6-Chloropyrazine-2-carbonyl chloride

Base Information

• Chemical Name: 6-Chloropyrazine-2-carbonyl chloride
• CAS No.: 148673-71-6
• Molecular Formula: C5H2 Cl2 N2 O
• Molecular Weight: 176.99
• DSSTox Substance ID: DTXSID70569093
• Nikkaji Number: J3.218.986E
• Wikidata: Q82455806
• Mol file: 148673-71-6.mol

Synonyms:6-chloropyrazine-2-carbonyl chloride;148673-71-6;Pyrazinecarbonyl chloride, 6-chloro- (9CI);2-Pyrazinecarbonyl chloride, 6-chloro-;SCHEMBL376231;DTXSID70569093;UHYKRNKLQNXGDA-UHFFFAOYSA-N;6-chloropyrazine-2-carbonylchloride;AKOS026730061;EN300-115068

Chemical Property of 6-Chloropyrazine-2-carbonyl chloride

Chemical Property:

• Boiling Point: 235.3±35.0 °C(Predicted)
• PKA: -3.87±0.10(Predicted)
• PSA: 42.85000
• Density: 1.549±0.06 g/cm3(Predicted)
• LogP: 1.50900
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 175.9544181
• Heavy Atom Count: 10
• Complexity: 142

Purity/Quality:

6-chloropyrazine-2-carbonylchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(N=C(C=N1)Cl)C(=O)Cl

Technology Process of 6-Chloropyrazine-2-carbonyl chloride

There total 6 articles about 6-Chloropyrazine-2-carbonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

6-chloropyrazine-2-carboxylic acid (23688-89-3) → 6-chloropyrazine-2-carboxylic acid chloride (148673-71-6)

Guidance literature:

With thionyl chloride; In benzene; for 1.5h; Heating;

DOI:10.1135/cccc19930452

Reference yield:

methyl pyrazine-2-carboxylate (6164-79-0) → 6-chloropyrazine-2-carboxylic acid chloride (148673-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 3-chloro-benzenecarboperoxoic acid / 1,2-dichloro-ethane / 16 h / 60 °C

2: thionyl chloride / 8 h / Reflux

3: ethanol; sodium hydroxide / 2 h / 20 °C

4: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 °C

With thionyl chloride; oxalyl dichloride; ethanol; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm201045m

Reference yield:

6-chloro-pyrazine-2-carboxylic acid methyl ester (23611-75-8) → 6-chloropyrazine-2-carboxylic acid chloride (148673-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol; sodium hydroxide / 2 h / 20 °C

2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 °C

With oxalyl dichloride; ethanol; sodium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm201045m

upstream raw materials:

6-chloropyrazine-2-carboxylic acid

methyl pyrazine-2-carboxylate

6-chloro-pyrazine-2-carboxylic acid methyl ester

methylester of pyrazinecarboxylic acid 4-oxide

Downstream raw materials:

(3aR,6aS)-tert-butyl 5-(6-(m-tolylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

(3aR,6aS)-tert-butyl 5-(6-(3-isopropoxyphenylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Refernces

• 1、 Dlabal, Karel,Dolezal, Martin,Machacek, Milos. "PREPARATION OF SOME 6-SUBSTITUTED N-PYRAZINYL-2-PYRAZINECARBOXAMIDES". . p. 452 - 454. Retrieved 1993.
• 2、 Dolezal, Martin,Palek, Lukas,Vinsova, Jarmila,Buchta, Vladimir,Jampilek, Josef,Kralova, Katarina. "Substituted pyrazinecarboxamides: Synthesis and biological evaluation". . p. 242 - 256. Retrieved 2006.
• 3、 Zitko, Jan,Jand'Ourek, Ond?ej,Paterová, Pavla,Navrátilová, Lucie,Kune?, Ji?í,Vin?ová, Jarmila,Dole?al, Martin. "Design, synthesis and antimycobacterial activity of hybrid molecules combining pyrazinamide with a 4-phenylthiazol-2-amine scaffold". . p. 685 - 696. Retrieved 2018.
• 4、 -. "SUBSTITUTED 2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONES AND USE OF SAME". Paragraph 0614-0615. . Retrieved 2020/12/13.
• 5、 Zitko, Jan,Barbora, Servusova-Vanaskova,Paterova, Pavla,Navratilova, Lucie,Trejtnar, Frantisek,Kunes, Jiri,Dolezal, Martin. "Design, synthesis and anti-mycobacterial evaluation of some new N-phenylpyrazine-2-carboxamides". . p. 649 - 657. Retrieved 2016/03/05.