4-Fluoro-β-nitrostyrene

CAS Number 706-08-1

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers, Non-Heterocyclic Building Blocks

A fluorinated nitrostyrene building block

Used as a Michael acceptor in conjugated addition for chromenes/benzopyran for APIs

Overview
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4-Fluoro-β-nitrostyrene (CAS number 706-08-1) is a fluorinated styrene with a nitro group substituted on the β-carbon. 4-Fluoro-β-nitrostyrene is a typical Michael acceptor with the electron withdrawing nitro group, which is readily for conjugated addition. When the conjugated addition is catalysed by a chiral ligand, such as l-proline, syn-addition is favoured, and the chirality of the Michael adducts can be selectively controlled. Hence, 4-fluoro-β-nitrostyrene has been exploited for chiral γ-nitroaldehydes, a precursor for pharmaceutically active γ-aminobutyric acid (GABA). 4-Fluoro-β-nitrostyrene is also used to synthesise benzopyran(chromenes) derivatives as pharmaceutical active ingredients(APIs).

In antibacterial activity study, 4-fluoro-β-nitrostyrene binds to PTP1B enzymes via hydrogen bonding interaction. It is followed by a Michael addition of thiol groups leading to the inhibition of protein tyrosine phosphatases in the microorganisms.

Multiple functional groups

For facile synthesis

Fluorinated nitrostyrene building block

For organic synthesis, medicinal chemistry and biochemistry research

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	706-08-1
Chemical Formula	C₈H₆FNO₂
Full Name	1-Fluoro-4-(2-nitroethenyl)benzene
Molecular Weight	167.14 g/mol
Synonyms	1-(4-Fluorophenyl)-2-nitroethene, 1-Fluoro-4-(2-nitroethenyl)benzene, 1-(4-Fluorophenyl)-2-nitroethylene
Classification / Family	Fluorinated building blocks, Michael acceptors, APIs, Heterocycles, Antibiotics

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 99 °C – 102 °C
Appearance	Cream powder

MSDS Documentation

4-Fluoro-β-nitrostyrene MSDS Sheet

Literature and Reviews

Augmentation of enantioselectivity by spatial aminocatalyst: synthesis of 2-alkyl/aryl-3-nitro-2H-chromenes by tandem oxa-Michael-Henry reaction, R. Mohanta et al., J. Org. Chem., 85(7), 4627–4636(2020);DOI: 10.1021/acs.joc.9b03366.
N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts, V. Poláčková et al., Beilstein J. Org. Chem., 17, 2629–2641(2021); DOI: 10.3762/bjoc.17.176.
Comparisons of halogenated β-nitrostyrenes as antimicrobial agent, H. Cornell et al., Appl. Sci., 4, 380–389(2014); DOI: 10.3390/app4030380.
Highly efficient Michael-type addition of acetaldehyde to β-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase, T. Narancic et al., Bioresour. Technol., 142, 462–468(2013); DOI: 10.1016/j.biortech.2013.05.074.
Using mutability landscapes of a promiscuous tautomerase to guide the engineering of enantioselective Michaelases, J.-Y. van der Meer et al., Nat. Commun., 7, 10911(2016); DOI: 10.1038/ncomms10911.
Diastereo- and enantioselective syntheses of trisubstituted benzopyrans by Cascade reactions catalyzed by monomeric and polymeric recoverable bifunctional thioureas and squaramides, J. Andrés et al., ACS Omega, 3, 16591–16600(2018); DOI: 10.1021/acsomega.8b02302.

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