20782-91-6

Basic information

• Product Name: 4-(BROMOMETHYL)-3-NITROBENZOIC ACID
• Synonyms: 2-(BROMOETHYL)-5-NITROFURAN;2-(BROMOMETHYL)-5-NITROFURAN;4-(BROMOETHYL)-3-NITROBENZOIC ACID;4-CARBOXY-2-NITROBENZYLBROMID;TIMTEC-BB SBB003091;TIMTEC-BB SBB000452;2-(BROMOMETHYL)-5-NITROFURAN 97%;5-Nitro-2-furfuryl bromide, GC 97%
• CAS NO: 20782-91-6
• Molecular Formula: C₅H₄BrNO₃
• Molecular Weight: 206
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Furans;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 20782-91-6.mol

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 277.8°C at 760 mmHg
• Flash Point: 121.8°C
• Appearance: /
• Density: 1.813g/cm³
• Vapor Pressure: 0.00749mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 4-(BROMOMETHYL)-3-NITROBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(BROMOMETHYL)-3-NITROBENZOIC ACID(20782-91-6)
• EPA Substance Registry System: 4-(BROMOMETHYL)-3-NITROBENZOIC ACID(20782-91-6)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-43-36-22
• Safety Statements: 26-36/37/39-45-36/37
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 19
• Hazardous Substances Data: 20782-91-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-(Bromomethyl)-3-nitrobenzoic acid is used as a building block in organic synthesis for the creation of more complex molecules. Its unique functional groups allow for various chemical reactions, facilitating the synthesis of a wide range of organic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-(Bromomethyl)-3-nitrobenzoic acid is utilized as a key intermediate in the development of pharmaceuticals. Its structural features enable the design and synthesis of novel drug candidates with potential therapeutic applications.
Used in Antimicrobial Agents:
4-(Bromomethyl)-3-nitrobenzoic acid is known for its antimicrobial activity, making it a valuable component in the development of antimicrobial agents. It can be incorporated into pharmaceuticals and agrochemicals to combat microbial infections and improve public health.
Used in Dye Production:
Due to its aromatic properties, 4-(Bromomethyl)-3-nitrobenzoic acid has potential applications in the dye production industry. It can be used to synthesize dyes with specific color characteristics and properties, contributing to the development of new dye products.
Used in Material Science:
4-(Bromomethyl)-3-nitrobenzoic acid's functional groups and aromatic nature also make it a candidate for material science applications. It can be used in the development of new materials with unique properties, such as improved stability, reactivity, or other desirable characteristics.

InChI:InChI=1/C5H4BrNO3/c6-3-4-1-2-5(10-4)7(8)9/h1-2H,3H2

Upstream product

• 92-55-7 5-nitro-2-furfuraldehyde diacetate 
• 2493-04-1 (5-nitrofuran-2-yl)methanol 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 66628-32-8 5-nitro-2-furylnitromethane 

Downstream Products

• 53174-11-1 5-(5-nitro-furan-2-ylmethylsulfanyl)-3-phenyl-3H-[1,3,4]thiadiazole-2-thione 
• 88796-61-6 N-(5-nitrofurfuryl)-4-aminobenzoic Acid 
• 88796-62-7 N-(5-nitrofurfuryl)-2-aminobenzoic Acid 
• 88796-69-4 N,N'-Bis(5-Nitrofurfuryl)-4-aminobenzoic Acid 
• 61266-74-8 2-(4-chloro-phenylsulfanylmethyl)-5-nitro-furan 
• 40941-14-8 2-nitro-5-phenylsulfanylmethyl-furan 
• 119321-44-7 C₁₄H₁₄N₄O₄S*BrH 
• 119321-42-5 1-(4-nitrobenzylidene)-3-(5-nitro-2-furfuryl)thiosemicarbazonium bromide 
• 119321-40-3 1-benzylidene-3-(5-nitro-2-furfuryl)thiosemicarbazonium bromide 
• 119321-41-4 C₁₃H₁₁ClN₄O₃S*BrH 
• 134834-80-3 C₁₅H₁₄N₄O₃S*BrH 
• 119321-43-6 C₁₃H₁₁N₅O₅S*BrH 
• 40941-17-1 5-nitro-2-furfuryl phenyl sulphone 
• 116728-54-2 2-Benzylsulfanylmethyl-5-nitro-furan 

Relevant articles and documents

Synthesis, characterization and antiinflammatory activity of chalcone derivatives linked with apocynin and 5-nitrofuran moiety

The present paper describes the synthesis of some new chalcone derivatives i.e. 1-[3-methoxy-4-(5-nitro-furan-2-ylmethoxy)-phenyl]-3-(substituted phenyl)-propenone derivatives (9A-9K) from furfural and apocynin as starting materials. Claisen-Schmidt reaction of 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7) with aromatic aldehydes (8A-K) under solvent free conditions using solid NaOH as catalyst at room temperature resulted in the formation of chalcone derivatives (9A-9K) in 86-96 % yield. These compounds were characterized by 1H NMR, Mass and IR spectroscopy and were evaluated for their anti-inflammatory activity.

7-Piperazinylquinolones with methylene-bridged nitrofuran scaffold as new antibacterial agents

Quinolone class of antibacterial agents has considerable attention to find new useful antibacterial agents. Therefore, a series of N-substituted piperazinylquinolones bearing (5-nitrofuran-2-yl)methyl moiety were synthesized and evaluated against a variety of bacteria. The methylene-bridged nitrofuran functionality has been recently used in oxazolidinone class of antibacterial agents containing piperazinyl moiety by introducing ranbezolid as a 5-nitrofuran analog of eperzolid. The results of antibacterial evaluation revealed that the influence of (5-nitrofuran-2-yl) attachment to the 7-piperazinylquinolones against different bacterial species depends on the type of substituents at the N-1 and C-8 positions. Better results were obtained with ethyl at N-1 and CF at C-8 in the term of activity against Bacillus subtilis and E. coli. While, the optimum activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella pneumonia was entailed by a molecule possessing cyclopropyl at N-1 and CH at C-8.

Design, synthesis, biological screening and molecular docking studies of novel multifunctional 1,4-di (aryl/heteroaryl) substituted piperazine derivatives as potential antitubercular and antimicrobial agents

In this paper, two series of novel multifunctional 1, 4-di (aryl/heteroaryl) substituted piperazine derivatives (6a-d & 7a-d) were synthesized, characterized, and evaluated for their antitubercular, antibacterial, and antifungal activities. A step-wise reduction, bromination and substitution reactions on various aldehydes resulted in alcohols (2a–d), bromides (3a–d), and titled novel compounds (6a–d & 7a–d) in moderate to good yields (48–85%). The novel compounds were evaluated for their antitubercular and antimicrobial activities. Compound 7a exhibited promising antitubercular activity (MIC: 0.65 μg/mL) almost equal to the Rifampicin, while the rest of the compounds were moderately active against MTB H37Rv except 6b. Compounds 7a and 6b showed good activity against tested fungal pathogens. Compounds 7a and 7b were proven as the best bacterial agents. Molecular docking studies were in agreement with the in-vitro results. Docking analyses show that all the synthesized molecules bind to the target protein Mtb RNAP (PDB ID: 5UHC) fairly strongly. All the compounds were evaluated for their in vitro cytotoxicity effect using the MTT assay method against human cancer cell line MCF-7. The compounds demonstrated growth inhibitory effect on the cell line with significant IC50 values ranging between 8.20 and 34.45 μM. Most importantly, compound 7a displayed good binding affinity towards the tested protein with binding energy ?7.30 kcal/mol and a stronger hydrogen bond distance of 2.2 ? with ASN-493 residue. Thus, the present research highlighted the potential role of novel piperazine derivatives as potential antitubercular, and antimicrobial candidates and further good research into optimization might result in the development of new antitubercular drug candidates.

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

ANTIBACTERIAL THERAPEUTICS AND PROPHYLACTICS

The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.

Radical-Nucleophilic Substitution (SRN1) Reactions: Electron Spin Resonance Studies of Electron-capture Processes. Part 4.1 α-Substituted 2-Methyl-5-nitrofurans

We have probed two steps postulated for the radical-nucleophilic substitution (SRN1) mechanism for α-substituted 2-methyl-5-nitrofurans (O2NFurCH2X) by detecting the intermediates involved using e.s.r. spectroscopy.These two steps are the elect