6881-61-4

Usage

Uses

Used in Water Treatment Industry:
Phosphonic acid, benzoylis used as a chelating agent for effectively sequestering metal ions, such as calcium and magnesium, in water treatment processes. This application helps prevent the precipitation of these ions, ensuring the efficient functioning of water systems.
Used in Cooling Water Systems:
In the industry of cooling water systems, phosphonic acid, benzoylis utilized as a corrosion inhibitor. Its ability to form protective films on metal surfaces helps prevent corrosion, thereby extending the life of equipment and reducing maintenance costs.
Used in Boiler Water Treatment:
Phosphonic acid, benzoylis employed as a scale inhibitor in boiler water treatment. By preventing the formation of scale, which can lead to reduced heat transfer efficiency and potential equipment damage, this chemical compound contributes to the optimal performance and safety of boilers.
Used in Pharmaceutical Synthesis:
As a chemical intermediate, phosphonic acid, benzoylplays a crucial role in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the development of new drugs and the improvement of existing ones, contributing to advancements in the field of medicine.

Upstream product

• 3277-27-8 diethyl benzoylphosphonate 
• 18106-71-3 dimethyl benzoylphosphonate 
• 33876-85-6 benzoylphosphonic acid di(trimethylsilyl) ester 
• 98-88-4 benzoyl chloride 
• 119859-55-1 (E)-α-hydroxyiminobenzylphosphonic acid 

Downstream Products

• 145298-95-9 benzoylphosphonic dichloride 
• 145298-96-0 P,P'-dibenzoylpyrophosphonic dichloride 
• 65-85-0 benzoic acid 
• 89849-82-1 triethylammonium 5'-O-(dimethoxytrityl)thymidine 3'-benzoylphosphonate 
• 22950-57-8 diisopropyl benzoylphosphonate 
• 145298-97-1 2-propyl hydrogen benzoylphosphonate 
• 89849-87-6 C₅₀H₅₁N₄O₁₅P 
• 89849-90-1 5'-O-dimethoxytritylthymidin-3'-yl 3'-O-(1,3-benzodithiol-2-yl)thymidin-5'-yl benzoylphosphonate 
• 3278-14-6 N-phenethylbenzamide 
• 49615-28-3 ethyl 3-benzamidopropanoate 

Relevant academic research and scientific papers

Mechanism-based inactivation of benzoylformate decarboxylase, a thiamin diphosphate-dependent enzyme

Benzoylformate decarboxylase (BFD) from Pseudomonas putida is a thiamin diphosphate-dependent enzyme that catalyzes the non-oxidative decarboxylation of benzoylformate. Here we report the discovery of a mechanism-based inhibitor of BFD that is unusual in

Chemoselective N-acylation via condensations of N-(benzoyloxy)amines and α-ketophosphonic acids under aqueous conditions

(Chemical Equation Presented) A new amide-forming reaction with N-benzoyloxyamines and α-ketophosphonic acids was investigated. A mixed solvent of t-BuOH/water (1:1) at 40°C provided the desired amide in high yield (71-96%). Both phosphonic acids (9, 12, or 13) and their disodium salts (e.g., 10) were shown to react with the respective N-benzoyloxyamines (1b and 4) in excellent yields. The phosphonic acid methyl ester monosodium salt 11 did not react under these conditions. However, compound 11 did provide the desired amide in 22% yield upon addition of 2 equiv of TFA. The N-acylation reaction is highly chemoselective for N-benzoyloxyamines as both aliphatic amines and N-hydroxylamines were shown not to react productively with the α-ketophosphonic acids under the conditions tested. Moreover, the α-ketophosphonic acids are more selective than the related α-ketocarboxylic acid systems, which react with both the N-hydroxylamines and N-benzoyloxyamines. In this regard, this novel phosphonic acid methodology provides a new high-yielding, chemoselective acylating reagent for further study.

A kinetic study of competing fragmentation and hydrolyses of phenyl hydrogen α-hydroxyiminobenzylphosphonate - A case of acid mediated inhibition of acid catalysis

The behavior of phenyl hydrogen α-hydroxyiminobenzylphosphonate (E)-2 in aqueous hydrochloric acid solution was examined by 31P NMR spectroscopy and by HPLC. Compound (E)-2 was found to undergo two competing acid-catalyzed reactions. 1) Fragmentation to phenyl phosphate (6) and benzonitrile, similar to the fragmentation of other hydroxyiminophosphonates to metaphosphate examined previously. The fragmentation of (E)-2 was found to be slower by a factor of 4 than that of hydrogen methyl α-hydroxyiminobenzylphosphonate ((E)-1). This phenomenon is interpreted in terms of inductive effects on the suggested metaphosphate intermediate. 2) Compound (E)-2 was found to undergo hydrolytic cleavage of the oxime group giving NH2OH and hydrogen phenyl benzoylphosphonate (4), which was found to hydrolyze to phenol and benzoylphosphonic acid (5). The latter reacted with the NH2OH liberated in the previous step to give α-hydroxyiminobenzylphosphonic acid ((E)-3), which fragmented to benzonitrile and phosphoric acid. The rate of a possible hydrolysis of the phenol group in oxime (E)-2 was shown to be slower by two orders of magnitude than that from ketone 4. This phenomenon is interpreted in terms of acid mediated retardation of acid catalyzed hydrolysis of phenol due to initial protonation of the oxime nitrogen in (E)-2.

THE REACTION OF BENZOYLPHOSPHONIC ACID WITH THIONYL CHLORIDE. THE FORMATION OF BENZOYLPHOSPHONIC DICHLORIDE AND P,P'-DIBENZOYLPYROPHOSPHONIC DICHLORIDE

The reaction of benzoylphosphonic acid (3) with thionyl chloride leads to the formation of benzoylphosphonic dichloride (5) and P,P'-dibenzoylpyrophosphonic dichloride (6).These products were identified by (31)P nmr spectra and through their products of a

Acylphosphonic acids and methyl hydrogen acylphosphonates: Physical and chemical properties and theoretical calculations

Acylphosphonic acids (5) and methyl hydrogen acylphosphonates (3) were synthesized by di- and mono-demethylation of dimethyl acylphosphonates (1). Spectroscopic data (i.r., 31P and 1H n.m.r.) are reported for these types of compounds for the first time. Examination of their hydrolytic stability under acidic and basic conditions revealed that except for methyl hydrogen acylphosphonates (3) that are unstable under highly alkaline pH conditions, the C-P bond in these types of compounds is stable in most cases. Nucleophilic reagents, e.g. amines, borohydride, or hydroxylamine react with the carbonyl group of ionized acylphosphonates with the preservation of the C-P bond, to yield α-imino-, α-hydroxy-, or α-oxyimino- alkylphosphononate anions, respectively. Semi-empirical quantum mechanical (MNDO/H) calculations were performed on benzoylphosphonic acid (5c) and on the esters and anions derived from it, as representatives of their classes, in order to assess bond lengths and preferred conformations, and to estimate charges on the carbonyl and phosphoryl groups. Calculations show that for both neutral and ionized (anions) compounds free rotation around the C-P bond is expected due to the low energy barriers.

Acylphosphonates. 4. Synthesis of Dithymidine Phosphonate: A New Method for Generation of Phosphonate Function via Aroylphosphonate Intermediates

Dithymidine phosphonate (10) was synthesized by a new method via dithymidine aroylphosphonates (3) in which the aroyl group served as a protecting group for O=P-H functions.In a way analogous to the phosphotriester method, 3 was prepared by successive con

The Dealkylation of Phosphate and Phosphonate Esters by Iodotrimethylsilane: A Mild and Selective Procedure

Iodotrimethylsilane transforms alkyl esters of phosphorus oxyacids into their corresponding trimethylsilyl esters and alkyl iodide.The reaction is rapid and quantitative at room temperature.The reagent has no effect on aryl phosphate ester functions or upon alkyl carboxylate, ether, bromoalkane, vinyl, and ethynyl functions under the conditions employed for transesterification.The trimethylsilyl esters can be isolated by distillation or solvolysed without purification using methanol or water to afford dealkylated phosphate and phosphonate species.Selective monodealkylation of dialkyl phosphonates cannot be achieved using only one equivalent of the reagent, wich leads to the formation of mixed products.