1663-55-4

Usage

Uses

Used in Pharmaceutical Industry:
Diethoxyphosphoryl-phenyl-methanol is used as an intermediate in the synthesis of diethyl hydroxy (substituted phenyl) methylphosphonates, which possess antioxidant activities. These synthesized compounds can be utilized in the development of pharmaceuticals targeting various health conditions and diseases where oxidative stress plays a significant role.
Used in Chitosan-catalyzed Synthesis:
In the field of organic chemistry, diethoxyphosphoryl-phenyl-methanol is used as a key intermediate in chitosan-catalyzed reactions. The chitosan-catalyzed synthesis of diethyl hydroxy (substituted phenyl) methylphosphonates with antioxidant properties is facilitated by this intermediate, leading to the production of compounds with potential applications in various industries, including pharmaceuticals and materials science.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 3591, 1953 DOI: 10.1021/ja01110a508

InChI:InChI=1/C11H17O4P/c1-3-14-16(13,15-4-2)11(12)10-8-6-5-7-9-10/h5-9,11-12H,3-4H2,1-2H3

Upstream product

• 100-52-7 benzaldehyde 
• 762-04-9 phosphonic acid diethyl ester 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 62968-01-8 Acetic acid (diethoxy-phosphoryl)-methylsulfanyl-methyl ester 
• 80255-46-5 diethyl 2,2,2-trichloroethoxycarbonylphosphonate 
• 71572-20-8 α-(diethoxyphosphinyl)benzyl diethyl phosphite 
• 76-05-1 trifluoroacetic acid 
• 3277-27-8 diethyl benzoylphosphonate 
• 109-73-9 N-butylamine 
• 227471-06-9 endo-6-formyl-exo-6-chlorobicyclo<3.1.0>hex-2-ene 
• 122-52-1 triethyl phosphite 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 762-04-9 Diethyl phosphonate 

Downstream Products

• 16153-59-6 (diethoxyphosphoryl)(phenyl)methyl acetate 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 1127-41-9 (α-hydroxybenzyl)phosphonic acid 
• 20369-41-9 diethyl fluoro-(phenyl)-methyl-phosphonate 
• 123959-75-1 α-(diethoxyphosphinyl)benzyl allophanate 
• 71572-20-8 α-(diethoxyphosphinyl)benzyl diethyl phosphite 
• 56152-41-1 N,N,N',N'-Tetraaethyl-P-(α-hydroxybenzyl)-phosphonyl-diamid 
• 27272-15-7 O-Aethyl-N,N-diaethyl-P-<α-hydroxy-benzyl>-phosphonoamidat 
• 53378-80-6 α-chlorobenzylphosphonic acid diethyl ester 
• 23755-78-4 diethyl (bromo(phenyl)methyl)phosphonate 
• 92074-50-5 ethyl α-chlorobenzylphosphonochloridate 
• 51761-45-6 Methanesulfonic acid (diethoxy-phosphoryl)-phenyl-methyl ester 
• 2530-54-3 O,O,O,O-tetraethylbenzylidenediphosphonate 
• 22730-58-1 diethyl (2,2-dicyano-1-(5-methylfuran-2-yl)ethyl)phosphonate 

Relevant academic research and scientific papers

First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases

Chiral phosphine oxides (Lewis bases) catalyze silicon tetrachloride-mediated, enantioselective phosphonylation of aldehydes with trialkyl phosphites (Abramov-type reaction), which leads to optically active α-hydroxyphosphonates with moderate enantioselec

Stereoselective Aldol Reactions via Enolates of α-Acylphosphonate Diesters

In the reaction between the lithium enolate (2) of diethyl propionylphosphonate (1) and benzaldehyde, the syn-product (3s) is formed with high diastereoselectivity, as a result of structural rigidity caused by Li+ interactions with the phosphoryl oxygen.

1,1,2-Triphenyl-1,2-ethanediol: A host for carboxylic acids and amides in coordinatoclathrates

The chiral diols (R)- and (S)-1 are found to form inclusion compounds with carboxylic acids and amides, as indicated by the relevant IR spectra. Two clathrates, (R)-1 · CH3CO2H and (S)-1 · CH3NHCHO have been characterized

Crystal structure, vibrational, spectral investigation, quantum chemical DFT calculations and thermal behavior of Diethyl [hydroxy (phenyl) methyl] phosphonate

Single Diethyl [hydroxy (phenyl) methyl] phosphonate (DHPMP) crystal with chemical formula C11H17O4P, was synthesized via the base-catalyzed Pudovik reaction and Lewis acid as catalyst. The results of SXRD analyzes indicate that this compound crystallizes into a mono-clinic system with space group P21/n symmetry and Z = 4. The crystal structure parameters are a = 9.293 ?, b = 8.103 ?, c = 17.542 ?, β = 95.329° and V = 1315.2 ?3, the structure displays one inter-molecular O—H?O hydrogen bonding. The UV–Visible absorption spectrum shows that the crystal exhibits a good optical transmission in the visible domain, and strong absorption in middle ultraviolet one. The vibrational frequencies of various functional groups present in DHPMP crystal have been deduced from FT-IR and FT-Raman spectra and then compared with theoretical values performed with DFT (B3LYP) method using 6-31G (p, d) basis sets. Chemical and thermodynamic parameters such as: ionization potential (I), electron affinity (A), hardness (σ), softness (η), electronegativity (χ) and electrophilicity index (ω), are also calculated using the same theoretical method. The thermal decomposition behavior of DHPMP, studied by using thermogravimetric analysis (TDG), shows a thermal stability until to 125 °C.

A study on the Kabachnik-Fields reaction of benzaldehyde, propylamine, and diethyl phosphite by in situ Fourier transform IR spectroscopy

The phospha-Mannich condensation of benzaldehyde, n-propylamine, and diethyl phosphite carried out at 80°C in acetonitrile takes place via the imine (PhC=N-Pr) intermediate as suggested by in situ FT-IR spectroscopy. Copyright

Tetrafluorine-containing ketones and acetoacetates: Synthesis and mechanistic study

Addition of trimethylsilyl trifluoroacetate to the carbanions of α-fluorobenzyl-phosphonate (3) or diisopropyl(fluorocarbethoxymethyl) phosphonate (9) formed the corresponding intermediates [CF3C(O)CFPh] -Li+ (10) and [CF3C(O)CFCO2Et] -Li+ (11), respectively. Subsequent protonation, alkylation or allylation of 10 and 11 afforded trifluoromethyl fluorobenzyl ketones 12 and ethyl 2,4,4,4-tetra-fluoroacetoacetates 13. Based on the results obtained, a plausible mechanism was proposed.

Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods

A series of ether phosphonates have been prepared by trichloroacetimidate and acetate coupling methods. Trichloroacetimidates or acetates were treated with primary and secondary alcohols as O-nucleophiles in the presence of catalytic TMSOTf to afford 21 examples of diethyl alkyloxy(substitutedphenyl)methyl phosphonates via C-O bond formation in 55-90% yields and short reaction time.

An efficient and simple strategy toward the synthesis of highly functionalized compounds

The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.

Synthesis of novel α-hydroxyphosphonates along with α-aminophosphonates as intermediates

New phosphoryl α-hydroxyphosphonates, their acylated derivatives, as well as α-aminophosphonates were synthesized as potentionally biologycally active substrates. The reverzible formation of α-hydroxyphosphonates allowing a few interesting side-reactions was also observed.

Method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis

The invention relates to a method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis. The method comprises the following steps: dissolving diethyl phosphite and aromatic aldehyde in an organic solvent, adding a cop