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Sigma-Aldrich

4-Nitro-1,8-naphthalic anhydride

95%

Synonyme(s) :

4-Nitronaphthalene-1,8-dicarboxylic anhydride

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About This Item

Formule empirique (notation de Hill):
C12H5NO5
Numéro CAS:
Poids moléculaire :
243.17
Numéro Beilstein :
237909
Numéro CE :
Numéro MDL:
Code UNSPSC :
12162002
ID de substance PubChem :
Nomenclature NACRES :
NA.23

Pureté

95%

Pf

226-229 °C (lit.)

Chaîne SMILES 

[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

Clé InChI

LKOZHLXUWUBRDK-UHFFFAOYSA-N

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Description générale

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.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

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
Synthesis of disperse dyes derived from 4-amino-N-decyl-1, 8-naphthalimide and their dyeing properties on polyester fabrics
Umar Salami Ameuru, et al.
Dyes and Pigments, 157, 190-197 (2018)
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)
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

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