2243-61-0

Basic information

• Product Name: 1,4-DIAMINONAPHTHALENE
• Synonyms: 1,4-NAPHTHALENEDIAMINE;1,4-DIAMINONAPHTHALENE;naphthalene-1,4-diamine;1,4-Naphthylenediamine;(4-amino-1-naphthyl)amine;(4-amino-1-naphthyl)amine(SALTDATA: 2HCl);(4-aMino-1-naphthyl)aMine dihydrochloride (SALTDATA: 2HCl);1,4-Diaminonaphthalene 97%
• CAS NO: 2243-61-0
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.2
• EINECS: 218-816-2
• Mol File: 2243-61-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: 114-116 °C
• Boiling Point: 273.29°C (rough estimate)
• Flash Point: 211.5 °C
• Appearance: /
• Density: 1.1192 (rough estimate)
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: 1.6441 (estimate)
• PKA: 5.72±0.10(Predicted)
• CAS DataBase Reference: 1,4-DIAMINONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIAMINONAPHTHALENE(2243-61-0)
• EPA Substance Registry System: 1,4-DIAMINONAPHTHALENE(2243-61-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: QJ3380000
• Hazardous Substances Data: 2243-61-0(Hazardous Substances Data)

Usage

General Description

Dark green to black crystalline solid.

Air & Water Reactions

1,4-DIAMINONAPHTHALENE may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

1,4-DIAMINONAPHTHALENE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for 1,4-DIAMINONAPHTHALENE are not available; however, 1,4-DIAMINONAPHTHALENE is probably combustible.

InChI:InChI=1/C10H10N2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H,11-12H2

Upstream product

• 3713-23-3 4-(4-amino-naphthalen-1-ylazo)-benzenesulfonic acid 
• 131-22-6 4-phenylazo-1-naphthylamine 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 2835-61-2 4-(1-naphthalenylazo)-1-naphthalenamine 
• 4171-46-4 bis-(4-nitro-[1]naphthyl)-diazene 
• 10034-85-2 hydrogen iodide 
• 64-19-7 acetic acid 
• 6357-89-7 1,4-diamino-naphthalene-2-sulfonic acid 
• 7782-99-2 sulphurous acid 
• 88246-92-8 5,8-diaminonaphthalene-1-sulfonic acid 
• 23939-67-5 [1,4]naphthoquinone-bis-chlorimin 
• 74217-45-1 4-(4-Amino-[1]naphthylazo)-phenol 

Downstream Products

• 130-15-4 [1,4]naphthoquinone 
• 1359988-18-3 N,N'-bis[1-(2-(dimesitylboranyl)phenyl)meth-(E)-ylidene]-naphthalene-1,4-diamine 
• 1567836-16-1 diethyl 2,2′-(naphthalene-1,4-diylbis(((4-methoxyphenyl)sulfonyl)azanediyl))diacetate 
• 1567836-15-0 2,2′-(naphthalene-1,4-diylbis(((4-methoxyphenyl)sulfonyl)azanediyl))diacetic acid 

Relevant articles and documents

Unravelling the mechanism of cobalt-catalysed remote C-H nitration of 8-aminoquinolinamides and expansion of substrate scope towards 1-naphthylpicolinamide

Previously, an unexpected Co-catalysed remote C-H nitration of 8-aminoquinolinamide compounds was developed. This report provided a novel reactivity for Co which was assumed to proceed through the mechanistic pathway already known for analogous Cu-catalysed remote couplings of the same substrates. In order to shed light into this intriguing, and previously unobserved reactivity for Co, a thorough computational study has now been performed, which has allowed for a full understanding of the operative mechanism. This study demonstrates that the Co-catalysed remote coupling does not occur through the previously proposed Single Electron Transfer (SET) mechanism, but actually operates through a high-spin induced remote radical coupling mechanism, through a key intermediate with significant proportion of spin density at the 5- and 7-positions of the aminoquinoline ring. Additionally, new experimental data provides expansion of the synthetic utility of the original nitration procedure towards 1-naphthylpicolinamide which unexpectedly appears to operate via a subtly different mechanism despite having a similar chelate environment.

Design, Synthesis, and Initial Evaluation of Affinity-Based Small-Molecule Probes for Fluorescent Visualization and Specific Detection of Keap1

Keap1 is a pluripotent protein which plays a predominant role in cellular homeostasis and stress responses. Given that the cellular environment is quite dynamic and versatile, further investigation of the function of Keap1 depends on tools for specific and real-time detection of Keap1. Herein, we report the development of functional affinity-based small-molecule probes which can overcome some shortcomings of current methods and be applied in further studying the function of Keap1.

Keap1-Nrf2 PPI inhibitor prodrug and preparation method and application

The invention discloses a Keap1-Nrf2 PPI inhibitor prodrug and a preparation method and application. According to the prodrug P-168 provided by the invention, a polar carboxylic acid group of an active compound 168 is blocked, so that the fat solubility is improved, and the membrane permeability and druggability are effectively improved; the prodrug P-168 is reduced under the condition of high ROS, a pharmacophore 168 and a fluorophore coumarin are released, expression of Nrf2 and downstream genes of Nrf2 is activated, anti-inflammatory activity is brought into play, and meanwhile fluorescenceis released to achieve visual monitoring.

Optimization of 1,4-bis(arylsulfonamido)naphthalene-N,N'-diacetic acids as inhibitors of Keap1-Nrf2 protein-protein interaction to suppress neuroinflammation

The protein–protein interaction (PPI) between kelch-like ECH-associated protein 1 (Keap1) and nuclear factor erythroid 2-related factor 2 (Nrf2) is recognized as a promising target for the prevention and treatment of oxidative stress-related inflammatory diseases. Herein, a series of novel 1,4-bis(arylsulfonamido)naphthalene-N,N'-diacetic acid analogs (7p-t and 8c) were designed to further explore the structure–activity relationships of the series. Their activities were measured first with a fluorescence polarization (FP) assay and more potent compounds were further evaluated using a more sensitive time-resolved fluorescence energy transfer (TR-FRET) assay, demonstrating IC50 values between 7.2 and 31.3 nM. In cytotoxicity studies, the naphthalene derivatives did not show noticeable toxicity to human HepG2-C8 and mouse brain BV-2 microglia cells. Among them, compound 7q bearing oxygen-containing fused rings was shown to significantly stimulate the cellular Nrf2 signaling pathway, including activation of antioxidant response element (ARE)-controlled expression of Nrf2 target genes and proteins. More importantly, 7q suppressed up-regulation of several pro-inflammatory cytokines in lipopolysaccharide (LPS)-challenged BV-2 microglial cells, representing a potential therapeutic application for controlling neuroinflammatory disorders.