Azoxybenzene

Base Information

• Chemical Name: Azoxybenzene
• CAS No.: 495-48-7
• Deprecated CAS: 55599-32-1
• Molecular Formula: C12H10 N2 O
• Molecular Weight: 198.224
• Hs Code.: 29153100
• European Community (EC) Number: 207-802-1
• NSC Number: 1796
• UNII: DC1P3JE72O,2CYQ7PT9SS
• Wikidata: Q5715108,Q27122876,Q27122880
• Metabolomics Workbench ID: 57935
• ChEMBL ID: CHEMBL1442921,CHEMBL2356614
• Mol file: 495-48-7.mol

Synonyms:azoxybenzene;fenazox;fenazox, (E)-isomer;fenazox, (Z)-isomer

Chemical Property of Azoxybenzene

Chemical Property:

• Appearance/Colour: ORANGE-YELLOW TO ORANGE CRYSTALS
• Melting Point: 32-36 °C
• Refractive Index: 1.582
• Boiling Point: 130 °C / 0.9mmHg
• Flash Point: 157°C
• PSA: 41.11000
• Density: 1.09g/cm³
• LogP: 4.13550
• Storage Temp.: 0-6°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 198.079312947
• Heavy Atom Count: 15
• Complexity: 216

Purity/Quality:

98%, ^*data from raw suppliers

Fenazox ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/22
• Safety Statements: 28A-28

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)N=[N+](C2=CC=CC=C2)[O-]
• Uses: Fenazox is used in the synthetic preparation of amides via reductive amidation of esters, which is used in the synthesis of bio-active molecules and natural products.

Technology Process of Azoxybenzene

There total 715 articles about Azoxybenzene 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%

nitrobenzene (98-95-3,26969-40-4) → azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With ammonium chloride; zinc; In water; at 80 ℃; for 24h; Concentration; Temperature; Time; Catalytic behavior; Inert atmosphere;

Reference yield: 97.0%

N-Phenylhydroxylamine (100-65-2) → azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With dihydrogen peroxide; 34>(3-); In chloroform; for 2h; Ambient temperature;

DOI:10.1021/jo00066a012

Reference yield: 90.0%

nitrobenzene (98-95-3,26969-40-4) → aniline (62-53-3) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane; In toluene; at 60 ℃; for 4h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1055/s-0034-1378850

upstream raw materials:

pyridine

sodium methylate

nitrobenzene

ethanol

Downstream raw materials:

trans-azoxybenzene

2-phenylazo-phenol

N-(4-chlorophenyl)acetamide

bis-(4-chloro-phenyl)-diazene

Refernces

• 1、 Naveenkumar, Akula,Kuruva, Praveena,Shivakumara, Chikkadasappa,Srilakshmi, Chilukoti. "Mixture of fuels approach for the synthesis of SrFeO3-δ nanocatalyst and its impact on the catalytic reduction of nitrobenzene". . p. 12178 - 12185. Retrieved 2014.
• 2、 Rorta, F.,Pizzotti, M.,Cenini, S.. "THE CATALYTIC TRANSFORMATION OF NITROSOBENZENE INTO AZOXY AND AZOBENZENE". . p. 279 - 284. Retrieved 1981.
• 3、 Oae et al.. "-". . p. 728. Retrieved 1963.
• 4、 Kagami,Motoki. "-". . p. 1267. Retrieved 1978.
• 5、 Piepgrass, Kent,Pope, Michael T.. "Oxygen Atom Transfer Chemistry of Heteropolytungstane "Browns" in Nonaqueous Solvents". . p. 753 - 754. Retrieved 1989.
• 6、 Dovganyuk, V. F.,Sharf, V. Z.,Belyaeva, V. K.,Marov, I. N.,Dykh, Zh. L.,et al.. "STRUCTURE AND CATALYTIC ACTIVITY OF METAL COMPLEXES ON CARRIERS. 3. RHODIUM COMPLEXES ON MODIFIED POLYMERS AND THEIR CATALYTIC PROPERTIES IN THE REDUCTION OF NITROBENZENE BY CHEMICALLY BOUND HYDROGEN". . p. 217 - 221. Retrieved 1990.
• 7、 Long, Yu,Luo, Nan,Ma, Jiantai,Qin, Jiaheng,Sun, Fangkun,Wang, Wei David,Zhou, Pan-Pan. "Zr(OH)4-Catalyzed Controllable Selective Oxidation of Anilines to Azoxybenzenes, Azobenzenes and Nitrosobenzenes". supporting information. . Retrieved 2021/12/09.
• 8、 Zhou, Xueke,Zhao, Haitao,Liu, Shaojun,Yang, Yang,Qu, Ruiyang,Zhen, Chenghang,Gao, Xiang. "The relationship of morphology and catalytic performance of CeO2 catalysts for reducing nitrobenzene to azoxybenzene under the base-free condition". supporting information. p. 761 - 764. Retrieved 2020/07/17.