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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:
6642-29-1
Poids moléculaire :
243.17
Numéro Beilstein :
237909
Numéro CE :
229-659-4
Numéro MDL:
MFCD00013446
Code UNSPSC :
12162002
ID de substance PubChem :
24859437
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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Catégories apparentées

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
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

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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Certificats d'analyse (COA)

Lot/Batch Number
MKCG5236
MKBX4415V
MKBS5797V
MKBR2869V
04921JD

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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
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
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
Jun Yang et al.
Biotechnology and applied biochemistry, 66(1), 33-42 (2018-09-20)
A nitroreductase-encoded gene from an efficient nitro-reducing bacterium Streptomyces mirabilis DUT001, named snr, was cloned and heterogeneously expressed in Escherichia coli. The purified Streptomyces nitroreductase SNR was a homodimer with an apparent subunit molecular weight of 24 kDa and preferred NADH
Elizabeth A Jolley et al.
Biophysical chemistry, 239, 29-37 (2018-05-29)
DNA duplexes are stabilized by many interactions, one of which is stacking interactions between the nucleic acid bases. These interactions are useful for designing small molecules that bind to DNA. Naphthalimide intercalators have been shown to be valuable anti-cancer agents

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