46417-99-6

Basic information

• Product Name: 2-nitro-1-(4-nitrophenyl)ethanone
• CAS NO: 46417-99-6
• Molecular Formula: C₈H₆N₂O₅
• Molecular Weight: 210.1436
• Mol File: 46417-99-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 388.7°C at 760 mmHg
• Flash Point: 202.9°C
• Density: 1.443g/cm³
• Vapor Pressure: 3.01E-06mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 2-nitro-1-(4-nitrophenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitro-1-(4-nitrophenyl)ethanone(46417-99-6)
• EPA Substance Registry System: 2-nitro-1-(4-nitrophenyl)ethanone(46417-99-6)

Safety Data

• Hazardous Substances Data: 46417-99-6(Hazardous Substances Data)

Upstream product

• 7647-01-0 hydrogenchloride 
• 555-16-8 4-nitrobenzaldehdye 
• 99-81-0 4-Nitrophenacyl bromide 
• 62-23-7 4-nitro-benzoic acid 
• 18731-47-0 1-(4-nitrophenyl)-2-nitroethanol 
• 75-52-5 nitromethane 
• 10364-96-2 N-(4-nitrobenzoyl)imidazole 
• 4231-71-4 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone 
• 955558-85-7 4-nitro-3-(4-nitro-phenyl)-5-phenyl-isoxazole 
• 7559-38-8 1-(2-bromo-2-nitrovinyl)-4-nitrobenzene 
• 509-14-8 tetranitromethane 
• 74812-79-6 1-(4-nitrophenyl)-1-trimethylsilyloxyethylene 
• 3156-41-0 1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene 

Downstream Products

• 75-52-5 nitromethane 
• 62-23-7 4-nitro-benzoic acid 
• 563-70-2 bromonitromethane 
• 619-50-1 4-nitrobenzoic acid methyl ester 

Relevant articles and documents

Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions

We have developed a practical, general protocol for denitration of readily available α-nitroketones with sulfur and amines to access a broad range of α-ketothioamides under mild conditions. Such a reaction proceeds under metal-, oxidant-, and catalyst-free conditions to provide synthetically useful α-ketothioamides. Furthermore, the mild reaction conditions tolerate a wide range of substrates especially for the synthesis of aliphatic α-ketothioamides which are rarely reported.

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.

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.