609339-99-3

Basic information

• Product Name: α-hydroxy-p-nitrobenzyl carbanion
• Synonyms: α-hydroxy-p-nitrobenzyl carbanion
• CAS NO: 609339-99-3
• Molecular Weight: 152.13
• Mol File: 609339-99-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: α-hydroxy-p-nitrobenzyl carbanion(CAS DataBase Reference)
• NIST Chemistry Reference: α-hydroxy-p-nitrobenzyl carbanion(609339-99-3)
• EPA Substance Registry System: α-hydroxy-p-nitrobenzyl carbanion(609339-99-3)

Safety Data

• Hazardous Substances Data: 609339-99-3(Hazardous Substances Data)

Upstream product

• 77977-75-4 p-nitrophenylethylene glycol 
• 609339-95-9 tert-butyl hydroxy-(4-nitrophenyl)acetate 
• 75288-21-0 2-bromo-2-(4-nitrophenyl)acetyl chloride 
• 29704-35-6 tert-butyl 2-acetoxy-2-(4-nitrophenyl)acetate 
• 29898-08-6 2-acetoxy-2-(4-nitrophenyl)acetic acid 
• 4578-72-7 2-bromo-2-(4-nitrophenyl)acetic acid 
• 10098-39-2 2-hydroxy-2-(4-nitrophenyl)acetic acid 

Downstream Products

• 555-16-8 4-nitrobenzaldehyde anion radical 

Relevant articles and documents

Chemistry of photogenerated α-hydroxy-p-nitrobenzyl carbanions in aqueous solution: Protonation vs. disproportionation

The photochemistry of p-nitrobenzyl derivatives 6-10 has been studied in aqueous solution as a function of pH, using product analysis, UV-vis spectrophotometry, and laser flash photolysis (LFP). The compounds were chosen with the aim of further exploring the propensity of these systems to give rise to α-hydroxy-p-nitrobenzyl carbanions on photolysis, and to study their mechanisms of subsequent reaction, α-Hydroxy-substituted carbanions are anions that cannot be readily formed using thermal routes but which are believed to have some interesting chemistry. Three methods were employed for photogenerating these carbanions: (i) decarboxylation; (ii) retro-Aldol reaction; and (iii) carbon acid deprotonation. All three methods proved to be successful using the p-nitrobenzyl chromophore. Photogenerated α-hydroxy-p-nitrobenzyl carbanions react via disproportionation, giving rise to oxidized and reduced products; simple protonation of the anion was undetectable.