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

Description

4-Amino-3-bromoquinoline is an organic compound with the molecular formula C9H7BrN2. It is characterized by the presence of an amino group (-NH2) at the 4th position and a bromine atom (Br) at the 3rd position on a quinoline ring. 4-Amino-3-bromoquinoline is known for its potential applications in the synthesis of various pharmaceuticals and chemical compounds.

Uses

Used in Pharmaceutical Research:
4-Amino-3-bromoquinoline is used as a research intermediate for the preparation of aminoquinolines. These aminoquinolines are important due to their wide range of biological activities, including antimalarial, antiprotozoal, and anticancer properties. The synthesis of these compounds often involves the use of 4-Amino-3-bromoquinoline as a key building block.
Used in Chemical Synthesis:
In addition to its applications in the pharmaceutical industry, 4-Amino-3-bromoquinoline is also utilized in the synthesis of various chemical compounds. Its unique structure allows for further functionalization and modification, making it a versatile starting material for the development of new molecules with potential applications in various fields.

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

• 56-57-5 4-nitroquinoline-N-oxide 
• 578-68-7 4-aminoquinoline 
• 10035-10-6 hydrogen bromide 
• 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.