367-80-6

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-fluoro-3-nitrobenzoate is used as a building block for the synthesis of various drugs and pharmaceutical products, leveraging its unique chemical structure to contribute to the development of novel therapeutic agents.
Used in Organic Synthesis:
Ethyl 4-fluoro-3-nitrobenzoate is utilized as an intermediate in organic synthesis, where its chemical and biological properties are explored and harnessed for the creation of new compounds with potential applications in various fields.
Used in Research:
Ethyl 4-fluoro-3-nitrobenzoate serves as a starting material in research, where its properties are studied to develop new chemical compounds and understand its potential applications in different industries.

InChI:InChI=1/C9H8FNO4/c1-2-15-9(12)6-3-4-7(10)8(5-6)11(13)14/h3-5H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 400-94-2 4-fluoro-3-nitrobenzoyl chloride 
• 16588-16-2 ethyl 4-chloro-3-nitrobenzoate 
• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 64-67-5 diethyl sulfate 
• 109-63-7 boron trifluoride diethyl etherate 

Downstream Products

• 455-75-4 ethyl 3-amino-4-fluorobenzoate 
• 917237-08-2 4-(2-methoxycarbonyl-phenylsulfanyl)-3-nitro-benzoic acid ethyl ester 
• 885312-79-8 ethyl 4-(cycloheptylamino)-3-nitrobenzoate 
• 87815-77-8 4-cyclohexylamino-3-nitrobenzoic acid ethyl ester 
• 913532-36-2 4-(3-hydroxymethyl-phenylamino)-3-nitro-benzoic acid ethyl ester 
• 935433-67-3 4-(2-methoxycarbonyl-phenoxy)-3-nitrobenzoic acid ethyl ester 
• 935433-78-6 4-tert-butylsulfanyl-3-nitrobenzoic acid ethyl ester 
• 935433-71-9 4-(4-fluoro-2-ethoxycarbonylphenylsulfanyl)-3-nitrobenzoic acid ethyl ester 
• 935873-06-6 ethyl 4-(3-methyl-3-nitro-butylamino)-3-nitro-benzoate 
• 1012071-58-7 C₁₁H₁₄FNO₂ 
• 1042663-51-3 ethyl 3-benzylamino-4-fluorobenzoate 
• 71254-72-3 ethyl 3-nitro-4-piperidin-1-ylbenzoate 
• 71254-73-4 4-morpholin-4-yl-3-nitro-benzoic acid ethyl ester 
• 71302-98-2 ethyl 4-(azepan-1-yl)-3-nitrobenzoate 

Relevant academic research and scientific papers

Novel fluorescent benzimidazoles: Synthesis, characterization, crystal structure and evaluation of their anticancer properties

Background: The benzimidazole core structure is an interesting platform for drug discovery since it possess a wide spectrum of pharmacological activities such as antiviral, anti-inflammatory and anticancer. Previously the antiproliferative effect of novel

Structure-Activity Relationships and Computational Investigations into the Development of Potent and Balanced Dual-Acting Butyrylcholinesterase Inhibitors and Human Cannabinoid Receptor 2 Ligands with Pro-Cognitive in Vivo Profiles

The enzyme butyrylcholinesterase (BChE) and the human cannabinoid receptor 2 (hCB2R) represent promising targets for pharmacotherapy in the later stages of Alzheimer's disease. We merged pharmacophores for both targets into small benzimidazole-based molecules, investigated SARs, and identified several dual-acting ligands with a balanced affinity/inhibitory activity and an excellent selectivity over both hCB1R and hAChE. A homology model for the hCB2R was developed based on the hCB1R crystal structure and used for molecular dynamics studies to investigate binding modes. In vitro studies proved hCB2R agonism. Unwanted μ-opioid receptor affinity could be designed out. One well-balanced dual-acting and selective hBChE inhibitor/hCB2R agonist showed superior in vivo activity over the lead CB2 agonist with regards to cognition improvement. The data shows the possibility to combine a small molecule with selective and balanced GPCR-activity/enzyme inhibition and in vivo activity for the therapy of AD and may help to rationalize the development of other dual-acting ligands.

Synthesis and Crystal Structures of Ethyl 2-(4-Methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate Dihydrate and Its Building Block 4-Fluoro-3-nitrobenzoic Acid

The title compound, ethyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate (5), was synthesized and its crystal structure was studied by single-crystal X-ray diffraction technique. Compound 5 is crystallized in the centrosymmetric triclinic space group P1 ˉ with Z = 4 and Z′ = 2, and unit-cell parameters of a = 8.9190 (3) ?, b = 12.6888 (4) ?, c = 14.7111 (5) ?, α = 98.4855 (10)°, β = 101.6379 (9)°, γ = 95.4346 (10)° and V = 1599.43 (9) ?3. Its starting material, 4-fluoro-3-nitrobenzoic acid (1), is crystallized in the non-centrosymmetric monoclinic space group P21 and Z = 4 with unit-cell parameters of a = 3.7170 (4) ?, b = 12.6475 (13) ?, c = 15.5237 (15) ?, α = 90°, β = 91.9786 (16)°, γ = 90° and V = 729.35 (13) ?3. It was noted that strong hydrogen bonds play important roles in the crystal packing of both compounds, especially in 5, in which the co-crystallized water molecules act as both strong hydrogen bond donor and strong hydrogen bond acceptor. Graphical Abstract: Two molecule of compound 5 crystallized in a non symmetrical manner with four co-crystallized water molecules which play an important role in the crystal packing as strong hydrogen-bond donors. [Figure not available: see fulltext.].

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

The alkylation of carboxylic acids by an ethyl moiety of boron trifluoride etherate in the absence of ethyl alcohol from the reaction system is unexpected and novel. Both aromatic and aliphatic carboxylic acids were clearly alkylated affording good yields in short reaction times with the exception of nicotinic acid that necessitated an overnight reaction. It was noted that while ortho-substituted hydroxyl groups of carboxylic acids investigated were not affected by alkylation, those of meta- and para-substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function.

Antituberculosis agents bearing the 1,2-disubstituted benzimidazole scaffold

Abstract: The emergence of drug-resistant strains in recent years has fueled the epidemic of tuberculosis. This necessitates the development of new chemical scaffolds to curb resistant tuberculosis for effective control of this disease. In this study, we have designed and synthesized two series of benzimidazole derivatives. Their antimycobacterial activities were initially evaluated using Mycobacterium tuberculosis H37RV strains. The most potent analog (6h) was further assessed using various drug-resistant M. tuberculosis strains. This report described the importance of benzimidazoles as new antitmycobacterial agents targeting both the M. tuberculosis H37RV as well as the drug-resistant-tuberculosis strains. The trifluoromethyl group which was essential for antimycobacterial activity was also highlighted. Graphical Abstract: Two series of benzimidazole derivatives and their antimycobacterial activities were evaluated using M. tuberculosis H37RV (MTB-H37RV) strains. Compound 6h was identified as the most potent among all synthesized compounds. The most potent analog was further assessed using various drug-resistant MTB strains. In addition, the trifluoromethyl was identified as an important substitution in giving good antimycobacterial effect. [InlineMediaObject not available: see fulltext.]

COMPOUND AND METHOD FOR INHIBITING SIRTUIN ACTIVITIES

A compound of formula wherein R1 is selected from the group consisting of hydrogen, halogen, hydroxyl, carboxyl, alkyl of up to 5 carbon atoms, imidazolyl, piperazinyl, morpholinyl, benzyl, R4OH or R4COOH, where R4 is (CH2)m and m is an integer of from 1 to 4; R2 is selected from the group consisting of hydrogen, phenyl or 3-(2-oxopyrrolidin-l-yl) propyl; and R3 is hydrogen or alkyl of from 1-4 carbon atoms.

ANTI-ANGIOGENIC AGENTS AND USES THEREOF

There is herein disclosed a compound of formula I: or a salt solvate or pharmaceutically acceptable derivative thereof, wherein R1 to R7 is as defined herein for use in the treatment of angenogenis and related conditions.

Potent sirtuin inhibition with 1,2,5-trisubstituted benzimidazoles

Two series of compounds were synthesized based on the benzimidazole scaffold. The compounds were subsequently screened for their SIRT1, SIRT2 and SIRT3 activities. Three of the compounds showed good inhibitory activity against SIRT2 in this study with the most potent compound (5i) having an IC50 value of 2.9 μM. Molecular docking analysis demonstrated that 5i was able to inhibit SIRT2 by displacing the co-factor NAD+ in the active site. This was further confirmed experimentally by ligand-NAD+ competitive assay.

Structural Modifications of Benzimidazoles via Multi-Step Synthesis and Their Impact on Sirtuin-Inhibitory Activity

Benzimidazole derivatives have been shown to possess sirtuin-inhibitory activity. In the continuous search for potent sirtuin inhibitors, systematic changes on the terminal benzene ring were performed on previously identified benzimidazole-based sirtuin i

Synthesis and evaluation of compounds containing 4-arylpiperazinyl moieties linked to a 2-(pyridin-3-yl)-1H-benzimidazole as p38 MAP kinase inhibitors

A series of novel ethyl 1-(2-(4-(2-amino-5-(ethoxycarbonyl) phenyl) piperazin-1-yl) ethyl)-2-(2-(substituted) pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxylate analogues were synthesized and screened as p38 MAP kinase inhibitors. The 4-chlorophenoxy substi