6863-74-7

Basic information

• Product Name: 6-chloropyrazine-2-carbonitrile
• Synonyms: 6-chloropyrazine-2-carbonitrile;2-Chloro-6-cyanopyrazine;6-Chloro-2-pyrazinecarbonitrile;6-Cyano-2-chloropyrazine;6-Chloropyrazinecarbonitrile;Pyrazinecarbonitrile, 6-chloro-;2-Chloro-6-pyrazinecarbonitrile;2-Cyano-6-chloropyrazine
• CAS NO: 6863-74-7
• Molecular Formula: C₅H₂ClN₃
• Molecular Weight: 139.54
• Product Categories: Building Blocks;Pyrazine
• Mol File: 6863-74-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 24-26℃
• Boiling Point: 229℃
• Flash Point: 93℃
• Appearance: /
• Density: 1.43
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.99±0.10(Predicted)
• CAS DataBase Reference: 6-chloropyrazine-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloropyrazine-2-carbonitrile(6863-74-7)
• EPA Substance Registry System: 6-chloropyrazine-2-carbonitrile(6863-74-7)

Safety Data

• Hazardous Substances Data: 6863-74-7(Hazardous Substances Data)

Usage

General Description

6-Chloropyrazine-2-carbonitrile is a chemical compound with the formula C5H2ClN3. It is a chlorinated pyrazine derivative, and it is commonly used in the synthesis of various pharmaceutical and agrochemical products. 6-chloropyrazine-2-carbonitrile is a white to off-white solid that is sparingly soluble in water but soluble in organic solvents. It is also known to be a potential intermediate in the manufacturing of various drugs and agricultural chemicals. Additionally, 6-chloropyrazine-2-carbonitrile has been studied for its potential biological activities, including as an anticancer and antibacterial agent. However, it is important to handle this chemical with care, as it may pose hazards to human health and the environment.

InChI:InChI=1/C5H2ClN3/c6-5-3-8-2-4(1-7)9-5/h2-3H

Upstream product

• 98-96-4 pyrazinamide 
• 32046-03-0 2-Cyanopyrazine 1-Oxide 
• 25594-31-4 3-pyrazinecarbonitrile N-oxide 
• 768-36-5 2-pyrazinecarboxamide-4-oxide 

Downstream Products

• 664308-20-7 4-(4-cyanophenyl)-3,4,5,6-tetrahydro-2H-[1,2']-bipyrazinyl-6'-carbonitrile 
• 1431319-98-0 6-chloro-N'-(2-chlorophenylsulfonyl)pyrazine-2-carboximidamide 
• 1445800-13-4 6-(3-(1-(2-(benzothiazol-2-yl)hydrazono)ethyl)phenyl)pyrazine-2-carboxylic acid 
• 1445800-12-3 6-(3-acetylphenyl)pyrazine-2-carboxylic acid 
• 1454659-02-9 6-(3-acetylphenyl)pyrazine-2-carboxylic acid 
• 1418269-68-7 C₁₄H₁₁N₅ 
• 1418269-67-6 C₁₄H₈F₃N₅ 
• 1418269-66-5 C₁₃H₈N₆O₂ 
• 1418269-65-4 C₁₃H₇Cl₂N₅ 
• 1418269-63-2 C₁₃H₈ClN₅ 
• 1418269-62-1 C₁₃H₁₀N₆ 
• 1418269-61-0 C₁₄H₁₁N₅O 
• 1418269-60-9 C₁₄H₁₁N₅ 
• 1418269-59-6 C₁₃H₉N₅ 

Relevant articles and documents

Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution

A series of 19 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro whole cell antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two types of Mycobacterium avium. The series consisted of 3-(benzylamino)-5-cyanopyrazine-2-carboxamides and 3-(benzylamino)pyrazine-2,5-dicarbonitriles with various substituents on the phenyl ring. RP-HPLC method was used to determine the lipophilicity of the prepared compounds. Nine compounds exerted similar or better activity against Mycobacterium tuberculosis compared to pyrazinamide (MIC = 6.25-12.5 μg/mL). 3-(Benzylamino)pyrazine-2,5-dicarbonitrile inhibited all of the tested mycobacterial strains with MIC within the range 12.5-25 μg/mL. Although not the most active, 4-NH2 substituted compounds possessed the lowest in vitro cytotoxicity (hepatotoxicity), leading to selectivity index SI = 5.5 and SI >21.

Synthesis, antimycobacterial and antifungal evaluation of 3-arylaminopyrazine-2,5-dicarbonitriles

This paper describes preparation and biological evaluation of pyrazinamide analogues. Pyrazinamide with its simple structure gives a good opportunity for further modification regarding an increase of its antimycobacterial activity. We prepared a series of compounds derived from pyrazine-2,5-dicarbonitrile with arylamino substitution in position 3. All compounds were assayed in vitro against major Mycobacterium and various Fungi species. The best activity was found in 3-{[3-(trifluoromethyl)phenyl]amino}pyrazine-2,5-dicarbonitrile 11 with the value of 6.25 μmol-1 against M. tuberculosis H37Rv and moderate activity against minor Mycobacterium pathogens.