4,4'-Dihydroxyazobenzene

Base Information

• Chemical Name: 4,4'-Dihydroxyazobenzene
• CAS No.: 2050-16-0
• Molecular Formula: C12H10 N2 O2
• Molecular Weight: 214.224
• Hs Code.: 2927000090
• European Community (EC) Number: 622-644-7
• NSC Number: 402595
• UNII: F4YLC7I7DN
• Nikkaji Number: J7.865D
• Wikidata: Q27277636
• ChEMBL ID: CHEMBL116175
• Mol file: 2050-16-0.mol

Synonyms:4,4'-azobis(phenol);4,4'-dihydroxyazobenzene

Chemical Property of 4,4'-Dihydroxyazobenzene

Chemical Property:

• Melting Point: 204 °C
• Boiling Point: 392°Cat760mmHg
• PKA: 8.53±0.15(Predicted)
• Flash Point: 190.9°C
• PSA: 65.18000
• Density: 1.24g/cm³
• LogP: 3.51320
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 214.074227566
• Heavy Atom Count: 16
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,4''-Dihydroxyazobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N=NC2=CC=C(C=C2)O)O

Technology Process of 4,4'-Dihydroxyazobenzene

There total 40 articles about 4,4'-Dihydroxyazobenzene 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: 91.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 4,4'-dihydroxyazobenzene (2050-16-0)

Guidance literature:

4-nitro-phenol; In ethanol; for 0.0333333h;

With sodium tetrahydroborate; In ethanol; for 0.666667h; Reflux;

DOI:10.1039/c9ra01249d

Reference yield: 85.0%

4-amino-phenol (123-30-8) → 4,4'-dihydroxyazobenzene (2050-16-0)

Guidance literature:

With cetyl-trimethylammonium dichromate; In chloroform; for 3h; Heating;

DOI:10.1016/j.tetlet.2003.12.068

Reference yield: 70.1%

4-amino-phenol (123-30-8) + phenol (108-95-2,27073-41-2) → 4,4'-dihydroxyazobenzene (2050-16-0)

Guidance literature:

4-amino-phenol; With hydrogenchloride; sodium nitrite; In water; at 0 - 20 ℃;

phenol; With sodium hydroxide; In water; at 20 ℃; for 12h;

DOI:10.1002/adfm.202010114

upstream raw materials:

4-nitro-phenol

bis-(4-oxo-cyclohexa-2,5-dienylidene)-hydrazine

p-nitrosophenol

4-amino-phenol

Downstream raw materials:

2-chloro-4,4'-azo-di-phenol

4,4'-di-n-butoxyazoxybenzene

4,4'-di-n-heptyloxyazoxybenzene

bis-(4-octyloxy-phenyl)-diazene

Refernces

• 1、 Sun, Ruyi,Zhu, Liangliang. "Cyclodextrin-based ordered rotaxane-monolayers at gold surfaces". . p. 73527 - 73533. Retrieved 2016.
• 2、 Zhu, Liangliang,Yan, Hong,Nguyen, Kim Truc,Tian, He,Zhao, Yanli. "Sequential self-assembly for construction of Pt(ii)-bridged [3]rotaxanes on gold nanoparticles". . p. 4290 - 4292. Retrieved 2012.
• 3、 Wang, Jing,Jiang, Qian,Hao, Xingtian,Yan, Hongchao,Peng, Haiyan,Xiong, Bijin,Liao, Yonggui,Xie, Xiaolin. "Reversible photo-responsive gel-sol transitions of robust organogels based on an azobenzene-containing main-chain liquid crystalline polymer". . p. 3726 - 3733. Retrieved 2020.
• 4、 Sun, He-Lue,Chen, Yong,Zhao, Jin,Liu, Yu. "Photocontrolled Reversible Conversion of Nanotube and Nanoparticle Mediated by β-Cyclodextrin Dimers". . p. 9376 - 9380. Retrieved 2015.
• 5、 Chao, Danming,Zheng, Tian,Liu, Hongtao,Yang, Rui,Jia, Xiaoteng,Wang, Shutao,Berda, Erik B.,Wang, Ce. "A novel poly(aryl ether) containing azobenzene chromophore and pendant oligoaniline: Synthesis and electrochromic properties". . p. 253 - 258. Retrieved 2012.
• 6、 A?hoff, Sarah J.,Lancia, Federico,Iamsaard, Supitchaya,Matt, Benjamin,Kudernac, Tibor,Fletcher, Stephen P.,Katsonis, Nathalie. "High-Power Actuation from Molecular Photoswitches in Enantiomerically Paired Soft Springs". . p. 3261 - 3265. Retrieved 2017.
• 7、 Sahu, Satya Narayan,Rozhenko, Alexander B.,Eberhard, Jens,Mattay, Jochen. "Synthesis of a new photoresponsive molecular carcerand". . p. 165 - 174. Retrieved 2016.
• 8、 Arroyo Ma?ez, Pau,Biscussi, Brunella,Murray, Ana Paula,Richmond, Victoria,Sequeira, Maria Alejandra. "New photochromic azoderivatives with potent acetylcholinesterase inhibition". . . Retrieved 2021/06/12.
• 9、 Bao, Chunyan,Qu, Da-Hui,Tian, He,Wang, Chenxi,Wang, Shunkang,Wang, Xuebin,Xiang, Yanxin,Yang, Huiting,Zhu, Linyong. "A Light-Operated Molecular Cable Car for Gated Ion Transport". supporting information. p. 14836 - 14840. Retrieved 2021/05/10.