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Sigma-Aldrich

4-Nitro-1,8-naphthalic anhydride

95%

Synonym(s):

4-Nitronaphthalene-1,8-dicarboxylic anhydride

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About This Item

Empirical Formula (Hill Notation):
C12H5NO5
CAS Number:
6642-29-1
Molecular Weight:
243.17
Beilstein/REAXYS Number:
237909
EC Number:
229-659-4
MDL number:
MFCD00013446
UNSPSC Code:
12162002
PubChem Substance ID:
24859437
NACRES:
NA.23

Quality Level

100

assay

95%

mp

226-229 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc2C(=O)OC(=O)c3cccc1c23

InChI

1S/C12H5NO5/c14-11-7-3-1-2-6-9(13(16)17)5-4-8(10(6)7)12(15)18-11/h1-5H

InChI key

LKOZHLXUWUBRDK-UHFFFAOYSA-N

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General description

4-Nitro-1,8-naphthalic anhydride is a yellow crystalline nitrocompound widely used in the field of dye synthesis and cellular imaging.

Application

4-Nitro-1,8-naphthalic anhydride can be used:
  • As a precursor to synthesize N-phenyl-amino-1,8-naphthalimide based fluorescent chemosensor to detect nitro-antibiotics at ppb level.
  • As a building block to synthesize shape memory polymers due to its ability to undergo Diels-Alder reaction
  • As a fluorochrome substrate for nitrogen reductase for noninvasive hypoxia imaging in cancer detection.
  • As a precursor to synthesize amphiphilic naphthalimide dyes with good color brilliancy.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Desislava Staneva et al.
Sensors (Basel, Switzerland), 20(12) (2020-06-25)
In this study, a novel 6-(allylamino)-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (NI3) was synthesized and characterized. Its copolymer with styrene was also obtained. The photophysical characteristics of NI3 were investigated in organic solvents and the results were compared with those of its structural analogue, 2-allyl-6-((2-(dimethylamino)ethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
Jin Zhou et al.
Chemistry, an Asian journal, 11(19), 2719-2724 (2016-02-09)
A lysosome-targeting fluorescent off-on probe has been developed by one-step synthesis for detecting lysosomal nitroreductase and hypoxia. The probe is constructed by incorporating morpholine (a lysosome-targeting unit) into 4-nitro-1,8-naphthalimide (as a fluorochrome and specific substrate for nitroreductase), and the detection
Naphthalimides in fluorescent imaging of tumor hypoxia ? An up-to-date review
Rashmi Kumari, et al.
Bioorganic Chemistry, 88, 102979-102979 (2019)
Awad I Said et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 196, 76-82 (2018-02-13)
A novel fluorescence sensing 1,8-naphthalimide fluorophore is synthesized and investigated. The novel probe comprising two different binding moieties is capable to detect selectively Fe3+ over the other representative metal ions as well as a combination of biologically important cations such
Discriminative fluorescent sensing of nitro-antibiotics at ppb level using N-phenyl-amino-1,8-naphthalimides chemosensors
Ananthu Shanmughan, et al.
Results in Chemistry, 4, 100546-100546 (2022)
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