169172-42-3

Basic information

• Product Name: Ethyl hydrogen hydroxyphenylmethylphosphonate
• Synonyms: Ethyl hydrogen hydroxyphenylmethylphosphonate
• CAS NO: 169172-42-3
• Molecular Weight: 216.174
• Mol File: 169172-42-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Ethyl hydrogen hydroxyphenylmethylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl hydrogen hydroxyphenylmethylphosphonate(169172-42-3)
• EPA Substance Registry System: Ethyl hydrogen hydroxyphenylmethylphosphonate(169172-42-3)

Safety Data

• Hazardous Substances Data: 169172-42-3(Hazardous Substances Data)

Upstream product

• 1498-42-6 phosphorodichloridous acid ethyl ester 
• 100-52-7 benzaldehyde 
• 1663-55-4 diethyl [hydroxy(phenyl)methyl]phosphonate 
• 76-05-1 trifluoroacetic acid 
• 13716-45-5 diethyl trimethylsilyl phosphite 
• 39059-59-1 ethyl bis(trimethylsilyl) phosphite 

Downstream Products

• 64-17-5 ethanol 
• 1127-41-9 (α-hydroxybenzyl)phosphonic acid 

Relevant articles and documents

Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates

The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The fission of the second P-O-C bond was found to be the rate-determining step.

Enantioselective Deprotonation of Benzyl Phosphates by Homochiral Lithium Amide Bases - Configurational Stability of Benzyl Carbanions with a Dialkoxyphosphoryloxy Substituent and Their Rearrangement to Optically Active α-Hydroxy Phosphonates

Benzyl dialkyl phosphates are deprotonated enantioselectively by homochiral lithium amides of isopropyl(1-phenylethyl)amine or bis(1-phenylethyl)amine.The short-lived benzylic carbanions formed are virtually configurationally stable relative to the rearrangement to optically active phenylhydroxymethylphosphonates.The enantiomeric excesses are up to 50percent.The pro-(S) hydrogen is removed by amides having (S) configuration.Homochiral diethyl (S)-phenylmethyl phosphate is deprotonated by both LDA and n-BuLi with a high primary kinetic isotope effect (kH/D ca. 50) and isomerizes to the corresponding α-hydroxy phosphonate with an enantiomeric excess of up to 85percent. - Keywords: Phosphate-phosphonate rearrangement / Carbanions, benzylic, configurational stability of / Phosphonates / Lithium amides, homochiral