2050-14-8

Basic information

• Product Name: 2,2'-DIHYDROXYAZOBENZENE
• Synonyms: 2,2’-azobis-pheno;2,2'-DIHYDROXYAZOBENZENE;2,2'-AZODIPHENOL;1-(2-HYDROXYPHENYLAZO)-2-HYDROXYAZOBENZENE;DHAB;O,O'-DIHYDROXYAZOBENZENE;2,2'-azobisphenol;SpectrophotometricandfluorimetricreagentforAl,Mgandothermetals
• CAS NO: 2050-14-8
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• EINECS: 218-082-3
• Product Categories: Analytical Chemistry;Azo Compounds;Azobennzenes, etc. (Chelating Reagents);Chelating Reagents;Highly Purified Reagents;Other Categories;Refined Products by Sublimation
• Mol File: 2050-14-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 173-175 °C(lit.)
• Boiling Point: 354.35°C (rough estimate)
• Flash Point: 183.9°C
• Appearance: /
• Density: 1.2042 (rough estimate)
• Refractive Index: 1.6660 (estimate)
• PKA: 8.28±0.30(Predicted)
• CAS DataBase Reference: 2,2'-DIHYDROXYAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIHYDROXYAZOBENZENE(2050-14-8)
• EPA Substance Registry System: 2,2'-DIHYDROXYAZOBENZENE(2050-14-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 2050-14-8(Hazardous Substances Data)

Usage

Description

2,2'-Dihydroxyazobenzene is a small molecule that acts as an inhibitor of ADP ribosyl cyclase and is known to attenuate angiotensin (Ang) II-induced hypertrophic responses. It is formed during the oxidation of diclofenac by myeloperoxidase/hydrogen peroxide.

Uses

Used in Chemical Analysis:
2,2'-Dihydroxyazobenzene is used as a complexing reagent for the determination of aluminum in human serum by ion-pair reversed-phase partition HPLC. This application takes advantage of its ability to form complexes with specific elements, enabling accurate and efficient analysis in the field of chemical analysis.
Used in Pharmaceutical Research:
As an inhibitor of ADP ribosyl cyclase, 2,2'-dihydroxyazobenzene plays a role in pharmaceutical research, particularly in the study of enzymes and their functions. Its ability to attenuate certain hypertrophic responses makes it a valuable compound for investigating the underlying mechanisms of various diseases and conditions.
Used in Biochemical Processes:
The formation of 2,2'-dihydroxyazobenzene during the oxidation of diclofenac by myeloperoxidase/hydrogen peroxide highlights its involvement in biochemical processes. Understanding these processes can lead to the development of new therapeutic strategies and a better comprehension of how certain drugs interact with biological systems.

Upstream product

• 95-55-6 2-amino-phenol 
• 17396-91-7 sulfuric acid mono-(2-nitro-phenyl ester) 
• 7647-01-0 hydrogenchloride 
• 88-75-5 2-hydroxynitrobenzene 

Downstream Products

• 75205-45-7 1,2-azo-3,4,15,16-dibenzo-5,8,11,14-tetraoxacyclohexadecane 
• 223390-03-2 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-phenylazo}-phenoxy)-ethoxy]-ethanol 
• 855425-82-0 4,6,4'-trichloro-2,2'-azo-di-phenol 
• 858013-69-1 4,6,4',6'-tetrabromo-2,2'-azo-di-phenol 
• 95468-15-8 4-chloro-2,2'-azo-di-phenol 
• 88-89-1 2,4,6-Trinitrophenol 
• 95-55-6 2-amino-phenol 
• 223390-04-3 C₃₄H₃₈N₂O₁₀S₂ 
• 64-19-7 acetic acid 
• 78447-92-4 4,4'-dihydroxy-3,3'-azo-bis-benzenesulfonic acid 
• 876486-69-0 4,4'-dibromo-6,6'-dichloro-2,2'-azo-di-phenol 
• 858013-67-9 4,4'-diiodo-2,2'-azo-di-phenol 
• 856200-58-3 4-bromo-2,2'-azo-di-phenol 
• 855839-42-8 4-iodo-2,2'-azo-di-phenol 

Relevant articles and documents

Photochemical catalytic synthesis method of aromatic azo compound

The invention belongs to the field of photochemical organic synthesis, and particularly relates to a photochemical catalytic synthesis method of an aromatic azo compound, which comprises the followingstep: in the presence of light, a photocatalyst, a cocatalyst, a ligand, an alkali and a hydrogen donor, carrying out a deoxidation coupling reaction on a nitro-substituted aromatic compound to obtain the aromatic azo compound. According to the reaction system, the nitro-substituted aromatic compound can be selectively deoxidized and coupled to obtain the aromatic azo compound, and the highest yield of the product can reach 85% or above.

A Highly Efficient Near-Infrared-Emissive Copolymer with a N=N Double-Bond π-Conjugated System Based on a Fused Azobenzene–Boron Complex

Fused azobenzene–boron complexes (BAzs) show highly efficient near-infrared (NIR) emission from the nitrogen–nitrogen double bond (N=N) containing π-conjugated copolymer. Optical measurements showed that BAz worked as a strong electron acceptor because of the intrinsic electron deficiency of the N=N double bond and the boron–nitrogen (B?N) coordination which dramatically lowered the energy of the lowest unoccupied molecular orbital (LUMO) of the azobenzene ligand. The simple donor–acceptor (D–A) type copolymer of bithiophene (BT) and BAz exhibited intense photoluminescence (PL) in the NIR region both in the dilute solution (λPL=751 nm, ΦPL=0.25) and in the film (λPL=821 nm, ΦPL=0.038). The BAz monomer showed slight PL in the dilute solution, and aggregation-induced emission (AIE) was detected. We proposed that N=N double bonds should be attractive and functional building blocks for designing π-conjugated materials.

Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds

Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5 mol %) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.