64611-67-2

Basic information

• Product Name: 2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE
• Synonyms: 2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE;2-Hydroxy-1-(4-nitrophenyl)ethanone;2-Hydroxy-4'-nitroacetophenone;2-hydroxy-1-(4-nitrophenyl)ethan-1-one;Ethanone, 2-hydroxy-1-(4-nitrophenyl)-
• CAS NO: 64611-67-2
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• Mol File: 64611-67-2.mol

Chemical Properties

• Melting Point: 140-143°C
• Boiling Point: 338.4°C at 760 mmHg
• Flash Point: 152.6°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 3.84E-05mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.42±0.10(Predicted)
• CAS DataBase Reference: 2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE(64611-67-2)
• EPA Substance Registry System: 2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE(64611-67-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 64611-67-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows for the development of new therapeutic agents with potential applications in treating a wide range of medical conditions.
Used in Dye Production:
In the dye industry, 2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE is utilized as a starting material for the production of various dyes. Its chemical properties enable the creation of dyes with specific color characteristics and stability, making it a valuable component in the formulation of different dye products.
Used in Chemical Manufacturing:
2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE plays a crucial role in the manufacturing of various chemicals, including pesticides and insecticides. Its versatile chemical properties allow for the development of effective and targeted pest control solutions, contributing to agricultural productivity and crop protection.
Used in Medicinal Applications:
2-HYDROXY-1-(4-NITROPHENYL)-1-ETHANONE is used as a potential medicinal agent due to its reported analgesic and anti-inflammatory properties. Its ability to alleviate pain and reduce inflammation makes it a promising candidate for the development of new medications to treat various conditions, such as arthritis, muscle pain, and other inflammatory disorders.

InChI:InChI=1/C8H7NO4/c10-5-8(11)6-1-3-7(4-2-6)9(12)13/h1-4,10H,5H2

Upstream product

• 99-81-0 4-Nitrophenacyl bromide 
• 4203-31-0 2-diazo-1-(4-nitrophenyl)ethanone 
• 132531-91-0 2-(4-nitrophenyl)-1-(phenylsulfenyl)-1,2-bis(trifluoroacetoxy)ethane 
• 100-19-6 (4-nitrophenyl)ethanone 
• 110944-98-4 2-iodo-1-(4-nitrophenyl)ethanone 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 6388-74-5 p-Nitrophenyloxirane 
• 77977-75-4 p-nitrophenylethylene glycol 
• 132531-70-5 (+/-)_S-2-(4-nitrophenyl)-1-(phenylsulfinyl)ethene 
• 78812-73-4 C₁₀H₁₃NO₅ 
• 34006-49-0 2-chloro-1-(4-nitrophenyl)ethanone 
• 124-41-4 sodium methylate 
• 100-13-0 4-nitrostyrene 

Downstream Products

• 62-23-7 4-nitro-benzoic acid 
• 77977-74-3 (S)-(+)-1-(4-nitrophenyl)-1,2-ethanediol 
• 56177-37-8 1-(4-nitrophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 357952-87-5 (S)-(+)-1-(4-Nitrophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 502934-29-4 (R)-1-(4-nitrophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 287944-34-7 (S)-(+)-1-(4-aminophenyl)-1,2-ethanediol 
• 287944-27-8 (S)-(+)-N-(4-(1,2-dihydroxyethyl)phenyl)methanesulfonamide 
• 606099-85-8 2-amino-4-(4-nitrophenyl)furan-3-carbonitrile 
• 33102-81-7 2-methyl-4-(4-nitrophenyl)thiazole 
• 2521-25-7 4-(4-nitrophenyl)-2-phenylthiazole 
• 1226790-03-9 C₉H₅Br₂NO₃ 
• 1244056-14-1 4-(4-nitrophenyl)-5H-[1,2,3]oxathiazole 2,2-dioxide 
• 5541-64-0 2-(4-nitro-phenyl)-quinoxaline 
• 14786-27-7 benzyl 4-nitrobenzoate 

Relevant articles and documents

Palladium-Catalyzed Diastereoselective Formal [5 + 3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring

A Pd-catalyzed formal [5 + 3] intermolecular cycloaddition reaction of isatin-derived α-(trifluoromethyl)imines with aryl substituted vinylethylene carbonates (VECs) has been reported, affording trifluoromethyl-group-containing spirooxindoles fused with an eight-membered ring as a single diastereoisomer in good yields in the presence of a Br?nsted acid in a one-pot manner under mild conditions. The asymmetric version of this reaction has been also realized using a chiral phosphine ligand along with the further transformation of the obtained product to give a spirooxindolo pyrrolidine derivative upon oxidation.

Spiro[indene-1,4′-oxa-zolidinones] Synthesis via Rh(III)-Catalyzed Coupling of 4-Phenyl-1,3-oxazol-2(3 H)-ones with Alkynes: A Redox-Neutral Approach

Transition-metal-catalyzed C-H activation synthesis of heterocyclic spiro[4,4]nonanes has persistently witnessed the use of additional stoichiometric transition-metal oxidant when employing C=C bond as the spiro ring closure site. Herein, we have addressed the issue by reporting a redox-neutral strategy for spiro[indene-1,4′-oxa-zolidinones] synthesis via Rh(III)-catalyzed coupling of 4-phenyl-1,3-oxazol-2(3H)-ones with alkynes. The synthesis features a broad substrate scope and high regiospecificity.

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.

Investigation and Application of Amphoteric α-Amino Aldehyde: An in Situ Generated Species Based on Heyns Rearrangement

In situ generation of the reactive amphoteric α-amino aldehyde with simple α-hydroxy ketones and phenylamine via Heyns rearrangement was proven to be feasible. Metal-free domino reactions based on this reactive intermediate were effectively used to afford important N-heterocycles including polysubstituted pyrroles, indoles, and quinoxalines conveniently. A simple starting material, water as the only byproduct, and diversity of the useful products will make this method greatly attractive for pharmaceutics.

Selective Debromination and α-Hydroxylation of α-Bromo Ketones Using Hantzsch Esters as Photoreductants

Two transformations initiated by photoinduced one-electron transfer to α-bromo ketones have been demonstrated. Hantzsch esters donate one electron to α-bromo ketones under photoirradiation, promoting reductive debromination. Subsequent reactions of the resulting radical species of the ketones with molecular oxygen and Hantzsch esters lead to α-hydroxylation or debromination, respectively. The relative dominance of the two pathways depends profoundly on the reaction conditions, including solvent, O2 levels, and the concentration of the Hantzsch esters. The synthetic protocols feature advantages because they require the environmentally benign sources, molecular oxygen and visible light.

Direct synthesis of α-hydroxyacetophenones through molecular iodine activation of carbon-carbon double bonds

An I2-promoted activation of carbon-carbon double bonds has been demonstrated. This simple and efficient domino process was utilized for the direct construction of α-hydroxyacetophenones in moderate to good yields from easily available styrenes at room temperature. This approach involved molecular iodine activation of carbon-carbon double bonds to form an iodonium intermediate. Moreover, TBHP was used as the sole effective oxidant and water was used as nucleophilic reagent in this reaction. This journal is

Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process

A very simple methodology was developed to transform racemic 1-(4-substitutedphenyl)-1,2-ethanediols using resting cells of Candida albicans CCT 0776 through a one-pot two-step process in which the (R)-stereoisomer was completely oxidized to the corresponding substituted-α-hydroxyacetophenones, which were completely reduced to produce (S)-1-(4-substitutedphenyl)-1,2-ethanediols in good isolated yield (60-85%) and with high enantiomeric excess (99% ee). The overall process corresponded to an enantioselective deracemization by stereoinversion of the (R)-enantiomer. The process was not achieved for other similar 1,2-diols using the same reaction conditions, which indicates a structural restriction of substrates by the active pocket of the enzymes of C. albicans involved in the stereoinversion process.

Oxidative coupling of terminal alkyne with α-hydroxy ketone: An expedient approach toward ynediones

An efficient and mild copper-catalyzed one-pot approach toward ynediones has been established. A variety of ynediones were constructed directly through oxidative coupling of alkyne with α-hydroxy ketone. Oxygen-oxidizing and neutral conditions in one-pot for a wide range of substrates including natural product derivatives make this transformation highly efficient and practical. On the basis of control experiments, in situ IR measurements, and isotopic labeling experiments, a plausible mechanism involving intermediate phenylglyoxal was drawn. Applications by synthesis of various heterocycles were also investigated.

Experimental study on the reaction pathway of α-haloacetophenones with NaOMe: Examination of bifurcation mechanism

The reaction of PhCOCH2Br and NaOMe in MeOH gave PhCOCH 2OH as the major product and PhCOCH2OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by direct substitution. Substituent effects on the reaction rates, as well as the effects of NaOMe concentration on the rate and product ratio for both reactions of PhCOCH2Br and PhCOCH2CI are in line with the mechanism that the alcohol and ether products were formed via two independent and concurrent routes, carbonyl addition and a-carbon attack, respectively, and thus the reaction mechanism could be different from the bifurcation mechanism previously predicted for the reaction of PhCOCH2Br by a simulation study in the gas phase.

Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity.