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438626

Sigma-Aldrich

4-Hydroxy-3-nitrocoumarin

98%

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About This Item

Fórmula empírica (notación de Hill):
C9H5NO5
Número de CAS:
20261-31-8
Peso molecular:
207.14
MDL number:
MFCD00051671
UNSPSC Code:
12352100
PubChem Substance ID:
24867464
NACRES:
NA.22

assay

98%

mp

172 °C (dec.) (lit.)

SMILES string

OC1=C(C(=O)Oc2ccccc12)[N+]([O-])=O

InChI

1S/C9H5NO5/c11-8-5-3-1-2-4-6(5)15-9(12)7(8)10(13)14/h1-4,11H

InChI key

NZQAQAUWFHMVEM-UHFFFAOYSA-N

General description

4-Hydroxy-3-nitrocoumarin is a coumarin derivative and its cytotoxic action against cultured human tumor and normal cells has been investigated. It can be prepared by the nitration of 4-hydroxycoumarin in glacial acetic acid by using 72% HNO3.

Application

4-Hydroxy-3-nitrocoumarin may be used as starting reagent for the synthesis of following compounds:
  • 4-chloro-3-nitrocoumarin
  • 2-unsubstituted 3-nitrochromone
  • 4-amino-3-nitrocoumarins

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Synthesis of heteroannulated 3-nitro-and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone.
Iaroshenko VO, et al.
Tetrahedron, 68(11), 2532-2543 (2012)
Investigations of pyrans and related compounds.
Savel'ev VL, et al.
Chemistry of Heterocyclic Compounds, 9(7), 816-820 (1973)
Vidoslav Dekić et al.
Magnetic resonance in chemistry : MRC, 48(11), 896-902 (2010-09-08)
Herein, we describe the synthesis and complete assignment of the (1)H and (13)C NMR chemical shifts of a series of antimicrobial 4-arylamino-3-nitrocoumarin derivatives based on a combination of (1)H and (13)C NMR, (1)H-(1)H-COSY, NOESY, HSQC and HMBC experiments. Conformational effects
Biljana R Dekić et al.
Molecules (Basel, Switzerland), 15(4), 2246-2256 (2010-04-30)
Synthesis, spectral analysis and bioactivity of new coumarin derivatives are described in this paper. Eight new coumarin derivatives were synthesized in moderate to good yields by condensation of 4-chloro-3-nitrocoumarin and the corresponding heteroarylamine. The synthesized compounds were tested for their
Masami Kawase et al.
In vivo (Athens, Greece), 19(4), 705-711 (2005-07-08)
A preliminary exploration of coumarin derivatives as novel multidrug resistance (MDR) modulators was carried out to determine the basic features of the structure responsible for the MDR reversal activity. Among 44 coumarins, 14 compounds moderately induced the reversal of MDR
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