4-Fluoro-3-nitrobenzoic acid

CAS Number 453-71-4

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers

4-Fluoro-3-nitrobenzoic acid CAS 453-71-4

A fluorinated building block with multiple functional groups

A versatile building block to synthesize benzimidazoles, benzoselenazoles and polymersomes for APIs and fluorescent dyes

Overview
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4-Fluoro-3-nitrobenzoic acid (CAS number 453-71-4) is derived from benzoic acid having a nitro and a fluoro substituents at 3- and 4-positions. The functional groups in 4-fluoro-3-nitrobenzoic acid possess different reactivities. The carboxylic acid reacts with alcohols for esters. Fluoride substituent favours nucleophilic aromatic substitution while nitro group can be reduced to an amine as a nucleophile. The ortho-position of fluoride and nitro makes 4-fluoro-3-nitrobenzoic acid an ideal precursor for making benzimidazoles derivatives. Benzimidazoles are active pharmaceutical ingredients applied as antimicrobials, opioids, antipsychotics and antihistamines. Benzoselenazoles (similar to benzimidazole, one nitrogen is replaced by a selenium atom) can be synthesized from 4-fluoro-3-nitrobenzoic acid reacting with isoselenocyanate.

It is feasible to attach various polymers to 4-fluoro-3-nitrobenzoic acid for block-co-polymers, in order to construct polymersomes.

Multiple functional groups

For facile synthesis

Fluorinated benzoic acid building block

For drug discovery, fluorescent dyes, and organic synthesis

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	453-71-4
Chemical Formula	C₇H₄FNO₄
Full Name	4-Fluoro-3-nitrobenzoic acid
Molecular Weight	185.11 g/mol
Synonyms	N/A
Classification / Family	Fluorinated building block, APIs, Fluorescent dyes

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 123 – 126 °C
Appearance	White to off-white powder

MSDS Documentation

4-Fluoro-3-nitrobenzoic acid MSDS Sheet

Literature and Reviews

Antituberculosis: synthesis and antimycobacterial activity of novel benzimidazole derivatives, Y. Yoon et al., Biomed Res. Int., 2013, 926309(2013); DOI: 10.1155/2013/926309.
Discovery of a potent and highly fluorescent sirtuin inhibitor, Y. Yoon et al., Med. Chem. Commun., 6, 1857–1863(2015); DOI: 10.1039/C5MD00307E.
Leuko-polymersomes, D. Hammer et al., Faraday Discuss., 139, 129-141(2008); DOI: 10.1039/B717821B.
Novel 1,2,5,-trisubstituted benzimidazoles potentiate apoptosis by mitochondrial dysfunction in panel of cancer cells, J. Swathantraiah et al., ACS Omega, 7, 46955−46971(2022); DOI: 10.1021/acsomega.2c06057.
MCC/SNAr methodology. part 2: novel three-step solution phase access to libraries of benzodiazepines, P. Tempest et al., Tetrahedron Lett., 44, 1947–1950(2013); DOI: 10.1016/S0040-4039(03)00084-4.
Regioselective synthesis of angular isocoumarinselenazoles: a benzoselenazole-directed, site-specific, ruthenium-catalyzed C(sp²)-H activation, S. Dhole et al., Adv. Synth. Catal., 360, 1–10(2018); DOI: 10.1002/adsc.201701256.

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