69646-14-6

Usage

Uses

Used in Flame Retardant Industry:
DIETHYL(2-HYDROXYPHENYL)PHOSPHONATE is used as a flame retardant for various industrial and consumer products to enhance their fire resistance and safety.
Used in Plasticizer Industry:
This organophosphate compound is used as a plasticizer to increase the flexibility and workability of certain materials.
Used in Pharmaceutical and Agrochemical Synthesis:
DIETHYL(2-HYDROXYPHENYL)PHOSPHONATE is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
However, it is important to note that due to its potential hazards, proper handling, storage, and disposal of DIETHYL(2-HYDROXYPHENYL)PHOSPHONATE are necessary to minimize its environmental and health risks.

InChI:InChI=1/C10H15O4P/c1-3-13-15(12,14-4-2)10-8-6-5-7-9(10)11/h5-8,11H,3-4H2,1-2H3

Upstream product

• 16462-86-5 2-(chlorophenyl) diethylphosphate 
• 2510-86-3 O,O-diethyl O-phenyl phosphate 
• 108-95-2 phenol 
• 598-02-7 Diethyl phosphate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 533-58-4 2-Iodophenol 
• 762-04-9 phosphonic acid diethyl ester 
• 824-91-9 O-methoxymethylphenol 
• 16462-84-3 diethyl(2-iodophenyl)phosphate 
• 124551-12-8 2-(methoxymethoxy)phenylphosphonic acid diethyl ester 
• 16462-85-4 2-bromophenyl diethyl phosphate 

Downstream Products

• 91633-07-7 Diethyl 2-(diethoxyphosphinyl)phenyl phosphate 
• 268741-89-5 (2-hydroxy-5-iodo-phenyl)-phosphonic acid diethyl ester 
• 1335044-31-9 C₁₄H₁₄F₉O₆PS 
• 53839-05-7 o-anisylphosphonic dichloride 
• 125727-35-7 sodium o-diethoxyphosphinylphenolate 
• 53104-46-4 2-hydroxybenzenephosphonic acid 
• 69646-17-9 o-hydroxyphenylphosphine 
• 135979-79-2 (2-hydroxyphenyl)dipentylphosphine oxide 
• 135979-81-6 2-(Dioctyl-phosphinoyl)-phenol 
• 129529-22-2 2-(Dipropyl-phosphinoyl)-phenol 
• 60253-98-7 o-Hydroxyphenyl-diaethylphosphinoxid 
• 135979-80-5 2-(Dihexyl-phosphinoyl)-phenol 
• 135979-78-1 2-(Diisobutyl-phosphinoyl)-phenol 
• 124629-83-0 o-dibutylphosphinoylphenol 

Relevant academic research and scientific papers

Enantioselective and Regioselective Hydroetherification of Alkynes by Gold-Catalyzed Desymmetrization of Prochiral Phenols with P-Stereogenic Centers

The gold(I)-catalyzed enantioselective hydroetherification of alkynes was achieved via desymmetrization of prochiral bisphenols bearing P-stereogenic centers. (S)-DTBM-Segphos(AuCl)2/AgNTf2 proved to be a highly efficient catalyst system for this transformation, affording P-chiral cyclic phosphine oxides in good yields with high enantioselectivities (with up to 99% ee). The same catalyst system allowed for the enantioselective desymmetrization of dialkynes. Synthetic transformations of the cyclization products afforded other P-chiral molecules with high enantiospecificity.

Phosphoryl Analogs of Salicylic Acid: Synthesis and Analgesic and Anti-Inflammatory Activity

The synthetically convenient method of preparation of unexplored phosphoryl analogs of salicylic acid (2-hydroxyphenylphosphonic and 2-hydroxyphenylphosphinic acids) has been developed for the search of novel nonsteroidal anti-inflammatory drugs. It has been shown that 2-hydroxyphenylphosphinic acid is a lowtoxic compound (LD50 3500 mg/kg) exhibiting analgesic activity significantly higher than both 2-hydroxyphenylphosphonic acid and the reference compound (sodium metamizole).

Insertion of Arynes into P-O Bonds: One-Step Simultaneous Construction of C-P and C-O Bonds

The insertion of arynes into P-O bonds for the preparation of o-hydroxy-substituted arylphosphine oxides, -phosphinates, and -phosphonates is described. This novel reaction leads to the simultaneous formation of C-P and C-O bonds in one step with good yie

Stereoselective synthesis of phosphoryl-substituted phenols

Copper-catalyzed C-X activation-phosphorylation of aryls bearing different groups has been achieved using P(O)-H compounds as efficient phosphorylation reagents without the assistance of any ligand. Optically active H-phosphinates can also act as good substrates in the reaction, giving the (Sp)-phosphoryl substituted phenolic compounds stereospecifically with retention of configuration at the phosphorus center. Furthermore, it is shown that the migration of phosphorus on O-aryl phosphonates from oxygen to carbon also proceeds stereospecifically to produce the corresponding optically active (Rp)-phosphoryl-substituted phenolic compounds with retention of configuration at phosphorus via treatment with lithium diisopropylamide (LDA). Plausible mechanisms have been proposed for these reactions.

Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase

Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC50 values of 4.8?μM, 2.3?μM and 1.9?μM, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors.

Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: Discovery of new effective chiral ligands

(Chemical Equation Presented) The hemilabile ligand Me-DuPHOS(O) 2 has proven to be a successful ligand for the copper-catalyzed addition of diethylzinc to N-phosphinoylimines. The corresponding α-chiral amines were obtained in high yields (80-98%) and enantiomeric ratios (19.0:1 to 99.0:1 er). Furthermore, this Cu?2 catalytic system has been shown to be effective in the addition of diethylzinc to nitroalkenes and in the reduction of β,β-disubstituted vinyl phenyl sulfones. This paper describes a general structure/selectivity study in which the three ligand subunits (chiral phospholane-linker-labile coordinating group (Z)) are systematically modified and tested in the copper-catalyzed addition of diethylzinc to the N-phosphinoylimine 1 derived from benzaldehyde. This study led to the discovery of a new class of effective chiral ligands that combine a chiral phospholane unit and an achiral phosphine oxide.

A novel phosphotyrosine mimetic 4′-carboxymethyloxy-3′-phosphonophenylalanine (Cpp): Exploitation in the design of nonpeptide inhibitors of pp60Src SH2 domain

The novel phosphotyrosine (pTyr) mimetic 4′-carboxymethyloxy-3′-phosphonophenylalanine (Cpp) has been designed and incorporated into a series of nonpeptide inhibitors of the SH2 domain of pp60c-Src (Src) tyrosine kinase. A 2.2 A X-ray crystal structure of 1a bound to a mutant form of Lck SH2 domain provides insight regarding the structure-activity relationships and supports the design concept of this new pTyr mimetic.

SYNTHESIS AND SUBSTITUENT EFFECT ON 31P NMR CHEMICAL SHIFT OF ORTHO-HYDROXYARYL DIALKYL PHOSPHINE OXIDES

In this paper, the synthetic methods for the preparation of o-hydroxyaryl dialkyl phosphine oxides (1) are introduced.The title compounds with low bulky substituent are synthesized successfully by the reactions of Grignard reagents with diethyl o-hydroxya

Steric and electronic effects in the aryl phosphate to arylphosphonate rearrangement

A number of carboxy substituted aryl phosphates have been prepared and subjected to anionic rearrangement conditions to provide the corresponding phenolic phosphonates. Steric effects of the phosphate ester group and the electronic effects of the aryl car