Benzofurazan, 4-nitro-7-(phenylthio)-

Base Information

• Chemical Name: Benzofurazan, 4-nitro-7-(phenylthio)-
• CAS No.: 16322-23-9
• Molecular Formula: C12H7 N3 O3 S
• Molecular Weight: 273.272
• NSC Number: 228145
• UNII: MLW3MG733L
• DSSTox Substance ID: DTXSID30167539
• Wikidata: Q83036931
• Pharos Ligand ID: PC99AVDAY43Z
• ChEMBL ID: CHEMBL2430537
• Mol file: 16322-23-9.mol

Synonyms:7-nitro-4-(phenylthio)benzofurazan;NBF-SPh

Chemical Property of Benzofurazan, 4-nitro-7-(phenylthio)-

Chemical Property:

• Vapor Pressure: 9.03E-09mmHg at 25°C
• Boiling Point: 476.1°C at 760 mmHg
• Flash Point: 241.7°C
• Density: 1.53g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 273.02081227
• Heavy Atom Count: 19
• Complexity: 333

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SC2=CC=C(C3=NON=C23)[N+](=O)[O-]

Technology Process of Benzofurazan, 4-nitro-7-(phenylthio)-

There total 8 articles about Benzofurazan, 4-nitro-7-(phenylthio)- 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: 82.0%

thiophenol (108-98-5) + NBD chloride (10199-89-0) → 4-nitro-7-(phenylthio)benzo[c][1,2,5]oxadiazole (16322-23-9)

Guidance literature:

In ethanol; for 0.416667h; Reflux; Alkaline conditions;

DOI:10.1016/j.bmcl.2013.08.048

Reference yield: 76.0%

4-Fluorothiophenol (371-42-6) + NBD chloride (10199-89-0) → 4-nitro-7-(phenylthio)benzo[c][1,2,5]oxadiazole (16322-23-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jo4008095

Reference yield:

5-chlorobenzofurazan-1-oxide (17348-69-5) → 4-nitro-7-(phenylthio)benzo[c][1,2,5]oxadiazole (16322-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) NH₂OH*HCl, EtOH, H₂O, (ii) KOH

2: HNO₃, H₂SO₄

3: Py / ethanol

With pyridine; sulfuric acid; nitric acid; In ethanol;

DOI:10.1021/jm00308a027

upstream raw materials:

thiophenol

5-chloro-4-nitrobenzo[c]-[1,2,5]oxadiazole

NBD chloride

4-bromo-7-nitro-2,1,3-benzoxadiazole

Downstream raw materials:

7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol

thiophenol

4-Phenylsulphinyl-7-nitrobenzofurazan

4-nitro-7-(phenylsulfonyl)benzo[c][1,2,5]oxadiazole

Refernces

• 1、 Li, Dongyang,Chen, Weijie,Liu, Sheng Hua,Chen, Xiaoqiang,Yin, Jun. "The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1,2,5]oxadiazole dyes". supporting information. p. 2891 - 2896. Retrieved 2020/03/19.
• 2、 Kessler, Ulrich,Castagnolo, Daniele,Pagano, Mafalda,Deodato, Davide,Bernardini, Martina,Pilger, Beatrice,Ranadheera, Charlene,Botta, Maurizio. "Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus". supporting information. p. 5575 - 5577. Retrieved 2013/10/01.