5690-24-4

Basic information

• Product Name: 1,4,5,8-NAPHTHALENETETRACARBOXDIIMIDE
• Synonyms: Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone;NAPHTHALENE-1,4,5,8-TETRACARBOXYLIC DIIMIDE;1,4,5,8-NAPHTHALENETETRACARBONDIIMIDE;1,4,5,8-NAPHTHALENETETRACARBOXDIIMIDE;1,4,5,8-NAPHTHALENETETRACARBOXYLIC DIIMIDE;naphthalene-1,8:4,5-tetracarboxydiimide;1,4,5,8-NAPHTHALENETETRACARBOXDIIMIDE 98+%;1,4,5,8-NAPHTHALENETERTACARBOXDIIMIDE
• CAS NO: 5690-24-4
• Molecular Formula: C₁₄H₆N₂O₄
• Molecular Weight: 266.21
• EINECS: 227-159-0
• Product Categories: Acid Anhydrides, etc. (Reagents for Conducting Polymer Research);Functional Materials;Reagents for Conducting Polymer Research
• Mol File: 5690-24-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: >410 °C
• Boiling Point: 702.8°Cat760mmHg
• Flash Point: 311.1°C
• Appearance: /
• Density: 1.666g/cm³
• Vapor Pressure: 1.33E-19mmHg at 25°C
• Refractive Index: 1.77
• PKA: 7.98±0.20(Predicted)
• CAS DataBase Reference: 1,4,5,8-NAPHTHALENETETRACARBOXDIIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,5,8-NAPHTHALENETETRACARBOXDIIMIDE(5690-24-4)
• EPA Substance Registry System: 1,4,5,8-NAPHTHALENETETRACARBOXDIIMIDE(5690-24-4)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 5690-24-4(Hazardous Substances Data)

Usage

General Description

1,4,5,8-Naphthalenetetracarboxdiimide is a chemical compound with the molecular formula C14H4N2O6. It is a synthetic organic compound that is commonly used as a blue pigment in dyes and inks. 1,4,5,8-Naphthalenetetracarboxdiimide is also used as a precursor in the production of other chemicals and materials. It has been studied for its potential applications in organic semiconductors and as a building block for the synthesis of complex organic molecules. However, it is important to handle this chemical with care, as it is classified as a hazardous substance and should be used in accordance with safety guidelines and regulations.

InChI:InChI=1/C14H6N2O4/c17-11-5-1-2-6-10-8(14(20)16-12(6)18)4-3-7(9(5)10)13(19)15-11/h1-4H,(H,15,17,19)(H,16,18,20)

Upstream product

• 858436-00-7 4,8-dichloro-naphthalene-1,5-dicarboxylic acid 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 7664-41-7 ammonia 
• 1825-30-5 1,5-dichloronaphthalene 

Downstream Products

• 34151-51-4 N,N’-bis(4-pyridylmethyl)-1,4,5,8-naphthalenetetra-carboxydiimide 
• 1246286-32-7 (((1,3,6,8-tetraoxobenzo[lmn][3,8]phenanthroline-2,7(1H,3H,6H,8H)-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate) 
• 910138-52-2 (R)-2-[7-((R)-1-carboxy-2-tritylsulfanyl-ethyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl]-3-tritylsulfanyl-propionic acid 
• 828301-12-8 [S,S]-N,N'-bis-[4-(benzyloxycarbonyl)-2-(N-5-fluoro-2,4-dinitrophenylamino)-butanoyl]-2,7-diaza-1,2,3,6,7,8-hexahydropyrene 
• 828301-11-7 [S,S]-N,N'-bis-[3-(benzyloxycarbonyl)-2-(N-5-fluoro-2,4-dinitrophenylamino)-propionyl]-2,7-diaza-1,2,3,6,7,8-hexahydropyrene 
• 828301-09-3 [S,S]-N,N'-bis-[4-(benzyloxycarbonyl)-2-(N-t-butoxycarbonylamino)-butanoyl]-2,7-diaza-1,2,3,6,7,8-hexahydropyrene 

Relevant articles and documents

A facile synthesis of 2,7-diazapyrene

2,7-Diazapyrene is synthesized in three high-yield steps from commercially available 1,4,5,8-naphthalene tetracarboxylic dianhydride, which first reacts with concentrated ammonium hydroxide solution at room temperature to give 1,4,5,8-naphthalenetetracarboxylic diimide (96%). The latter compound is subsequently reduced with borane in refluxing tetrahydrofuran to give 1,2,3,6,7,8-hexahydro-2,7-diazapyrene (77%), which in turn is oxidized with manganese dioxide in refluxing benzene giving 2,7-diazapyrene (71%).

Molecular Orientation Change in Naphthalene Diimide Thin Films Induced by Removal of Thermally Cleavable Substituents

The potential of naphthalene-1,8:4,5-tetracarboxylic diimide (NDI-H) as a transparent electron-transporting material was examined. A soluble precursor was designed and synthesized having two tert-butoxycarbonyl solubilizing substituents at the imide moieties. This precursor molecule, NDI-Boc, is converted to the hydrogen-substituted NDI-H by heating the spin-coated precursor films. The molecular orientation during the thermal conversion of NDI-Boc to NDI-H was examined using two-dimensional grazing incidence X-ray diffraction (2D-GIXD) and p-polarized multiple-angle incidence resolution spectrometry. It was revealed that, driven by the formation of intermolecular hydrogen bonds, the molecular orientation changes from tilted edge-on to face-on orientation. In situ 2D-GIXD measurements confirmed that the change of molecular orientation is simultaneously caused by the cleaving of the Boc substituents. Time-resolved microwave conductivity measurements were used to show that the resulting NDI-H film has anisotropic charge-carrier transport with preferential mobility in the direction perpendicular to the film plane. We fabricated perovskite solar cells to demonstrate that the NDI-H film effectively functions as the bottom electron-transporting layer in these devices.

The reductive aromatization of naphthalene diimide: A versatile platform for 2,7-diazapyrenes

The reductive aromatization of naphthalene diimide provides tetrapivaloxy-2,7-diazapyrene, which serves as a versatile platform toward peripherally substituted 2,7-diazapyrenes. Time-resolved microwave conductivity measurements demonstrated that the intrinsic electron mobility of 2,7-diazapyrene is significantly higher than that of the corresponding pyrene.

NEW ANTI-CLOSTRIDIUM COMPOUNDS

The present invention relates to compounds having a backbone structure for use as antibiotic, more specifically use against infections with Gram positive bacteria, preferably Clostridium, more preferably C. difficile or C. perfringens. The compounds of the invention are particularly useful against spores of these bacteria.