28519-13-3

Basic information

• Product Name: Phosphoric acid, bis(1-methylethyl) phenylmethyl ester
• CAS NO: 28519-13-3
• Molecular Formula: C13H21O4P
• Molecular Weight: 272.281
• Mol File: 28519-13-3.mol

Chemical Properties

• CAS DataBase Reference: Phosphoric acid, bis(1-methylethyl) phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid, bis(1-methylethyl) phenylmethyl ester(28519-13-3)
• EPA Substance Registry System: Phosphoric acid, bis(1-methylethyl) phenylmethyl ester(28519-13-3)

Safety Data

• Hazardous Substances Data: 28519-13-3(Hazardous Substances Data)

Upstream product

• 1611-31-0 diisopropylphosphate 
• 17683-09-9 benzyl-(p-methylphenyl)triazene 
• 80354-12-7 diisopropyl phosphorobromidate 
• 100-51-6 benzyl alcohol 
• 55-91-4 diisopropyl phosphofluoridate 

Relevant articles and documents

Distribution and fate of diethyl malonate and diisopropyl fluorophosphate on pig skin in vitro

The in vitro distribution and fate of [14C]diethyl malonate and [14C]diisopropyl fluorophosphate were evaluated on normal and heat-treated pig skin. The extent of hydrolysis from the skin surface, skin, and receptor fluid was determined. A significant skin-mediated hydrolysis (15-35% of applied dose) was observed for diethyl malonate in normal skin, but not in heat-treated skin. These results indicated that a heat labile process (e.g., enzymatic hydrolysis) was in part responsible for the degradation of diethyl malonate after topical application to normal skin. Heat treatment tripled the skin penetration of diisopropyl fluorophosphate and reduced the amount of recovered hydrolysis product, diisopropyl phosphoric acid. Enzymatic and spontaneous hydrolysis, as well as impurity, accounted for the presence of degradation product.

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