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

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 24241-18-7 differently. You can refer to the following data:
1. 2-Amino-3,5-dibromopyrazine is used in the preparation of conjugated polymers for neurotoxin detection. 2-Amino-3,5-dibromopyrazine is an intermediate in the preparation of rho kinase (ROCK) inhibitor s.
2. 2-Amino-3,5-dibromopyrazine may be used in the synthesis of:2-amino-5-bromopyrazin-3-thiol2-amino-3,5-bis(p-methoxyphenyl)-1,4-pyrazine3,7-dihydroimidazo[1,2a]pyrazine-3-ones

General Description

2-Amino-3,5-dibromopyrazine can be synthesized from 2-aminopyrazine via bromination using N-bromosuccinimide (NBS). It reacts with sodium dicyanocuprate to form a mixture of mono and dicyanation products. The formation of 2-aminothiazolopyrazines by reacting 2-amino-3,5-dibromopyrazine with isothiocyanates has been reported.

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

• 87597-21-5 ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate 
• 639450-08-1 5-bromo-N₃-(2-methoxybenzyl)-pyrazine-2,3-diamine 
• 767343-16-8 (S)-6-bromo-N₂-(1-phenylethyl)pyrazine-2,3-diamine 
• 827602-49-3 4-[(3-amino-6-bromo-pyrazin-2-ylamino)-methyl]-phenol 
• 875781-41-2 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine 
• 894807-97-7 5-bromo-3-(4-methyl-1,4-diazepan-1-yl)-pyrazin-2-amine 
• 648891-10-5 2,6-dibromo-3-(4-methylphenylsulfonylamino)pyrazine 
• 1219956-75-8 5-bromo-N³-(2,6-dichlorobenzyl)pyrazine-2,3-diamine 
• 1219956-60-1 C₁₁H₉BrClN₃O 
• 756503-75-0 5-bromo-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyrazin-2-ylamine 
• 1005490-99-2 6-bromo-N2-(pentan-3-yl)pyrazine-2,3-diamine 
• 1021918-23-9 (R)-6-bromo-N₂-(1-phenylethyl)pyrazine-2,3-diamine 

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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