74924-94-0

Basic information

• Product Name: 2-Amino-4-bromonaphthalene
• Synonyms: 2-Amino-4-bromonaphthalene;4-BroMonaphthalen-2-aMine;4-Bromo-2-naphthalenamine
• CAS NO: 74924-94-0
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08122
• Mol File: 74924-94-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 70-71 °C
• Boiling Point: 360.7±15.0 °C(Predicted)
• Appearance: /
• Density: 1.563±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.33±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4-bromonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-bromonaphthalene(74924-94-0)
• EPA Substance Registry System: 2-Amino-4-bromonaphthalene(74924-94-0)

Safety Data

• Hazardous Substances Data: 74924-94-0(Hazardous Substances Data)

Usage

Description

2-Amino-4-bromonaphthalene is an organic compound characterized by the presence of an amino group attached to the 2nd carbon and a bromine atom at the 4th position of the naphthalene ring. This halogenated aromatic amine serves as a key intermediate in the synthesis of various organic compounds and materials.
Used in Organic Synthesis:
2-Amino-4-bromonaphthalene is used as a building block for the synthesis of azaphenanthrene derivatives, which are important in the development of organic electroluminescent device materials. These derivatives exhibit unique photophysical and electronic properties, making them suitable for applications in optoelectronics, such as organic light-emitting diodes (OLEDs) and other light-emitting technologies.
Used in Optoelectronics Industry:
In the optoelectronics industry, 2-Amino-4-bromonaphthalene is used as a precursor for the preparation of azaphenanthrene derivatives. These derivatives are employed in the fabrication of organic electroluminescent devices due to their favorable properties, such as high quantum efficiency, tunable emission colors, and good stability. This contributes to the advancement of energy-efficient and eco-friendly lighting and display technologies.

Upstream product

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Downstream Products

• 5498-31-7 4-bromo-naphthalen-2-ol 
• 51671-06-8 1-bromo-3-chloronaphthalene 
• 52358-73-3 1,3-dibromonaphthalene 
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• 3799-79-9 2-(3-Fluor-naphthoyl-⁽¹⁾)-benzoesaeure 
• 147397-60-2 3-methoxy-1-naphthoic acid 
• 147397-59-9 1-cyano-3-methoxynaphthalene 
• 1578179-15-3 2-(4-iodonaphthalen-2-ylamino)-5-nitrobenzoic acid 
• 228107-17-3 3-amino-1-phenylnaphthalene 

Relevant articles and documents

A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)

A novel type of chiral redox disulfonate iron complex for asymmetric catalysis is reported. The [Fe((Ra)-BINSate)]+(BINSate = 1,1′-binaphthalene-2,2′-disulfonate) complex effectively promotes the enantioselective oxidative cross-coupling between 2-naphthols (1) and 2-aminonaphthalene derivatives (2), affording optically enriched (Ra)-2-amino-2′-hydroxy-1,1′-binaphthyls (NOBINs) with exceptional yields and enantioselective ratios (up to 99% yield and 96:4 er). The [Fe((Ra)-BINSate)]+catalyst was designed as a chiral version of FeCl3with multicoordination sites available for binding the two coupling partners 1 and 2 as well as the oxidant. Our structure-selectivity and activity study, which covered most of the important positions in the NOBIN scaffold, revealed the effect of different substitution patterns on the coupling efficiency and stereoselectivity.

Monna, a potent and selective blocker for transmembrane protein with unknown function 16/anoctamin-1

Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established (Oh et al., 2008). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a-NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC 5050 of 0.08 μM for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10～30 μM MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia.