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-]
• General Description: Benzofuroxan (Benzofurazan 1-oxide) is a reactive heterocyclic compound that participates in condensation reactions with 1,3-diketones to form quinoxaline derivatives, where its reactivity is influenced by the substituents on the diketone. Electron-donating groups favor the formation of 3-alkyl-2-aroylquinoxaline 1,4-dioxides, while electron-withdrawing groups or bulky substituents promote 2-alkanoyl-3-arylquinoxaline 1,4-dioxides. Additionally, heteroatom-containing substituents can lead to minor products via hydrogen bonding interactions.

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-methoxyphenazine

2,2-dimethyl-2H-benzimidazole 1,3-dioxide

2-phenyl-2-methyl-2H-benzimidazole-1,3-dioxide

2-(3-methoxybenzoyl)-3-methylquinoxaline 1,4-dioxide

Refernces

REACTION OF BENZOFURAZAN 1-OXIDE WITH 1-(2-NAPHTHYL)- AND 1-HETARYL-BUTANE-1,3-DIONES; PREPARATION OF ARYL AND HETARYL 2-QUINOXALINYL KETONES

10.1016/S0040-4020(01)89090-6

The research focuses on the synthesis of aryl and hetaryl 2-quinoxalinyl ketones through the reaction of benzofurazan 1-oxide (BFO) with 1-aryl- and 1-hetaryl-butane-1,3-diones, followed by reduction with sodium dithionite. The study explores the influence of the aryl or hetaryl group's structure in the 1,3-diketone on the reaction outcome with BFO. The researchers found that smaller alkyl groups and electron-donating aryl groups in the diketone favor the formation of 3-alkyl-2-aroylquinoxaline 1,4-dioxides, while larger alkyl groups and electron-withdrawing aryl groups favor the formation of 2-alkanoyl-3-arylquinoxaline 1,4-dioxides. Additionally, the presence of heteroatoms in the furyl or pyridyl substituents can lead to the formation of 2-acetyl-3-hetarylquinoxaline 1,4-dioxides as minor products due to hydrogen bonding.