50358-63-9

Basic information

• Product Name: 5-Bromoquinoxalin-6-amine
• Synonyms: 6-Amino-5-bromoquinoxaline ,98%;5-BroMoquinoxalin-6-aMine, 6-AMino-5-broMoquinoxaline;Brimonidine Related Compound (5-Bromo-6-Aminoquinoxaline);6-AMINO-5-BROMOQUINOXALINE;5-BROMO-6-QUINOXALINAMINE;5-bromoquinoxalin-6-amine;6-Amino-5-bromoquinoxaline 98%;5-Bromo-6-aminoquinoxaline
• CAS NO: 50358-63-9
• Molecular Formula: C₈H₆BrN₃
• Molecular Weight: 224.06
• EINECS: 1592732-453-0
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Quinolines, Isoquinolines & Quinoxalines;Halides;Quinolines, Isoquinolines & Quinoxalines;Chemical Amines;Amines
• Mol File: 50358-63-9.mol

Chemical Properties

• Melting Point: 151-153°C
• Boiling Point: 367 °C at 760 mmHg
• Flash Point: 175.8 °C
• Appearance: yellow solid
• Density: 1.744 g/cm³
• Vapor Pressure: 1.4E-05mmHg at 25°C
• Refractive Index: 1.747
• Storage Temp.: Refrigerator
• PKA: 0.33±0.30(Predicted)
• CAS DataBase Reference: 5-Bromoquinoxalin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoquinoxalin-6-amine(50358-63-9)
• EPA Substance Registry System: 5-Bromoquinoxalin-6-amine(50358-63-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 50358-63-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromoquinoxalin-6-amine is used as an active pharmaceutical ingredient for the development of antiglaucoma agents, specifically in the formulation of brimonidine tartrate ophthalmic solution with a concentration of 0.15%. It helps in reducing intraocular pressure in the eyes, providing relief from glaucoma and other eye conditions characterized by high pressure within the eye.
Used in Research and Development:
As a metabolite of Brimonidine, 5-Bromoquinoxalin-6-amine may also be used in research and development for understanding the pharmacological effects, metabolism, and potential applications of Brimonidine and its derivatives in various medical fields. This can contribute to the discovery of new drugs and therapies for different health conditions.

InChI:InChI=1/C8H6BrN3/c9-7-5(10)1-2-6-8(7)12-4-3-11-6/h1-4H,10H2

Upstream product

• 6298-37-9 6-aminoquinoxaline 
• 6639-87-8 6-nitroquinoxaline 
• 99-56-9 4-Nitrophenylene-1,2-diamine 

Relevant articles and documents

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Preparation method of brimonidine intermediate

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of a brimonidine intermediate. The method for preparing the brimonidine intermediate comprises the following steps: by taking 6-amino quinoxaline as a raw material and HBr as a bromine source, carrying out oxidative bromination in the presence of O2 through the action of a copper catalyst to prepare the brimonidine intermediate 5-bromo-6-amino quinoxaline. The method provided by the invention has the advantages of cheap and easily available reaction raw materials, mild reaction conditions, simple operation process, high product yield, high purity and high atom utilization rate, and is more suitable for industrial production.

Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines

A series of 29 new quinoxalines was synthesized and evaluated in vitro against several parasites (Leishmania donovani, Trypanosoma brucei brucei, and Trichomonas vaginalis). Several of them displayed interesting activities, and particularly four quinoxaline amides showed in vitro antileishmanial properties (IC50 less than 20 μM).

Methods of preventing and reducing the severity of stress-associated conditions

The present invention provides a method of preventing or reducing the severity of a stress-associated condition in a subject by systemically administering to the subject an effective amount of brimonidine or a pharmaceutically acceptable salt, ester, amide, sterioisomer or racemic mixture thereof. Stress-associated conditions that can be treated according to a method of the invention include, but are not limited to, dyspepsia, tachycardias other than tachycardia associated with myocardial ischemia, panic attack, non-inflammatory dermatogical conditions, disorders of muscle contraction, sensory hypersensitivity associated with migraine, and behavioral disorders.

Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives

A method of treating a mammal comprises administering to a mammal an effective amount to provide a desired therapeutic effect in the mammal of a compound selected from the group consisting of those having the formula: and pharmaceutically acceptable acid addition salts thereof and mixtures thereof, wherein R1and R2each is selected from the group consisting of alkyl radicals containing 1 to 4 carbon atoms and alkoxy radicals containing 1 to 4 carbon atoms, the 2-imidazolin-2-ylamino group may be in any of the 5-, 6-, 7- or 8-positions of the quinoxaline nucleus, and R3, R4and R5each is located in one of the remaining 5-, 6-, 7- or 8-positions of the quinoxaline nucleus and is independently selected from the group consisting of Cl, Br, H and alkyl radicals containing 1 to 3 carbon atoms. Such compounds, when administered to a mammal, provide desired therapeutic effects, such as reduction in peripheral pain.

METHODS FOR USING (2-IMIDAZOLIN-2-YLAMINO) QUINOXALINE DERIVATIVES

A method of treating a mammal comprises administering to a mammal an effective amount to provide a desired therapeutic effect in the mammal of a compound selected from the group consisting of those having the formula: STR1 and pharmaceutically acceptable acid addition salts thereof and mixtures thereof, wherein R 1 and R 2 each is independently selected from the group consisting of alkyl radicals containing 1 to 4 carbon atoms and alkoxy radicals containing 1 to 4 carbon atoms, the 2-imidazolin-2-ylamino group may be in any of the 5-, 6-, 7-or 8-positions of the quinoxaline nucleus, and R 3, R 4 and R 5 each is located in one of the remaining 5-, 6-, 7-or 8-positions of the quinoxaline nucleus and is independently selected from the group consisting of Cl, Br, H and alkyl radicals containing 1 to 3 carbon atoms. Such compounds, when administered to a mammal, provide treatment for ischemia.

Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives

A method of treating a mammal comprises administering to a mammal an effective amount to provide a desired therapeutic effect in the mammal of a compound selected from the group consisting of those having the formula: STR1 , pharmaceutically acceptable acid addition salts thereof and mixtures thereof, wherein R1 and R4 are independently selected from the group consisting of H and alkyl radicals having 1 to 4 carbon atoms; the R2 s are independently selected from H or alkyl radicals having 1 to 4 carbon atoms or are, together, oxo; the R3 s are independently selected from H or alkyl radicals having 1 to 4 carbon atoms or are, together, oxo; the 2-imidazolin-2-ylamino group may be in any of the 5-, 6, 7- or 8- positions of the quinoxaline nucleus; and R5, R6 and R7 each is located in one of the remaining 5-, 6-, 7- or 8- positions of the quinoxaline nucleus and is independently selected from the group consisting of Cl, Br, H and alkyl radicals having 1 to 3 carbon atoms. Such compounds, when administered to a mammal, provide desired therapeutic effects, such as constriction of one or more blood vessels and decongestion of one or more nasal passages.

METHODS FOR USING (2-IMIDAZOLIN-2-YLAMINO) QUINOXALINE DERIVATIVES

A method of treating a mammal comprises administering to a mammal an effective amount to provide a desired therapeutic effect in the mammal of a compound selected from the group consisting of those having the formula: STR1 ,pharmaceutically acceptable acid addition salts thereof and mixtures thereof, wherein R 1 and R 4 are independently selected from the group consisting of H and alkyl radicals having 1 to 4 carbon atoms; the R 2 s are independently selected from H or alkyl radicals having 1 to 4 carbon atoms or are, together, oxo; the R 3 s are independently selected from H or alkyl radicals having 1 to 4 carbon atoms or are, together, oxo; the 2-imidazolin-2-ylamino group may be in any of the 5-, 6, 7-or 8-positions of the quinoxaline nucleus; and R 5, R 6 and R 7 each is located in one of the remaining 5-, 6-, 7-or 8-positions of the quinoxaline nucleus and is independently selected from the group consisting of Cl, Br, H and alkyl radicals having 1 to 3 carbon atoms. Such compounds, when administered to a mammal, provide desired therapeutic effects, such as reduction in peripheral pain, anesthetization of the central nervous system, constriction of one or more blood vessels, reduction in or prevention of at least one effect of ischemia, decongestion of one or more nasal passages, and reduction of at least one effect of an inflammatory disorder.

Method for using (2-imidazolin-2-ylamino) quinoxalines to reduce or maintain intraocular pressure

Certain (2-imidazolin-2-ylamino) quinoxalines are disclosed. Such quinoxalines reduce or maintain intraocular pressure when administered directly to the eye of a mammal.

(2-imidazolin-2-ylamino) tetrahydroquinoxalines and methods for using same

A compound selected from the group consisting of those having the formula: STR1 and pharmaceutically acceptable acid addition salts thereof, wherein R1 wherein R1 and R4 are independently selected from the group consisting of H and alkyl radicals containing 1 to 4 carbon atoms, R2 and R3 are independently selected from the group consisting of H, OXO, and alkyl radicals containing 1 to 4 carbon atoms, the 2-imidazolin-2-ylamino group may be in any of the 5-, 6-, 7- or 8- positions of the quinoxaline nucleus, and R5, R6 and R7 each is located in one of the remaining 5-, 6-, 7- or 8- positions of the qunioxaline nucleus and is selected from the group consisting of Cl, Br, H and alkyl radicals containing 1 to 3 carbon atoms. Such compounds, when administered to a mammal, provide desired therapeutic effects, such as alteration in the rate of fluid transport in the gastrointestinal tract, reduction in intraocular pressure, and increase in renal fluid flow.