry process). Thus, the conversion of dibenzyl phosphonates to the corresponding phosphonic acids took place smoothly at 80 °C in toluene or benzene in high yields. Moreover, selective conversion of benzyl phosphonates RP(O)(OR′)(OBn) to the corresponding mono phosphonic acids RP(O)(OR′)(OH) can also be achieved under the reaction conditions. The dealkylation via the generation of isobutene of ditert- butyl phosphonate, and the related catalysis by TfOH took place even at room temperature to give the corresponding phosphonic acids in good to high yields. Nafion also shows high catalytic activity for these reactions. By using Nafion as the catalyst, phosphonic acids could be easily prepared on a large scale via a simple process.

Regioselective formation of a 2,3-oxaphosphabicyclo[2.2.2] octene 3-oxide in baeyer-villiger type oxidation; a dual pathway for its fragmentation

The O-insertion reaction of a 7-phosphanorbornene (3) unsubstituted on the double-bond gave the corresponding 2,3-oxaphosphabicyclo-[2.2.2]octene oxide (4a) in a regioselective manner that was useful in the fragmentation-related phosphonylation of alcohol

Competition of methanol and tert-butanol in nucleophilic substitution at phosphorus atom

2,3-Oxaphosphabicyclo[2.2.2]octene 1 reacts with alcohols simultaneously according to two competitive mechanisms: bimolecular addition-elimination and unimolecular elimination-addition with the intermediacy of metaphosphonate Ph-PO2 (2). In 1,2-dichloroet

METHOD FOR PRODUCING PHOSPHONIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for producing a phosphonic acid derivative, in which the reaction proceeds under relatively mild reaction conditions without using hydrogen halide or a metal catalyst. SOLUTION: Provided is a method for producing a phosphonic acid derivative represented by formula (1), comprising a step in which an ester group-containing phosphonic acid derivative is reacted in a solvent or without a solvent in the presence of a superacid catalyst. (In formula (1), R1 and R2 are each independently a substituted or unsubstituted hydrocarbon group that may contain a heteroatom, n is a natural number of 1 to 3, m is a natural number of 0 to 2, o is a natural number of 0 to 1, and n + m + o = 3.). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Double role of the hydroxy group of phosphoryl in palladium(II)-catalyzed ortho -olefination: A combined experimental and theoretical investigation

Density functional theory calculations have been carried out on Pd-catalyzed phosphoryl-directed ortho-olefination to probe the origin of the significant reactivity difference between methyl hydrogen benzylphosphonates and dimethyl benzylphosphonates. The overall catalytic cycle is found to include four basic steps: C-H bond activation, transmetalation, reductive elimination, and recycling of catalyst, each of which is constituted from different steps. Our calculations reveal that the hydroxy group of phosphoryl plays a crucial role almost in all steps, which can not only stabilize the intermediates and transition states by intramolecular hydrogen bonds but also act as a proton donor so that the η1-CH3COO- ligand could be protonated to form a neutral acetic acid for easy removal. These findings explain why only the methyl hydrogen benzylphosphonates and methyl hydrogen phenylphosphates were found to be suitable reaction partners. Our mechanistic findings are further supported by theoretical prediction of Pd-catalyzed ortho-olefination using methyl hydrogen phenylphosphonate, which is verified by experimental observations that the desired product was formed in a moderate yield.

PHOSPHOTHIOPHENE AND PHOSPHOTHIAZOLE HCV POLYMERASE INHIBITORS

Provided herein are phosphothiophene and phosphothiazole compounds, for example, of any of Formulae I, IA, HA, IIIA, IVA, VA, VIA, VIIA, IB, HB, IIIB, IVB, VB, VIB and VIIB disclosed herein, pharmaceutical compositions comprising the compounds, and proces

Resolution of chiral phosphate, phosphonate, and phosphinate esters by an enantioselective enzyme library

An array of 16 enantiomeric pairs of chiral phosphate, phosphonate, and phosphinate esters was used to establish the breadth of the stereoselective discrimination inherent within the bacterial phosphotriesterase and 15 mutant enzymes. For each substrate,

Enantiopure O-substituted phenylphosphonothioic acids: Chiral recognition ability during salt crystallization and chiral recognition mechanism

The chiral recognition ability of enantiopure O-methyl, O-ethyl, O-propyl, and O-phenyl phenylphosphonothioic acids (1a-d) for various kinds of racemic amines during salt crystallization and the chiral recognition mechanism were thoroughly investigated. T

(1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphon...

A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described.The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by 31P NMR analysis.This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.

TETRAZOLE CATALYZED SYNTHESIS OF PHOSPHONATE ESTERS

1H-tetrazole selectively catalyzed mono addition of alcohols to phosphonic dichlorides such that mixed phosphonate diesters could be synthesized in high yields and under mild conditions.