24824-28-0

Basic information

• Product Name: 1,3-Naphthalenediamine(8CI,9CI)
• Synonyms: 1,3-Naphthalenediamine(8CI,9CI);1,3-diaminonaphthalene;1,3-Naphthalenediamine;2,4-Naphthalenediamine
• CAS NO: 24824-28-0
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.2
• Product Categories: BIPHENYL
• Mol File: 24824-28-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 390.1°C at 760 mmHg
• Flash Point: 226.7°C
• Appearance: /
• Density: 1.234g/cm³
• Vapor Pressure: 2.72E-06mmHg at 25°C
• Refractive Index: 1.757
• CAS DataBase Reference: 1,3-Naphthalenediamine(8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Naphthalenediamine(8CI,9CI)(24824-28-0)
• EPA Substance Registry System: 1,3-Naphthalenediamine(8CI,9CI)(24824-28-0)

Safety Data

• Hazardous Substances Data: 24824-28-0(Hazardous Substances Data)

Usage

General Description

1,3-Naphthalenediamine (8CI,9CI) is a chemical compound with the molecular formula C10H10N2. It is a dark colored crystalline solid that is insoluble in water. 1,3-Naphthalenediamine(8CI,9CI) is commonly used as a building block in the production of various dyes, pigments, and other chemical products. It is also used in the manufacturing of rubber additives, antioxidants, and pharmaceuticals. 1,3-Naphthalenediamine has been found to be toxic and may cause skin and eye irritation upon contact. It is important to handle this chemical with caution and to follow proper safety protocols when working with it.

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

Upstream product

• 3771-14-0 1-naphthol-3-sulfonic acid 
• 7664-41-7 ammonia 
• 132-86-5 1,3-dihydroxynaphthalene 
• 13029-24-8 2,4-dinitro-1-naphthalenamine 
• 52077-96-0 N-(2,4-dinitro-[1]naphthyl)-toluene-4-sulfonamide 
• 18271-17-5 N-tosyl-1-naphthylamine 
• 134-32-7 1-amino-naphthalene 
• 161393-72-2 1,3-dinitronaphthalen-4-yl trifluoromethanesulfonate 
• 13170-29-1 4-amino-naphthalene-2-sulfonic acid ; sodium salt 
• 7664-93-9 sulfuric acid 
• 872266-75-6 1,3-diamino-[2]naphthoic acid 
• 90923-80-1 4-Amino-[2]naphthol 
• 483349-25-3 (4-(tert-butoxycarbonylamino)-1-iodo-naphthalen-2-yl)carbamic acid tert-butyl ester 
• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 

Downstream Products

• 483349-31-1 5-allylamino-1-(chloromethyl)-3-[(2E)-3-(4-methoxyphenyl)-2-propenoyl]-1,2-dihydro-3H-benzo[e]indole 
• 204915-50-4 (2E)-1-[5-amino-1-(chloromethyl)-1H,2H,3H-benzo[e]indol-3-yl]-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media

1-Iodonaphthalene-2,4-diamines in trifluoroacetic acid/chloroform give stable Wheland-like tetrahedral cationic species observable by NMR, through an initial intramolecular protonation. Dynamic equilibria allow proton-deuterium exchange of aromatic protons and provide a mechanism for deiodination of 1-iodonaphthalene-2,4-diamines. The Royal Society of Chemistry.

One-scale basicities of diaminobenzenes and diaminonaphthalenes: from aniline to proton sponge

Basicity constants, pKa, for a wide range of mono-protonated diaminobenzenes and diaminonaphthalenes, including dimethylamino derivatives were for the first time uniformly measured in 20% aqueous ethanol (29 compounds) and 80% aqueous dioxane (39 compounds) spanning from aniline to 1,8-bis(dimethylamino)naphthalene (‘proton sponge’). The dioxane system proved to be more versatile and because of better solubility of N-alkylated polyaminoarenes allowed to add to the same scale some superbasic bis(dialkylamino)-, tetrakis(dialkylamino)-, and hexakis(dialkylamino)naphthalenes, thus extending the scale for almost 10 pKa units, revealing possible limits of basicity changes in aromatic amines. The basicity of reference bases, pyridine and triethylamine, was also measured in these solvent systems. A group of N-alkylated compounds was found to be less basic in aqueous dioxane when compared with their NH2-analogs. This anomaly was not observed in aqueous ethanol. Other basicity trends and correlations between different basicity scales were also discussed. Copyright

Probing the structural requirements of non-electrophilic naphthalene-based Nrf2 activators

Activation of the transcription factor Nrf2 has been posited to be a promising therapeutic strategy in a number of inflammatory and oxidative stress diseases due to its regulation of detoxifying enzymes. In this work, we have developed a comprehensive structure-activity relationship around a known, naphthalene-based non-electrophilic activator of Nrf2, and we report highly potent non-electrophilic activators of Nrf2. Computational docking analysis of a subset of the compound series demonstrates the importance of water molecule displacement for affinity, and the X-ray structure of di-amide 12e supports the computational analysis. One of the best compounds, acid 16b, has an IC50 of 61 nM in a fluorescence anisotropy assay and a Kd of 120 nM in a surface plasmon resonance assay. Additionally, we demonstrate that the ethyl ester of 16b is an efficacious inducer of Nrf2 target genes, exhibiting ex vivo efficacy similar to the well-known electrophilic activator, sulforaphane.