5-(2-Nitrophenyl)-4H-1,2,4-triazole-3-thiol

Base Information

• Chemical Name: 5-(2-Nitrophenyl)-4H-1,2,4-triazole-3-thiol
• CAS No.: 6219-49-4
• Molecular Formula: C₈H₆N₄O₂S
• Molecular Weight: 222.227
• DSSTox Substance ID: DTXSID901260046
• Nikkaji Number: J2.995.534D
• Mol file: 6219-49-4.mol

Synonyms:3-(2-nitrophenyl)-1H-1,2,4-triazole-5(4H)-thione

Chemical Property of 5-(2-Nitrophenyl)-4H-1,2,4-triazole-3-thiol

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 222.02114662
• Heavy Atom Count: 15
• Complexity: 325

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C2=NC(=S)NN2)[N+](=O)[O-]

Technology Process of 5-(2-Nitrophenyl)-4H-1,2,4-triazole-3-thiol

There total 9 articles about 5-(2-Nitrophenyl)-4H-1,2,4-triazole-3-thiol 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: 85.0%

N2-(2-nitrobenzoyl)thiosemicarbazide (835-14-3) → 3-(o-nitrophenyl)-5-mercapto-4H-1,2,4-triazole (6219-49-4)

Guidance literature:

With sodium hydroxide; for 3h;

DOI:10.1002/jhet.1600

Reference yield:

N2-(2-nitrobenzoyl)thiosemicarbazide (835-14-3) → 5-(2-nitro-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione (6219-49-4)

Guidance literature:

With sodium hydroxide; In water; at 100 ℃; for 3h;

DOI:10.1016/j.bioorg.2020.104078

Reference yield:

thiosemicarbazide (79-19-6) + 2-nitrobenzyl chloride (610-14-0) → 3-(o-nitrophenyl)-5-mercapto-4H-1,2,4-triazole (6219-49-4) + 5-(2-nitro-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione (6219-49-4)

Guidance literature:

thiosemicarbazide; 2-nitrobenzyl chloride; With pyridine; at 20 ℃; for 16h;

With water; sodium hydroxide; at 100 ℃; for 3h; Further stages;

upstream raw materials:

N₂-(2-nitrobenzoyl)thiosemicarbazide

2-nitrobenzyl chloride

ortho-nitrobenzoic acid

thiosemicarbazide

Downstream raw materials:

4-(2-{[5-(2-nitrophenyl)-4H-1,2,4-triazol-3-yl]thio}ethoxy)benzaldehyde

Refernces

• 1、 Xiao, Shengnan,Wang, Xude,Xu, Lei,Li, Tao,Cao, Jiaqing,Zhao, Yuqing. "Novel panaxadiol triazole derivatives induce apoptosis in HepG-2 cells through the mitochondrial pathway". . . Retrieved 2020/07/23.
• 2、 Mohammed Iqbal,Khan, Ashraf Y.,Kalashetti, Mallikarjun B.,Belavagi, Ningaraddi S.,Gong, Young-Dae,Khazi, Imitiyaz Ahmed M.. "Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring". body text. p. 308 - 315. Retrieved 2012/08/08.