188119-50-8

Basic information

• Product Name: diethyl (2-(4-hydroxyphenyl)-2-oxoethyl) phosphate
• Synonyms: diethyl (2-(4-hydroxyphenyl)-2-oxoethyl) phosphate
• CAS NO: 188119-50-8
• Molecular Weight: 288.237
• Mol File: 188119-50-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: diethyl (2-(4-hydroxyphenyl)-2-oxoethyl) phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (2-(4-hydroxyphenyl)-2-oxoethyl) phosphate(188119-50-8)
• EPA Substance Registry System: diethyl (2-(4-hydroxyphenyl)-2-oxoethyl) phosphate(188119-50-8)

Safety Data

• Hazardous Substances Data: 188119-50-8(Hazardous Substances Data)

Upstream product

• 99-93-4 4-Hydroxyacetophenone 
• 2345-34-8 4-acetyloxy-benzoic acid 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 598-02-7 Diethyl phosphate 
• 52727-19-2 4-(2-diazoacetyl)-3-methoxyphenyl acetate 
• 845504-48-5 4-(tert-butyldiphenylsilyloxy)-α-hydroxyacetophenone 
• 845504-47-4 2-(4-(tert-butyldiphenylsilyloxy)phenyl)-2-oxoethyl bromide 
• 845504-46-3 1-(4-((tertbutyldiphenylsilyl)oxy)phenyl)ethan-1-one 
• 845504-49-6 4-tert-butyldiphenylsilyloxyphenacyl diethyl phosphate 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 67353-83-7 tetrabutylammonim salt of diethylphosphoric acid 

Downstream Products

• 502-87-4 4-methylene-cyclohexa-2,5-dienone 
• 156-38-7 4-hydroxyphenylacetate 
• 16010-88-1 tert-butyl 2-(4-hydroxyphenyl)acetate 
• 99-93-4 4-Hydroxyacetophenone 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 

Relevant articles and documents

2-Diazo-1-(4-hydroxyphenyl)ethanone: A versatile photochemical and synthetic reagent

α-Diazo arylketones are well-known substrates for Wolff rearrangement to phenylacetic acids through a ketene intermediate by either thermal or photochemical activation. Likewise, α-substituted p-hydroxyphenacyl (pHP) esters are substrates for photo-Favorskii rearrangements to phenylacetic acids by a different pathway that purportedly involves a cyclopropanone intermediate. In this paper, we show that the photolysis of a series of α-diazo-p- hydroxyacetophenones and p-hydroxyphenacyl (pHP) α-esters both generate the identical rearranged phenylacetates as major products. Since α-diazo-p-hydroxyacetophenone (1a, pHP N2) contains all the necessary functionalities for either Wolff or Favorskii rearrangement, we were prompted to probe this intriguing mechanistic dichotomy under conditions favorable to the photo-Favorskii rearrangement, i.e., photolysis in hydroxylic media. An investigation of the mechanism for conversion of 1a to p-hydroxyphenyl acetic acid (4a) using time-resolved infrared (TRIR) spectroscopy clearly demonstrates the formation of a ketene intermediate that is subsequently trapped by solvent or nucleophiles. The photoreaction of 1a is quenched by oxygen and sensitized by triplet sensitizers and the quantum yields for 1a-c range from 0.19 to a robust 0.25. The lifetime of the triplet, determined by Stern-Volmer quenching, is 31 ns with a rate for appearance of 4a of k = 7.1 × 10 6 s-1 in aq. acetonitrile (1:1 v:v). These studies establish that the primary rearrangement pathway for 1a involves ketene formation in accordance with the photo-Wolff rearrangement. Furthermore we have also demonstrated the synthetic utility of 1a as an esterification and etherification reagent with a variety of substituted α-diazo-p- hydroxyacetophenones, using them as synthons for efficiently coupling it to acids and phenols to produce pHP protect substrates. The Royal Society of Chemistry and Owner Societies.

Ultrafast time-resolved study of photophysical processes involved in the photodeprotection of p-hydroxyphenacyl caged phototrigger compounds

A combined femtosecond Kerr gated time-resolved fluorescence (fs-KTRF) and picosecond Kerr gated time-resolved resonance Raman (ps-KTR3) study is reported for two p-hydroxyphenacyl (pHP) caged phototriggers, HPDP and HPA, in neat acetonitrile a