6492-86-0

Basic information

• Product Name: 4-Amino-1,8-naphthalic anhydride
• Synonyms: 6-AMINO-BENZO[DE]ISOQUINOLINE-1,3-DIONE;4-AMINO-1,8-NAPHTHALIC ANHYDRIDE;4-AMINO-1,8-NAPHTHALIMIDE;4-ANI;TIMTEC-BB SBB000529;TIMTEC-BB SBB003425;4-aminonaphthalene-1,8-dicarboxylic anhydride;6-Aminobenz[de]isochromene-1,3-dione
• CAS NO: 6492-86-0
• Molecular Formula: C₁₂H₇NO₃
• Molecular Weight: 212.2
• EINECS: 229-372-4
• Product Categories: Anhydride Monomers;Monomers;Polymer Science
• Mol File: 6492-86-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 360 °C
• Boiling Point: 501.4 °C at 760 mmHg
• Flash Point: 310.8 °C
• Appearance: Orange powder
• Density: 1.105 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.49E-10mmHg at 25°C
• Refractive Index: 1.77
• Storage Temp.: −20°C
• PKA: 1.15±0.20(Predicted)
• CAS DataBase Reference: 4-Amino-1,8-naphthalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-1,8-naphthalic anhydride(6492-86-0)
• EPA Substance Registry System: 4-Amino-1,8-naphthalic anhydride(6492-86-0)

Safety Data

• Hazard Codes: T
• Statements: 45-20/21/22-36/37/38
• Safety Statements: 53-22-26-36/37/39-45
• WGK Germany: 3
• RTECS: DE4081000
• Hazardous Substances Data: 6492-86-0(Hazardous Substances Data)

Usage

General Description

4-Amino-1,8-naphthalic anhydride, also known as 4-amino-1,8-naphthalimide, is a chemical compound with the molecular formula C12H7NO3. It is an organic compound that is commonly used as a building block in the synthesis of various dyes and pigments, such as fluorescent whitening agents and coloring agents for textiles and plastics. It is also used as a reagent in the preparation of pharmaceutical intermediates and other organic compounds. 4-Amino-1,8-naphthalic anhydride is a yellow to orange solid with a high melting point and limited solubility in water, and it should be handled and stored with caution due to its potential health and environmental hazards.

InChI:InChI=1/C12H7NO3/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(14)16-12(8)15/h1-5H,13H2

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 34087-02-0 2-nitro-1,8-naphthalic anhydride 
• 83-32-9 acenaphthene 
• 602-87-9 4-nitroacenaphthene 
• 6642-29-1 4-nitronaphthalic-1,8-anhydride 
• 7647-01-0 hydrogenchloride 
• 1262149-88-1 6-azido-1H,3H-benzo[de]isochromene-1,3-dione 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 

Downstream Products

• 1742-95-6 4-amino-1,8-naphthalimide 
• 34418-97-8 6-amino-2-benzyl-1Hbenzo[de]isoquinoline-1,3(2H)-dione 
• 34419-02-8 6-amino-2-methyl-1Hbenzo[de]isoquinoline-1,3(2H)-dione 

Relevant articles and documents

Reduction of 4-azidonaphthalimide with different phosphine ligands and exploration of their spectroscopic properties

A convenient, high efficient method for the reduction of 4-azidonaphthalimide to 4-aminonaphthalimide (1) by using PMe3 has been developed. Several 4-substituted 1,8-naphthalimide iminophosphoranes were also successfully synthesized. Their structures were characterized by NMR and MS analyses. The structures of compounds 2 and 3 were also confirmed by single crystal X-ray diffraction analysis. Their optoelectronic properties of these naphthalimides were investigated. The results indicated that their optical properties could be tuned by different phosphine ligands, which make them novel potential organic luminescent materials.

A GSH-responsive PET-based fluorescent probe for cancer cells imaging

An efficient PET-based probe, in which the ferrocene quencher and the naphthalimide fluorophore are linked by a disulfide bond, has been developed. This probe can be activated by GSH with fluorescence a turn-on response for blocking the PET process. In addition, it was successfully applied for distinguishing cancer cells from normal cells

Enhanced nonradiative decay in aqueous solutions of aminonaphthalimide derivatives via water-cluster formation

The photophysics of two derivatives of 4-aminonaphthalimide have been studied in aqueous, ethanolic, and mixed aqueous/ethanolic solvents, including both normal and deuterated solvents. It is found that the fluorescence quantum yield and lifetime both decrease with increased water content of the solvent and that this is entirely due to increased nonradiative decay, the radiative rate constant being virtually independent of the solvent composition. It is proposed that a mechanism involving the formation of a hydrogen-bonded water cluster is responsible for the observed behavior with the excitation energy of the naphthalimide being distributed amongst the stretching vibrations of the water cluster. The increase in the rate of nonradiative decay is greatly reduced in deuterated solvent mixtures in accord with Siebrand's theory of radiationless processes.

Distinguished Cys. Hcy And GSH naphthalimide fluorescent probe as well as preparation method and application thereof

The naphthalimide fluorescent probe can be used for distinguishing Cys, Hcy and GSH naphthalimide fluorescent probe as well as a preparation method and application thereof, and particularly relates to a fluorescence probe (Z1, Z2) for detecting a biological thiol through a urethane linker. The probe itself has blue fluorescence, emits yellow-green fluorescence with longer wavelength after the action of Cys and Hcy, and can realize distinguishing detection of Cys, Hcy and GSH. The fluorescent probe Z1, Z2 pairs Cys are high in action speed, strong in selectivity and high in sensitivity, can be used for detecting and imaging intracellular cysteine, and is simple in synthesis method, accessible in raw materials and easy to popularize.

A 4-aminonaphthalimide-based fluorescent traceable prodrug with excellent photoinduced cytotoxicity

A blue light activated anti-cancer prodrug, NST, was designed based on a photoactive 4-aminonaphthalimide derivative and an anticancer drug, 10-hydroxycamptothecin. NST was hard to be taken up by living cells and showed negligible dark cytotoxicity. The irradiation caused photocleavage of NST and resulted in high cytotoxicity.