5275-69-4

Basic information

• Product Name: 2-ACETYL-5-NITROFURAN
• Synonyms: 2-ACETYL-5-NITROFURAN;Methyl(5-nitrofuran-2-yl) ketone;1-(5-nitrofuran-2-yl)ethanone
• CAS NO: 5275-69-4
• Molecular Formula: C₆H₅NO₄
• Molecular Weight: 155.12
• Mol File: 5275-69-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 78.5 °C
• Boiling Point: 278.88°C (rough estimate)
• Flash Point: 90.2°C
• Appearance: /
• Density: 1.5553 (rough estimate)
• Vapor Pressure: 0.086mmHg at 25°C
• Refractive Index: 1.5423 (estimate)
• CAS DataBase Reference: 2-ACETYL-5-NITROFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYL-5-NITROFURAN(5275-69-4)
• EPA Substance Registry System: 2-ACETYL-5-NITROFURAN(5275-69-4)

Safety Data

• Hazardous Substances Data: 5275-69-4(Hazardous Substances Data)

Usage

General Description

2-Acetyl-5-nitrofuran is a synthetic chemical compound with the molecular formula C6H6N2O4. It is a nitrofuran derivative and is used as an antimicrobial agent and food preservative. It is commonly used in the preservation of meat, poultry, and fish. The compound exhibits antibacterial and antifungal properties, making it effective in preventing food spoilage caused by microbial contamination. However, 2-acetyl-5-nitrofuran has raised concerns about its potential carcinogenicity and toxic effects on humans, leading to its prohibition in several countries, including the European Union. Overall, the chemical is used primarily in food preservation but is subject to regulatory restrictions due to its potential health risks.

InChI:InChI=1/C6H5NO4/c1-4(8)5-2-3-6(11-5)7(9)10/h2-3H,1H3

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 108-24-7 acetic anhydride 
• 1107580-77-7 (5-acetylfuran-2-yl)boronic acid 
• 7697-37-2 nitric acid 
• 25084-14-4 5-nitrofuran-2-carboxylic chloride 
• 105-53-3 diethyl malonate 
• 186581-53-3 diazomethane 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 18753-50-9 1-(5-nitrofuran-2-yl)ethan-1-ol 

Downstream Products

• 83132-58-5 (6-Chloro-2-{[1-(5-nitro-furan-2-yl)-eth-(E)-ylidene]-hydrazono}-benzothiazol-3-yl)-acetic acid ethyl ester 
• 90251-70-0 (E)-3-(4-Chloro-phenyl)-1-(5-nitro-furan-2-yl)-propenone 
• 77604-98-9 (E)-3-(4-Bromo-phenyl)-1-(5-nitro-furan-2-yl)-propenone 
• 14549-95-2 1-(5-nitro-furan-2-yl)-5-phenyl-penta-2,4-dien-1-one 
• 77604-94-5 1-(5-nitro-2-furyl)-3-(2-nitrophenyl)-2-propen-1-one 
• 61619-68-9 3-(5-nitro-furan-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 531-82-8 2-acetylamino-4-(5-nitro-2-furyl)thiazole 
• 51948-48-2 [5-morpholin-4-ylmethyl-4-(5-nitro-furan-2-yl)-thiazol-2-yl]-phenyl-amine 
• 90251-71-1 2,3-dibromo-1-(5-nitro-2-furyl)-3-(2-nitrophenyl)propan-1-one 
• 90251-76-6 2,3-Dibromo-3-(2-chloro-phenyl)-1-(5-nitro-furan-2-yl)-propan-1-one 
• 90251-75-5 2,3-Dibromo-3-(4-bromo-phenyl)-1-(5-nitro-furan-2-yl)-propan-1-one 
• 90251-77-7 2,3-dibromo-1-(5-nitro-2-furyl)-3-(p-chlorophenyl)-propan-1-one 
• 90251-81-3 (Z)-2-Bromo-3-(4-chloro-phenyl)-1-(5-nitro-furan-2-yl)-propenone 

Relevant articles and documents

ROTATIONAL ISOMERS OF THE RADICAL-ANIONS OF 2-CARBONYL-CONTAINING DERIVATIVES OF 5-NITROFURAN

The radical-anions of 2-carbonyl-containing derivatives of 5-nitrofuran were obtained by electrochemical generation.Their ESR spectra indicate the existence of a mixture of O,O-cis and O,O-trans rotational isomers.The parameters of the isomers were identified by INDO calculations.The more polar form (the cis isomer) is more stable in polar media.

NITRATION

The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.

Bioreductively activatable prodrug conjugates of phenstatin designed to target tumor hypoxia

A variety of solid tumor cancers contain significant regions of hypoxia, which provide unique challenges for targeting by potent anticancer agents. Bioreductively activatable prodrug conjugates (BAPCs) represent a promising strategy for therapeutic intervention. BAPCs are designed to be biologically inert until they come into contact with low oxygen tension, at which point reductase enzyme mediated cleavage releases the parent anticancer agent in a tumor-specific manner. Phenstatin is a potent inhibitor of tubulin polymerization, mimicking the chemical structure and biological activity of the natural product combretastatin A-4. Synthetic approaches have been established for nitrobenzyl, nitroimidazole, nitrofuranyl, and nitrothienyl prodrugs of phenstatin incorporating nor-methyl, mono-methyl, and gem-dimethyl variants of the attached nitro compounds. A series of BAPCs based on phenstatin have been prepared by chemical synthesis and evaluated against the tubulin-microtubule protein system. In a preliminary study using anaerobic conditions, the gem-dimethyl nitrothiophene and gem-dimethyl nitrofuran analogues were shown to undergo efficient enzymatic cleavage in the presence of NADPH cytochrome P450 oxidoreductase. Each of the eleven BAPCs evaluated in this study demonstrated significantly reduced inhibitory activity against tubulin in comparison to the parent anti-cancer agent phenstatin (IC50?=?1.0?μM). In fact, the majority of the BAPCs (seven of the eleven analogues) were not inhibitors of tubulin polymerization (IC50?>?20?μM), which represents an anticipated (and desirable) attribute for these prodrugs, since they are intended to be biologically inactive prior to enzyme-mediated cleavage to release phenstatin.

Novel functionalized melamine-based nitroheterocycles: Synthesis and activity against trypanosomatid parasites

Human African trypanosomiasis (HAT), caused by the protozoan parasite Trypanosoma brucei spp., is a major health problem in sub-Saharan Africa. New drugs are urgently required for the disease. Selective uptake of toxic compounds into trypanosomes has been achieved by exploiting plasma membrane transporters. For example, the P2 aminopurine transporter, along with other transporters, selectively concentrates melamine and benzamidine moieties into trypanosomes. We have previously reported the use of the melamine motif to selectively target nitrofuran to the trypanosome. In this paper we report the further investigation of the structure activity relationships and the effect of the introduction of different functionalized substituents onto the melamine unit. Most of the compounds tested in vitro for their trypanocidal activity showed activities in the submicromolar range against T. b. rhodesiense. The Royal Society of Chemistry 2009.