22391-01-1

Basic information

• Product Name: Benzenemethanol, a-methylene-4-nitro-, acetate (ester)
• CAS NO: 22391-01-1
• Molecular Formula: C10H9NO4
• Molecular Weight: 207.186
• Mol File: 22391-01-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-methylene-4-nitro-, acetate (ester)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-methylene-4-nitro-, acetate (ester)(22391-01-1)
• EPA Substance Registry System: Benzenemethanol, a-methylene-4-nitro-, acetate (ester)(22391-01-1)

Safety Data

• Hazardous Substances Data: 22391-01-1(Hazardous Substances Data)

Upstream product

• 591-87-7 Allyl acetate 
• 100-19-6 (4-nitrophenyl)ethanone 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 485842-62-4 (S)-1-(4-nitrophenyl)ethyl acetate 
• 19759-27-4 (1R)-1-(4-nitrophenyl)ethyl acetate 
• 19759-27-4 4-(α-acetoxyethyl)-1-nitrobenzene 
• 56858-46-9 1-(4-nitrophenyl)-2-(toluene-4-sulfonyl)ethanone 
• 721-68-6 3,3,3-trifluoro-1-(4-nitrophenyl)propan-1-one 
• 38488-17-4 1-(4-nitrophenyl)-2-(phenylsulfonyl)ethan-1-one 
• 82415-38-1 ethyl 1-hydroxy-2-oxo-1-cyclopentanecarboxylate 

Relevant articles and documents

Visible-Light-Promoted Synthesis of α-CF2H-Substituted Ketones by Radical Difluoromethylation of Enol Acetates

An efficient and novel visible-light-promoted radical difluoromethylation of enol acetates for the synthesis of α-CF2H-substituted ketones has been described. Upon irradiation under blue LED with catalytic amounts of fac-Ir(ppy)3, this photocatalytic procedure employs difluoromethyltriphenylphosphonium bromide as a radical precursor. Various α-CF2H-substituted ketones are successfully created via designed systems based on the SET process. The methodology has also provided an operationally simple process with broad functional group compatibility.

Synthesis of 1,4-Diketones from β-Oxo Esters and Enol Acetates by Cerium-Catalyzed Oxidative Umpolung Reaction

Cyclic β-oxo esters are converted with enol acetates in a cerium-catalyzed, oxidative Umpolung reaction to furnish 1,4-diketones with up to 95 % yield. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C-C coupling reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl3·7H2O as precatalyst.

Modular P-OP ligands in rhodium-mediated asymmetric hydrogenation: A comparative catalysis study

Highly efficient and enantioselective hydrogenation reactions for α-(acylamino)acrylates, itaconic acid derivatives and analogues, α-substituted enol ester derivatives, and α-arylenamides (25 substrates) catalyzed by chiral cationic rhodium complexes of a set of P-OP ligands have been developed. The catalytic systems derived from these P-OP ligands provided a straightforward access to enantiomerically enriched α-amino acid, carboxylic acid, amine, and alcohol derivatives that are valuable chiral building blocks. Excellent efficiencies (full conversion in all cases) and extremely high enantiomeric excesses (94-99% ee) were achieved for a wide range of α-substituted enol ester derivatives, regardless of the substitution pattern. The R-oxy group of the ligand (methoxy or triphenylmethoxy) strongly influences the enantioselectivity and catalytic activity. Greater steric bulk around the metal centre correlated to greater (or similar) enantioselectivity, but also to slower hydrogenation. Furthermore, the hydrogenation rates observed with the four model substrates follow the same trend, independently of the R-oxy group of the ligand: methyl 2-acetamidoacrylate>dimethyl itaconate>1-phenylvinyl acetate>N-(1- phenylvinyl)acetamide. A substrate-to-catalyst ratio (S/C) of up to 10,000:1 was sufficient for total hydrogenation of a model substrate of intermediate reactivity (dimethyl itaconate), and did not imply any loss in conversion or enantioselectivity. Copyright