24241-18-7

Basic information

• Product Name: 2-Amino-3,5-dibromopyrazine
• Synonyms: 2-AMINO-3,5-DIBROMOPYRAZINE;3,5-DIBROMOPYRAZIN-2-YLAMINE;3,5-DIBROMOPYRAZINE-2-YLAMINE;3,5-DIBROMOPYRAZIN-2-AMINE;2-AMINO-3,5-DIBROMOPYRAZIN;3,5-dibromo-2-Pyrazinamine;3,5-dibromo-2-aminopyrazine;2-Amino-3,5-dibromopyrazine ,98%
• CAS NO: 24241-18-7
• Molecular Formula: C₄H₃Br₂N₃
• Molecular Weight: 252.89
• Product Categories: pharmacetical;Pyrazines;Chloropyrazines, etc.;Pyrazine;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrazinesHeterocyclic Building Blocks;amine| alkyl bromide
• Mol File: 24241-18-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 114-117 °C(lit.)
• Boiling Point: 294.6 °C at 760 mmHg
• Flash Point: 131.9 °C
• Appearance: Yellow to brown/Powder
• Density: 2.287 g/cm³
• Vapor Pressure: 0.00161mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• PKA: 0.81±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-3,5-dibromopyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3,5-dibromopyrazine(24241-18-7)
• EPA Substance Registry System: 2-Amino-3,5-dibromopyrazine(24241-18-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41
• Safety Statements: 26-36/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 24241-18-7(Hazardous Substances Data)

Usage

Description

2-Amino-3,5-dibromopyrazine is a white to light yellow crystalline compound that can be synthesized from 2-aminopyrazine through bromination using N-bromosuccinimide (NBS). It is a versatile intermediate in the synthesis of various organic compounds and has potential applications in different industries due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
2-Amino-3,5-dibromopyrazine is used as an intermediate in the preparation of various organic compounds, including 2-amino-5-bromopyrazin-3-thiol, 2-amino-3,5-bis(p-methoxyphenyl)-1,4-pyrazine, and 3,7-dihydroimidazo[1,2a]pyrazine-3-ones. Its reactivity and structural features make it a valuable building block for the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
2-Amino-3,5-dibromopyrazine is used as an intermediate in the preparation of rho kinase (ROCK) inhibitors, which are important targets for the development of drugs to treat various diseases, including cancer, cardiovascular diseases, and neurological disorders.
Used in Analytical Chemistry:
2-Amino-3,5-dibromopyrazine is used in the preparation of conjugated polymers for neurotoxin detection. Its unique chemical properties allow for the development of sensitive and selective sensors for the detection of neurotoxins, which are crucial for environmental monitoring and public health.

InChI:InChI=1/C4H3Br2N3/c5-2-1-8-4(7)3(6)9-2/h1H,(H2,7,8)

Upstream product

• 5049-61-6 2-Aminopyrazine 
• 886860-50-0 5-iodopyrazine-2-amine 

Downstream Products

• 6863-75-8 2-amino-5-bromopyrazine-3(4H)-thione 
• 125208-06-2 bromo-2 methyl-6 5H-pyrrolo<2,3-b>pyrazinecarboxylate-7 d'ethyle 
• 87597-21-5 ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate 
• 112342-70-8 6-bromo-2-ethoxycarbonylaminothiazolo/4,5-b/pyrazine 
• 63744-22-9 6,8-dibromoimidazo[1,2-a]pyrazine 
• 77112-66-4 2-amino-5-bromo-3-ethoxypyrazine 
• 77112-56-2 ethyl 6,8-dibromoimidazo<1,2-a>pyrazine-2-acetate 
• 87444-38-0 5-bromo-3-(methylthio)pyrazin-2-amine 
• 113305-95-6 3-aminopyrazine-2,6-dicarbonitrile 
• 17231-51-5 2-amino-5-bromo-3-cyanopyrazine 
• 55635-63-7 2-amino-5-bromo-3-(methylamino)pyrazine 
• 91225-40-0 5-bromo-3-hydrazinopyrazin-2-amine 
• 187973-44-0 3-(benzyloxy)-5-bromopyrazin-2-amine 
• 201812-53-5 3,5-Bis-phenylethynyl-pyrazin-2-ylamine 

Relevant articles and documents

Efficient Halogenation of 2-Aminopyrazine

2-Aminopyrazine was halogenated with NIS, NCS, and NBS under different reaction conditions. Chlorination and bromination were achieved with good yields by using acetonitrile as the solvent. However, iodination was only obtained in poor yields. Undoubtedly, the best conditions for both mono-and dihalogenation were the use of NBS, acetonitrile, and microwave assistance for short periods. 3,5-Dibromo-2-Aminopyrazine is an excellent functionalized starting material for the synthesis of nitrogen heterocycles.

Exploring the structural landscape of 2-aminopyrazines via co-crystallizations

A correlation between the electrostatic charge on the hydrogen-bond acceptor sites of 2-aminopyrazine derivatives and the ability of the compound to form intermolecular hydrogen bonds with carboxylic acids in the solid state has been established. The charge on the hydrogen-bond acceptor can be modulated which leads to a predictable lowering of the supramolecular yield of the reaction. The outcome of all reactions was screened using IR spectroscopy, and twelve new crystal structures are reported to verify the spectroscopic assignments, and to examine the exact nature of the primary intermolecular interactions. The binding preference of carboxylic acids towards the two possible binding sites of 2-aminopyrazines has also been examined, and the main driving force for the assembly of the heteromer between bases and carboxylic acids is the two-point O-H...N/O...H-N synthon. However, seven out of twelve times carboxylic acids also bind via a single-point O-H...N synthons. This 'synthon crossover' is unavoidable due to highly competitive binding sites present in the N-heterocyclic bases chosen.

Studies on pyrazines, 8. An improved synthesis of 2-amino-3,5-dibromo- and 2-amino-5-bromopyrazines

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