5320-91-2

Basic information

• Product Name: AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER
• Synonyms: Azobenzene-4,4'-dicarboxylic Acid Dimethyl Ester 4,4'-Azodibenzoic Acid Dimethyl Ester Dimethyl 4,4'-Azodibenzoate;Dimethyl 4,4'-(diazene-1,2-diyl);DIMETHYL AZOBENZENE-4,4'-DICARBOXYLATE;DIMETHYL 4,4'-AZODIBENZOATE;AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER;4,4'-AZODIBENZOIC ACID DIMETHYL ESTER;methyl 4-[(4-methoxycarbonylphenyl)diazenyl]benzoate
• CAS NO: 5320-91-2
• Molecular Formula: C₁₆H₁₄N₂O₄
• Molecular Weight: 298.29
• Product Categories: Aromatic Esters
• Mol File: 5320-91-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 240 °C
• Boiling Point: 450.676ºC at 760 mmHg
• Flash Point: 198.956ºC
• Appearance: /
• Density: 1.201g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER(5320-91-2)
• EPA Substance Registry System: AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER(5320-91-2)

Safety Data

• Hazardous Substances Data: 5320-91-2(Hazardous Substances Data)

Usage

General Description

AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER is a chemical compound commonly used in the synthesis of liquid crystal materials and dyes. It consists of a benzene ring with two carboxylic acid groups and two ester groups attached. AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER has the ability to undergo photoisomerization, which makes it suitable for use in the manufacture of light-sensitive materials and photomechanical processes. Additionally, it is also used in the production of polymers and as a building block for the synthesis of more complex organic compounds. Overall, AZOBENZENE-4,4'-DICARBOXYLIC ACID DIMETHYL ESTER has a wide range of applications in the fields of chemistry, materials science, and photochemistry.

InChI:InChI=1/C16H14N2O4/c1-21-15(19)11-3-7-13(8-4-11)17-18-14-9-5-12(6-10-14)16(20)22-2/h3-10H,1-2H3

Upstream product

• 619-45-4 4-methoxycarbonyl aniline 
• 67-56-1 methanol 
• 10252-29-6 azobenzene-4,4'-dicarbonyl dichloride 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 108-24-7 acetic anhydride 
• 582-69-4 azoxybenzene-4,4'-dicarboxylic acid 
• 20442-96-0 methyl 4-azidobenzoate 
• 103-71-9 phenyl isocyanate 
• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 99-27-4 dimethyl 5-aminoisophthalate 
• 1227297-30-4 dimethyl hydrazobenzene-4,4'-dicarboxylate 
• 2491-52-3 4-nitroazobenzene 
• 122045-07-2 4,4'-(diazene-1,2-diyl)dibenzonitrile 

Downstream Products

• 164596-20-7 4-tert-butoxycarbonylamino-benzoic acid methyl ester 
• 586-91-4 azobenzene-4,4'-dicarboxylic acid 
• 37797-30-1 4,4’-bis(hydroxymethyl)azobenzene 
• 1227297-30-4 dimethyl hydrazobenzene-4,4'-dicarboxylate 
• 2491-52-3 4-nitroazobenzene 
• 122045-07-2 4,4'-(diazene-1,2-diyl)dibenzonitrile 

Relevant articles and documents

Supramolecular detection of geometrical differences of azobenzene carboxylates

In dynamic combinatorial chemistry, the geometry of a template can be translated into the composition of a library of interchanging components. In this study, such a dynamic combinatorial library was used for the first time to detect and evaluate differences in the geometry of isomers of photoswitchable azobenzene based templates.

Au@zirconium-phosphonate nanoparticles as an effective catalytic system for the chemoselective and switchable reduction of nitroarenes

In the present paper, a novel inorganic-organic layered material, a zirconium phosphate aminoethyl phosphonate, ZP(AEP), bearing aminoethyl groups on the layer surface, was used to immobilize AuNPs by a two-step procedure. The gold-based catalyst, Au1@ZP(AEP), containing 1 wt% Au, was characterized in terms of physico-chemical properties and TEM analysis revealed that the AuNPs have a spherical shape and an average size of 7.8 (±2.4) nm. Au1@ZP(AEP) proved its high efficiency for the chemoselective reduction of nitroarenes under mild conditions. Both batch and flow condition protocols have been defined. The catalytic system has been proven to be able to easily switch chemoselectivity allowing the control of the reduction of a series of nitroaromatics towards their corresponding azoxyarenes (2a-k) or anilines (2a-l) in 96% EtOH or abs EtOH, respectively, by using NaBH4 as a reducing agent, in good to excellent yields. Recovery and reuse of the catalytic system has been investigated proving the benefits of the flow approach.

Catalytic Azoarene Synthesis from Aryl Azides Enabled by a Dinuclear Ni Complex

Azoarenes are valuable chromophores that have been extensively incorporated as photoswitchable elements in molecular machines and biologically active compounds. Here, we report a catalytic nitrene dimerization reaction that provides access to structurally and electronically diverse azoarenes. The reaction utilizes aryl azides as nitrene precursors and generates only gaseous N2 as a byproduct. By circumventing the use of a stoichiometric redox reagent, a broad range of organic functional groups are tolerated, and common byproducts of current methods are avoided. A catalyst featuring a Ni - Ni bond is found to be uniquely effective relative to those containing only a single Ni center. The mechanistic origins of this nuclearity effect are described.