36070-75-4

Basic information

• Product Name: 2-CHLORO-5-CYANOPYRAZINE
• Synonyms: 2-CHLORO-5-CYANOPYRAZINE;5-CHLOROPYRAZINE-2-CARBONITRILE;5-Chloro-2-cyanopyrazine;C90110;2-Pyrazinecarbonitrile, 5-chloro-;EOS-61238
• CAS NO: 36070-75-4
• Molecular Formula: C₅H₂ClN₃
• Molecular Weight: 139.54
• Product Categories: Building Blocks;Pyrazine;carbonitrile
• Mol File: 36070-75-4.mol

Chemical Properties

• Melting Point: 44-45 ºC
• Boiling Point: 242 ºC
• Flash Point: 100 ºC
• Appearance: /
• Density: 1.43
• Vapor Pressure: 0.036mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -5.41±0.10(Predicted)
• CAS DataBase Reference: 2-CHLORO-5-CYANOPYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5-CYANOPYRAZINE(36070-75-4)
• EPA Substance Registry System: 2-CHLORO-5-CYANOPYRAZINE(36070-75-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• Hazardous Substances Data: 36070-75-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-5-cyanopyrazine is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of diverse chemical entities with potential medicinal applications.
Used in Agrochemical Production:
In the agrochemical industry, 2-Chloro-5-cyanopyrazine serves as a key intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its incorporation into these products helps enhance their effectiveness in controlling pests and weeds, thereby supporting agricultural productivity.
Used in Organic Compounds Synthesis:
2-Chloro-5-cyanopyrazine is also employed as an intermediate in the synthesis of organic compounds, which have a wide range of applications in various industries, such as chemical manufacturing, materials science, and specialty chemicals.
Used in Dyes and Pigments Production:
This chemical compound finds application in the production of dyes and pigments, where its unique properties contribute to the development of vibrant and stable colorants for various applications, including textiles, plastics, and inks.
Used in Material Science and Organic Chemistry Research:
Due to its distinctive chemical characteristics, 2-Chloro-5-cyanopyrazine holds potential for applications in the fields of material science and organic chemistry. It is primarily used in research and development, where scientists explore its properties and potential uses in creating new materials and chemical reactions.

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

Upstream product

• 768-36-5 2-pyrazinecarboxamide-4-oxide 
• 25594-31-4 3-pyrazinecarbonitrile N-oxide 
• 98-96-4 pyrazinamide 
• 21279-64-1 5-chloro-pyrazine-2-carboxylic acid amide 

Downstream Products

• 21279-64-1 5-chloro-pyrazine-2-carboxylic acid amide 
• 951657-84-4 1,4-bis-(2'-cyanopyrazin-5'-yl)phenylene 
• 1245079-30-4 [(3R,4S)-1-(5-cyanopyrazin-2-yl)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester 
• 1234015-66-7 tert-butyl (3-(2-(3-((5-cyanopyrazin-2-yl)amino)-1H-pyrazol-5-yl)-3-methoxyphenoxy)propyl)carbamate 

Relevant articles and documents

Benzoxaborole Antimalarial Agents. Part 4. Discovery of Potent 6-(2-(Alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles

A series of 6-hetaryloxy benzoxaborole compounds was designed and synthesized for a structure-activity relationship (SAR) investigation to assess the changes in antimalarial activity which result from 6-aryloxy structural variation, substituent modification on the pyrazine ring, and optimization of the side chain ester group. This SAR study discovered highly potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 27-34) with IC50s = 0.2-22 nM against cultured Plasmodium falciparum W2 and 3D7 strains. Compound 9 also demonstrated excellent in vivo efficacy against P. berghei in infected mice (ED90 = 7.0 mg/kg).

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 and antimycobacterial evaluation of N-substituted 3-aminopyrazine-2,5-dicarbonitriles

A series of 14 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and two types of Mycobacterium avium. The series comprised of N-substituted 3-aminopyrazine- 2,5-dicarbonitriles derived from 3-chloropyrazine-2,5- dicarbonitrile by nucleophilic substitution of chlorine by various non-aromatic amines (alkylamines, cycloalkylamines and heterocyclic amines). Noteworthy antimycobacterial activity against M. tuberculosis was found among the alkylamino derivatives, for example, 3-(heptylamino)pyrazine-2,5-dicarbonitrile inhibited M. tuberculosis at MIC = 51 lmol/L. 3-(Hexylamino)pyrazine-2,5- dicarbonitrile inhibited M. kansasii at MIC = 218 lmol/L. Basic structure-activity relationships are discussed. A comparison between calculated and experimentally determined lipophilicity parameters within the series is included.

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.