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478717

Sigma-Aldrich

2-(2-Nitrovinyl)furan

98%

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About This Item

Empirical Formula (Hill Notation):
C6H5NO3
CAS Number:
699-18-3
Molecular Weight:
139.11
MDL number:
MFCD00030600
UNSPSC Code:
12352100
PubChem Substance ID:
24871569
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

72-75 °C (lit.)

SMILES string

[O-][N+](=O)\C=C\c1ccco1

InChI

1S/C6H5NO3/c8-7(9)4-3-6-2-1-5-10-6/h1-5H/b4-3+

InChI key

WVUICGOYGDHVBH-ONEGZZNKSA-N

General description

2-(2-Nitrovinyl)furan (NVF) is a 2-furylethylene derivative with a potential antiprotozoal property. It forms solid inclusion complexes with cyclodextrine (CD) derivatives, 2-hydroxypropyl-β-cyclodextrin and sulfobutyl ether-β-cyclodextrin. The Friedel-Crafts alkylation of naphthols with NVF in aqueous medium and catalyst-free condition has been reported. The formation of Morita-Baylis-Hillman (MBH) adduct via MBH reaction of NVF with diisopropyl azodicarboxylate (DIAD) has been studied.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

478717-5G:
478717-BULK:
478717-1KG:
478717-VAR:
478717-1G:

Certificates of Analysis (COA)

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Highly efficient hydrazination of conjugated nitroalkenes via imidazole or DMAP mediated Morita-Baylis-Hillman reaction.
Dadwal M, et al.
Organic & Biomolecular Chemistry, 4(13), 2525-2528 (2006)
Catalyst-free Friedel-Crafts alkylation of naphthols with nitrostyrenes in the presence of water.
Halimehjani AZ, et al.
Tetrahedron Letters, 50(13), 1441-1443 (2009)
T O Ajiboye et al.
Microbial pathogenesis, 91, 107-114 (2015-12-02)
The involvement of reactive oxygen species and oxidative stress in 2-(2-nitrovinyl) furan mediated bacterial cell death was investigated in Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. Time kill assay resulted in significant decrease in the optical density and colony-forming unit
Diana Oliveira et al.
International journal of molecular sciences, 22(2) (2021-01-14)
Quorum sensing (QS) plays an essential role in the production of virulence factors, in biofilm formation and antimicrobial resistance. Consequently, inhibiting QS is being considered a promising target for antipathogenic/anti-virulence therapies. This study aims to screen 2-nitrovinylfuran derivatives structurally related
Characterization and molecular modeling of the inclusion complexes of 2-(2-nitrovinyl) furan (G-0) with cyclodextrines.
Ruz V, et al.
International Journal of Pharmaceutics, 439(1), 275-285 (2012)

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