Azoxybenzene

Base Information

• Chemical Name: Azoxybenzene
• CAS No.: 20972-43-4
• Deprecated CAS: 55599-32-1
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.224
• 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: 20972-43-4.mol

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

Chemical Property of Azoxybenzene

Chemical Property:

• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)N=[N+](C2=CC=CC=C2)[O-]

Technology Process of Azoxybenzene

There total 172 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: 79.0%

furfural (98-01-1) + methanol (67-56-1) → 2-furoic acid methyl ester (611-13-2) + trans-azobenzene (17082-12-1) + trans-azoxybenzene (20972-43-4,21650-65-7,495-48-7,55599-32-1)

Guidance literature:

With nitrobenzene; triethylamine; N-methyl-4,5-dimethylthiazolium iodide; at 60 ℃; for 96h; Heating;

DOI:10.1016/0040-4020(82)80170-1

Reference yield: 59.0%

methanol (67-56-1) + benzaldehyde (100-52-7) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + aniline (62-53-3) + trans-azoxybenzene (20972-43-4,21650-65-7,495-48-7,55599-32-1)

Guidance literature:

With nitrobenzene; triethylamine; N-methyl-4,5-dimethylthiazolium iodide; at 65 ℃; for 264h;

DOI:10.1016/0040-4020(82)80170-1

Reference yield: 51.0%

Nitrosobenzene (586-96-9) → aniline (62-53-3) + Azobenzene (1227476-15-4) + trans-azoxybenzene (20972-43-4,21650-65-7,495-48-7,55599-32-1)

Guidance literature:

With carbon monoxide; oxygen; palladium dichloride; In methanol; for 18h; under 760 Torr; Product distribution; Ambient temperature;

DOI:10.1016/S0040-4039(00)96874-6

upstream raw materials:

1,4-dioxane

1-methyl-4-nitrosobenzene

N-Phenylhydroxylamine

Nitrosobenzene

Downstream raw materials:

Azobenzene

trans-azoxybenzene

2-phenylazo-phenol

N-(4-chlorophenyl)acetamide

Refernces

• 1、 Srivastava,Khan,Nicholas. "A novel intermediate in allylic amination catalyzed by iron salts". . p. 3311 - 3312. Retrieved 1996.
• 2、 Blackie, Josie A.,Turner, Nicholas J.,Wells, Andrew S.. "Concerning the baker's yeast (Saccharomyces cerevisiae) mediated reduction of nitroarenes and other N-O containing functional groups". . p. 3043 - 3046. Retrieved 1997.
• 3、 Yano, Yumihiko,Sakaguchi, Terukiyo,Nakazato, Michiaki. "MARKED METAL ION EFFECTS IN ELECTRON TRANSFER FROM REDUCED FLAVIN TO AROMATIC NITRO COMPOUNDS IN ETHANOL". . p. 595 - 600. Retrieved 1984.
• 4、 Liu, Yuxuan,Miao, Wang,Tang, Weijun,Xue, Dong,Xiao, Jianliang,Wang, Chao,Li, Changzhi. "Rhodium-terpyridine Catalyzed Transfer Hydrogenation of Aromatic Nitro Compounds in Water". supporting information. p. 1725 - 1729. Retrieved 2021/06/01.
• 5、 Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen. "NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes". supporting information. p. 5349 - 5353. Retrieved 2021/07/21.