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Product Code B2551-5g
Price $113 ex. VAT

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A fluorinated nitrostyrene building block

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

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

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated nitrostyrene building block

For organic synthesis, medicinal chemistry and biochemistry research

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High purity 706-08-01

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

4-Fluoro-β-nitrostyrene chemical structure, CAS 706-08-1.
4-Fluoro-β-nitrostyrene chemical structure, CAS 706-08-1

Product Details

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

MSDS Documentation

4-Fluoro-β-nitrostyrene4-Fluoro-β-nitrostyrene MSDS Sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. Comparisons of halogenated β-nitrostyrenes as antimicrobial agent, H. Cornell et al., Appl. Sci., 4, 380–389(2014); DOI: 10.3390/app4030380.
  4. 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.
  5. 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.
  6. 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.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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