5326-53-4

Basic information

• Product Name: 4,4''-Azobiphenyl
• Synonyms: 4,4''-Azobis(1,1'-biphenyl);4,4''-Azobisbiphenyl
• CAS NO: 5326-53-4
• Molecular Formula: C₂₄H₁₈N₂
• Molecular Weight: 334.41
• Mol File: 5326-53-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 528.2°C at 760 mmHg
• Flash Point: 266.4°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 1.03E-10mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 4,4''-Azobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4''-Azobiphenyl(5326-53-4)
• EPA Substance Registry System: 4,4''-Azobiphenyl(5326-53-4)

Safety Data

• Hazardous Substances Data: 5326-53-4(Hazardous Substances Data)

Usage

General Description

4,4''-Azobiphenyl, also known as azobenzene, is a chemical compound that consists of two benzene rings connected by an azo group (-N=N-). It is commonly used as a precursor in the synthesis of various organic compounds and as a building block for liquid crystals and dyes. Azobenzene is known for its ability to undergo reversible photoisomerization, where its molecular structure changes in response to light, making it a valuable component in the development of optoelectronic materials and molecular switches. Additionally, azobenzene has potential applications in the field of nanotechnology, particularly in the development of molecular-scale devices and systems. However, it is important to handle azobenzene with caution, as it is considered a hazardous chemical and has been classified as a possible human carcinogen.

InChI:InChI=1/C24H18N2/c1-3-7-19(8-4-1)21-11-15-23(16-12-21)25-26-24-17-13-22(14-18-24)20-9-5-2-6-10-20/h1-18H/b26-25+

Upstream product

• 92-93-3 1-phenyl-4-nitrobenzene 
• 6810-26-0 4-hydroxylaminobiphenyl 
• 495-48-7 azoxybenzene 
• 71-43-2 benzene 
• 7466-42-4 4-phenylazobenzene 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 17082-12-1 trans-azobenzene 
• 4088-58-8 4,4'-hydrazodibiphenyl 
• 7334-12-5 1,2-di([1,1'-biphenyl]-4-yl)diazene oxide 
• 60-29-7 diethyl ether 
• 95745-38-3 1,3-di([1,1'-biphenyl]-4-yl)urea 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 1601-97-4 bis-(4-iodo-phenyl)-diazene 

Downstream Products

• 92-67-1 4-phenylalanine 
• 92-69-3 4-Phenylphenol 
• 92-96-6 N,N'-bis-biphenyl-4-yl-thiourea 
• 17082-80-3 1.2.4.5-Tetrakis-biphenyl-4-yl-3.3.6.6-tetraphenyl-1.2.4.5-tetraaza-3.6-disila-cyclohexan 

Relevant articles and documents

Ruthenium porphyrins with axial π-conjugated arylamide and arylimide ligands

A series of ruthenium porphyrins [RuIV(por)(NHY)2] and [RuVI(por)(NY)2] bearing axially coordinated π-conjugated arylamide and arylimide ligands, respectively, have been synthesized. The crystal structures of [RuIV(tmp)(NHY)2] (tmp=5,10,15,20-tetramesitylporphyrinato(2-)) with Y=4-methoxy-biphenyl-4-yl (Ar-Ar-p-OMe), 4-chloro-biphenyl-4-yl (Ar-Ar-p-Cl), and 9,9-dibutyl-fluoren-2-yl (Ar^Ar) show axial Ru-N(arylamide) distances of 1.978(4), 1.971(6), and 1.985(13) A, respectively. [RuIV(tmp)(NH{Ar^Ar})2] is an example of metalloporphyrins that bind an arylamide ligand featuring a co-planar biphenyl unit. The [RuIV(por)(NHY)2] complexes show a quasi-reversible reduction couple or irreversible reduction wave attributed to RuIV→RuIII with Epc from -1.06 to -1.40 V versus Cp2Fe+/0 and an irreversible oxidation wave with Epa from -0.04 to 0.19 V versus Cp 2Fe+/0. Reaction of the [RuIV(por)(NHY) 2] with bromine afforded [RuIV(por)(NHY)Br]. PhI(OAc) 2 oxidation of the [RuIV(por)(NHY)2] gave [RuVI(por)(NY)2]; the latter can be prepared from reaction of [RuII(por)(CO)] with aryl azides N3Y. The crystal structure of [RuVI(tmp)(N{Ar-Ar-p-OMe})2] features Ru-N(arylimide) distances of 1.824(5) and 1.829(5) A. Alkene aziridination and C-H amination catalyzed by [RuII(tmp)(CO)]+π-conjugated aryl azides , or mediated by [RuVI(por)(NY)2] with Y=biphenyl-4-yl (Ar-Ar) and Ar-Ar-p-Cl, gave aziridines and amines in moderate yields. The electronic structure of [RuVI(por)(NY)2] was examined by DFT calculations.

Ruthenium nanoparticle-catalyzed, controlled and chemoselective hydrogenation of nitroarenes using ethanol as a hydrogen source

This communication describes a ruthenium nanoparticle-catalyzed reduction of nitroarenes giving azoxyarenes, azoarenes, or anilines in good to excellent yields using ethanol as a hydrogen source. Copyright

Facile synthesis of azo compounds from aromatic nitro compounds using magnesium and triethylammonium formate

Magnesium/triethylammonium formate is a convenient reagent for the reduction of aromatic nitro compounds to corresponding symmetrically substituted azo compounds. Various azo compounds containing additional reducible substituents, including halogen, nitrile, acid, phenol, ester, and methoxy functions, have been synthesized in a single step by the use of this reagent. The conversion is reasonably fast, clean, high yielding, and occurs at room temperature in methanol.