46270-50-2

Basic information

• Product Name: 1-(2-methoxyphenyl)-2-nitroethanone
• CAS NO: 46270-50-2
• Molecular Formula: C₉H₉NO₄
• Molecular Weight: 195.1721
• Mol File: 46270-50-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 336.3°C at 760 mmHg
• Flash Point: 162.6°C
• Density: 1.237g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 1-(2-methoxyphenyl)-2-nitroethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-methoxyphenyl)-2-nitroethanone(46270-50-2)
• EPA Substance Registry System: 1-(2-methoxyphenyl)-2-nitroethanone(46270-50-2)

Safety Data

• Hazardous Substances Data: 46270-50-2(Hazardous Substances Data)

Usage

Chemical class

Nitro compounds

Physical state

Yellow crystalline solid

Common use

Intermediate in organic synthesis

Applications

Preparation of pharmaceuticals, agrochemicals, dyes, and flavoring agents

Biological activities

Studied for anti-inflammatory and anti-cancer properties

Industrial and research applications

Wide range due to chemical structure and properties

Upstream product

• 3316-24-3 1-methoxy-2-((E)-2-nitrovinyl)benzene 
• 75-52-5 nitromethane 
• 135-02-4 ortho-anisaldehyde 
• 306990-93-2 (1H-benzo[d][1,2,3]triazol-1-yl)(2-methoxyphenyl)methanone 
• 38316-04-0 1-(2-methoxy-phenyl)-2-nitro-ethanol 
• 529-28-2 4-iodoanisol 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 579-75-9 2-Methoxybenzoic acid 
• 861084-23-3 2-(1,2-dibromo-2-nitro-ethyl)-anisole 
• 15241-32-4 1-methoxy-2-(2-nitrovinyl)benzene 
• 860741-58-8 1-(2-methoxy-phenyl)-2-nitro-ethanone-dimethylacetal 

Downstream Products

• 610758-06-0 (R)-1-(2-methoxyphenyl)-2-nitroethan-1-ol 
• 1395341-67-9 2-methyl-5-(o-methoxyphenyl)oxazole 
• 81589-32-4 N-<(4-Methylphenyl)sulfonyl>-2-methoxybenzenecarboxamide 
• 38316-04-0 1-(2-methoxy-phenyl)-2-nitro-ethanol 
• 579-75-9 2-Methoxybenzoic acid 
• 1313263-62-5 (R,Z)-1-isopropoxy-5-nitro-1-oxo-4-phenylpent-2-en-2-yl 2-methoxybenzoate 
• 1313263-47-6 (R,Z)-4-(4-chlorophenyl)-1-methoxy-5-nitro-1-oxopent-2-en-2-yl 2-methoxybenzoate 
• 1313263-58-9 (R,Z)-1-ethoxy-5-nitro-1-oxo-4-phenylpent-2-en-2-yl 2-methoxybenzoate 
• 1313263-34-1 (R,Z)-1-methoxy-5-nitro-1-oxo-4-phenylpent-2-en-2-yl 2-methoxybenzoate 
• 1313263-66-9 (S,Z)-4-cyclohexyl-1-ethoxy-5-nitro-1-oxopent-2-en-2-yl 2-methoxybenzoate 
• 1313263-52-3 (R,Z)-4-(2-fluorophenyl)-1-methoxy-5-nitro-1-oxopent-2-en-2-yl 2-methoxybenzoate 
• 1313263-43-2 (R,Z)-1-methoxy-4-(4-methoxyphenyl)-5-nitro-1-oxopent-2-en-2-yl 2-methoxybenzoate 
• 1313263-41-0 (R,Z)-1-methoxy-5-nitro-1-oxo-4-p-tolylpent-2-en-2-yl 2-methoxybenzoate 
• 1313263-64-7 (S,Z)-1-ethoxy-5-methyl-4-(nitromethyl)-1-oxohex-2-en-2-yl 2-methoxybenzoate 

Relevant articles and documents

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones

We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.

Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α-Nitroketones and in situ-Generated ortho-Quinone Methides: Route to 2-(1-Arylethyl)phenols

An organocatalytic asymmetric domino Michael/acyl transfer reaction between α-nitroketones and o-quinone methides is disclosed. o-Quinone methides are generated in situ from 2-sulfonylmethylphenols in basic medium. With 10 mol% of bifunctional squaramide catalyst, high yields and excellent enantioselectivities are achieved for a variety of O-acyl 2-(1-arylethyl)phenols under mild reaction condition. (Figure presented.).

Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone

A catalyst free protocol has been developed for nucleophilic Csp2-Csp3 bond cleavage of α-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted α-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively.