36825-36-2

Basic information

• Product Name: 4-Amino-3-bromoquinoline
• Synonyms: 4-AMINO-3-BROMOQUINOLINE;3-BROMO-QUINOLIN-4-YLAMINE;3-bromo-4-aminoquinoline;3-broMoquinolin-4-aMine
• CAS NO: 36825-36-2
• Molecular Formula: C₉H₇BrN₂
• Molecular Weight: 223.07
• EINECS: -0
• Mol File: 36825-36-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 203°C
• Boiling Point: 346.8 °C at 760 mmHg
• Flash Point: 163.5 °C
• Appearance: /
• Density: 1.6051 (rough estimate)
• Vapor Pressure: 5.61E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 4-Amino-3-bromoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3-bromoquinoline(36825-36-2)
• EPA Substance Registry System: 4-Amino-3-bromoquinoline(36825-36-2)

Safety Data

• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 36825-36-2(Hazardous Substances Data)

Usage

Uses

4-Amino-3-bromoquinoline is a useful research intermediate for the preparation of aminoquinolines.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 43, p. 4667, 2000 DOI: 10.1021/jm0002073

InChI:InChI=1/C9H7BrN2/c10-7-5-12-8-4-2-1-3-6(8)9(7)11/h1-5H,(H2,11,12)

Upstream product

• 578-68-7 4-aminoquinoline 
• 10035-10-6 hydrogen bromide 
• 56-57-5 4-nitroquinoline-N-oxide 
• 4363-95-5 quinoline-4-carboxamide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 67-66-3 chloroform 

Downstream Products

• 5332-24-1 3-bromoquinoline 

Relevant articles and documents

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Synthetic method of 4-amino-6-nitro-3-bromoquinoline

The invention relates to 4-amino-6-nitro-3-bromoquinoline that is a precursor for preparing nociceptin antagonists. The invention discloses a synthetic method of 4-amino-6-nitro-3-bromoquinoline. The synthetic method comprises the following steps: carrying out iron powder reduction reaction on 4-nitroquinoline-N-oxide, as a raw material, in the presence of acetic acid, so as to generate 4-aminoquinoline; carrying out bromination reaction, so as to generate 4-amino-3-bromoquinoline; finally carrying out nitration reaction, so as to generate 4-amino-6-nitro-3-bromoquinoline. The compound structure of 4-amino-6-nitro-3-bromoquinoline is represented by 1H-NMR, 13C-NMR and IR. The adopted raw materials and reagents are cheap and easily available, the synthetic method is simple and feasible, and reaction conditions are mild; according to the synthetic method, a simple and convenient synthetic way is developed for the synthesis of 4-amino-6-nitro-3-bromoquinoline compounds.

4-Aminoquinolines: Novel nociceptin antagonists with analgesic activity

Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure - Activity relationships eventually led to the optimum compounds. One of these compounds, N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from μ-opioid agonists.