613-76-3

Basic information

• Product Name: naphthalene-2,7-diamine
• Synonyms: naphthalene-2,7-diamine;2,7-Naphthylenediamine;NSC 356142
• CAS NO: 613-76-3
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.1998
• EINECS: 210-353-4
• Mol File: 613-76-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 166-167℃
• Boiling Point: 395.7°C at 760 mmHg
• Flash Point: 230.8°C
• Appearance: /
• Density: 1.234g/cm³
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.68±0.10(Predicted)
• CAS DataBase Reference: naphthalene-2,7-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: naphthalene-2,7-diamine(613-76-3)
• EPA Substance Registry System: naphthalene-2,7-diamine(613-76-3)

Safety Data

• Hazardous Substances Data: 613-76-3(Hazardous Substances Data)

Usage

General Description

Naphthalene-2,7-diamine is an organic compound with the chemical formula C10H10N2. It is also known as 2,7-diaminonaphthalene and is a derivative of naphthalene. The compound is a yellow crystalline solid that is soluble in organic solvents but insoluble in water. It is primarily used in the production of dyes and pigments, as well as in the synthesis of pharmaceuticals and other organic compounds. Naphthalene-2,7-diamine has also been studied for its potential use in the development of new materials for electronic and optoelectronic applications. However,

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

Upstream product

• 582-17-2 2,7-Dihydroxynaphthalene 
• 24824-27-9 2,7-dinitronaphthalene 
• 93-36-7 2-amino-7-hydroxynaphthalene 
• 7664-41-7 ammonia 
• 7647-01-0 hydrogenchloride 
• 7772-99-8 stannous chloride 
• 68828-45-5 1-((2,7-dihydroxynaphthalen-8-yl)methyl)naphthalene-2,7-diol 

Downstream Products

• 93-36-7 2-amino-7-hydroxynaphthalene 
• 103393-75-5 1,2,3,4-tetrahydronaphthalene-2,7-diamine 
• 118477-42-2 2,7-di(p-toluenesulfonamido)naphthalene 
• 58556-77-7 2,7-diiodonaphthalene 
• 95957-80-5 N,N'-(1-bromo-naphthalene-2,7-diyl)-bis-toluene-4-sulfonamide 
• 113750-31-5 N,N'-(1,8-dichloro-naphthalene-2,7-diyl)-bis-toluene-4-sulfonamide 
• 115188-28-8 N,N'-(1,1,8,8-tetrachloro-1H,8H-naphthalene-2,7-diylidene)-bis-toluene-4-sulfonamide 
• 95139-29-0 2,7-diphenylnaphthalene 
• 777843-08-0 methyl 3-{[(7-amino-2-naphthyl)amino]sulfonyl}benzoate 
• 1260632-55-0 N⁽¹⁾,N⁽¹⁾'-((naphthalene-2,7-diylbis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(N⁽³⁾-(2-ethylhexyl)-4,6-bis((2-ethylhexyl)oxy)isophthalamide) 
• 1260632-47-0 N⁽¹⁾-(2-((7-acetamidonaphthalen-2-yl)amino)-2-oxoethyl)-N⁽³⁾-(2-ethylhexyl)-4,6-bis((2-ethylhexyl)oxy)isophthalamide 

Relevant articles and documents

Characterization of Push-Pull-Type Benzo[X]quinoline Derivatives (X = g or f): Environmentally Responsive Fluorescent Dyes with Multiple Functions

Benzo[X]quinoline (X = g or f: BQX) derivatives bearing bis-trifluoromethyl and amine groups have been designed as push-pull-type fluorescent dyes. Through the synthesis of BQX derivatives from 2,7-diaminonaphthalene, linear-type (BQL) and angular-type (BQA) structural isomers were obtained. X-ray structures of single crystals from six given BQX derivatives revealed that the BQL and BQA series adopt planar- and bowl-shaped structures. In the fluorescence spectra, interestingly, the BQL series emitted in the near-infrared region over 700 nm in polar solvents. Based on the visible absorptions and base properties related to the amine moiety, the ammonia responsiveness was investigated using an ion-exchange reaction by the BQX-HCl salt. By exploiting the environmentally responsive fluorescence probe, cell imaging through confocal laser microscopy was conducted using HeLa and 3T3-L1 cells, emitting specific lipid droplets. The results indicate that BQX derivatives have multiple functions and may be applied in materials chemistry and biochemistry.

Rhodium-catalyzed asymmetric hydrogenation of olefins with PhthalaPhos, a new class of chiral supramolecular ligands

A library of 19 binol-derived chiral monophosphites that contain a phthalic acid diamide group (Phthala- Phos) has been designed and synthesized in four steps. These new ligands were screened in the rhodium-catalyzed enantioselective hydrogenation of prochiral dehydroamino esters and enamides. Several members of the library showed excellent enantioselectivity with methyl 2-acetamido acrylate (6 ligands gave >97% ee), methyl (Z)-2- acetamido cinnamate (6 ligands gave >94% ee), and N-(1-phenylvinyl)acetamide (9 ligands gave >95% ee), whilst only a few representatives afforded high enantioselectivities for challenging and industrially relevant substrates N-(3,4-dihydronaphthalen-1- yl)-acetamide (96% ee in one case) and methyl (E)-2-(acetamidomethyl)-3- phenylacrylate (99% ee in one case). In most cases, the new ligands were more active and more stereoselective than their structurally related monodentate phosphites (which are devoid of functional groups that are capable of hydrogen-bonding interactions). Control experiments and kinetic studies were carried out that allowed us to demonstrate that hydrogen-bonding interactions involving the diamide group of the PhthalaPhos ligands strongly contribute to their outstanding catalytic properties. Computational studies carried out on a rhodium precatalyst and on a conceivable intermediate in the hydrogenation catalytic cycle shed some light on the role played by hydrogen bonding, which is likely to act in a substrate-orientation effect.

Intramolecular interactions in diiodonaphthalenes

The synthesis and the electronic structure of isomeric di-iodonaphthalenes is described. The electronic structure has been investigated by HeI/HeII photoelectron spectroscopy and non-Koopmans' quantum chemical calculations. The influence of the topology of iodine substitution on the electronic structure is discussed. Special emphasis is placed on elucidating the role of intramolecular iodine-iodine interactions.