Benzofuroxan

Base Information

• Chemical Name: Benzofuroxan
• CAS No.: 480-96-6
• Molecular Formula: C6H4N2O2
• Molecular Weight: 136.11
• Hs Code.: 29322090
• European Community (EC) Number: 207-559-1
• NSC Number: 19930
• UNII: 34FFO6Y520
• Nikkaji Number: J12.992E
• Wikidata: Q63398345
• ChEMBL ID: CHEMBL2413971
• Mol file: 480-96-6.mol

Synonyms:benzo-2-oxa-1,3-diazole-N-oxide;benzofuroxan

Chemical Property of Benzofuroxan

Chemical Property:

• Appearance/Colour: mustard colored powder
• Vapor Pressure: 0.0433mmHg at 25°C
• Melting Point: 66-69 °C
• Refractive Index: 1.676
• Boiling Point: 246.2 °C at 760 mmHg
• PKA: 4.58±0.46(Predicted)
• Flash Point: 102.7 °C
• PSA: 51.49000
• Density: 1.49 g/cm³
• LogP: 1.25630
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 136.027277375
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

99%, ^*data from raw suppliers

Benzofuroxan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NO[N+](=C2C=C1)[O-]
• Uses: Benzofuroxan is used as an oxidant for the preparation of 2-arylsubstituted benzimidazoles, quinoxalines and 1,4-bis(alkylamino)-9,10-anthracenediones. It is also sued in the synthesis of 1,2-dinitrosobenzene.

Technology Process of Benzofuroxan

There total 33 articles about Benzofuroxan 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: 100.0%

o-dinitrosobenzene (7617-57-4) → benzofurazan oxide (480-96-6,68100-26-5)

Guidance literature:

at -203.1 ℃;

DOI:10.1021/jo00017a042

Reference yield: 97.0%

2-nitro-aniline (88-74-4) → benzofurazan oxide (480-96-6,68100-26-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In acetone; at 30 ℃; for 17h;

DOI:10.1071/CH9920371

Reference yield: 95.0%

N-benzoyloxy-2-nitrobenzenamine (127526-86-7) → benzofurazan oxide (480-96-6,68100-26-5) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 25.05 ℃; Further Variations:; Reagents; Solvents; Temperatures; Kinetics; Product distribution;

DOI:10.1071/CH01110

upstream raw materials:

o-benzoquinone-1,2-dioxime

o-azidonitrobenzene

[bis(acetoxy)iodo]benzene

2-nitro-aniline

Downstream raw materials:

2-nitro-aniline

quinoxaline 1,4-di-N-oxide

1,2-diamino-benzene

4,6-dinitrobenzofuroxan

Refernces

• 1、 Lipilin,Karslyan,Churakov,Strelenko,Tartakovsky. "Intramolecular interaction between ortho-azido and azoxy groups as a new way of forming a N-N bond. Synthesis of 2-alkylbenzotriazole 1-oxides". . p. 1013 - 1020. Retrieved 2005.
• 2、 Dunkin,Lynch,Boulton,Henderson. "1,2-dinitrosobenzene in argon matrices at 14 K". . p. 1178 - 1179. Retrieved 1991.
• 3、 Dyall, Leonard K.. "Mass Spectral Fragmentation of Benzofurazan-1-oxide". . p. 519 - 522. Retrieved 1987.
• 4、 Huang, Lingli,Lu, Qirong,Pan, Yuanhu,Qu, Wei,Xie, Shuyu,Yuan, Zonghui,Zhang, Heying,Zhang, Jie. "Discovery of novel nitrogenous heterocyclic-containing quinoxaline-1,4-di-N-oxides as potent activator of autophagy in M.tb-infected macrophages". . . Retrieved 2021/07/06.
• 5、 -. "Preparation method of mequindox". Paragraph 0046-0063. . Retrieved 2019/02/08.