1545-85-3

Upstream product

• 1545-83-1 4-fluoroazobenzene 
• 371-40-4 4-fluoroaniline 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 326-04-5 N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide 

Downstream Products

• 1422459-35-5 C₃₉H₄₄FN₃O₄ 
• 194993-66-3 [4-(12-Bromo-dodecyloxy)-phenyl]-(4-fluoro-phenyl)-diazene 
• 51788-91-1 (E)-1-(4-fluorophenyl)-2-(4-methoxyphenyl)diazene 
• 582310-30-3 N₂-(4-fluorophenyl)-4-methoxybenzene-1,2-diamine 
• 76630-35-8 4-(4'-n-butyloxybenzoyloxy)phenylazo-4''-fluorobenzene 
• 76630-33-6 C₂₀H₁₅FN₂O₃ 
• 76630-37-0 C₂₇H₂₉FN₂O₃ 

Relevant academic research and scientific papers

Synthesis and anticancer activities of 4-[(Halophenyl)diazenyl]phenol and 4-[(Halophenyl)diazenyl]phenyl aspirinate derivatives against nasopharyngeal cancer cell lines

Aspirin and azo derivatives have been widely studied and have drawn considerable attention due to diverse biological activities. In this study, a series of 4-[(halophenyl)diazenyl]phenyl aspirinate derivatives were synthesized from the reaction of aspirin

The selective synthesis ofN-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents

The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles orN-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid providedN2-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles as the major product. A possible reaction mechanism explaining the selectivity was also discussed.

New generation of nitrite functionalized star-like polyvinyl imidazolium compound: Application as a nitrosonium source and three dimensional nanocatalyst for the synthesis of azo dyes

The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.

A New Benzannulation Reaction of Azoaromatics

The BHQ benzannulation reaction of azo-substituted (2-allylaryl)trichloracetates, leading to azo-naphthalenes, is described. The scope and limitations of this new synthesis of azoaromatics is discussed.

Viscoelasticity, dielectric anisotropy, and birefringence in the nematic phase of three four-ring bent-core liquid crystals with an L-shaped molecular frame

Molecular shape is an important factor in determining the material properties of thermotropic liquid crystals (LCs). We synthesized and investigated several LC compounds formed by asymmetrically bent molecules with a rigid four-ring core in the shape of t

Liquid crystalline behavior of binary mixtures of structurally dissimilar mesogens and nonmesogens

We have studied eight binary systems comprising three enantiotropic nematogens, namely 4-(4′-n-butyloxybenzoyloxy)phenylazo-4″- fluorobenzene, 4-(4′-n-butyloxybenzo yloxy)benzylidene-4″-fluoro aniline, and 4-(4′-n-heptyloxybenzoyloxy)phenylazo-4″-fl uorobenzene; a monotropic nematogen, viz. 4-(4′-n-dodecyloxybenzoyloxy) napthylazo-4″-fluorobenzene; and three nonmesogens, viz. 4-(4′-n-butyloxy benzoyloxy)benzalde hyde, 4-methoxybenzylidene-4′- chloroaniline, and 4-methoxybenzylidene-4′-toluidine. The central linkage, terminal group, and central ring system of the components have been varied systematically and the effect of these variations has been evaluated on the liquid crystalline properties of the binary mixtures. The mixed mesomorphic properties of these systems are discussed on the basis of their phase diagrams.

Dinuclear ortho-metallated palladium(II) azobenzene complexes with acetato and chloro bridges: Influence of polar substituents on the mesomorphic properties

The synthesis, characterization and mesomorphic properties of a new series of acetate and chloro-bridged dinuclear orthopalladated complexes derived from azobenzene with terminal groups of hexadecyloxy moiety at one end and different polar groups (Me, Cl, F, NO2, CN) at the other end are described. The mesomorphic properties of both the ligands and complexes were investigated by polarizing optical microscopy and X-ray studies to understand the effect of polar group in the nature of mesophase produced. Among the complexes, all chloro-bridged complexes predominantly exhibited SmA phase. However the rare phenomenon of observing mesomorphism in acetato-bridged palladium (II) complexes due its typical open book shape had been realized in substituted acetato-bridged complexes with fluoro and cyano substituents in the ligands. Nitro and cyano substituted ligands only exhibited monotropic Smectic A phase. Model molecular arrangement based on X-ray studies is presented.

Fluorine-substituted azobenzene destabilizes polar form of optically switchable fulgimide unit in copolymer system

Fulgimide and various size and electronic nature of substituents on the terminal position of azobenzene in the pendant homo/copolymethacrylates were synthesized. Differential scanning calorimetry analysis indicates the homopolymer possessing C-form fulgimide unit exhibited higher Tm than that of E-form of the homopolymer and revealed C-form is highly ordered. Thermal stability suggests azobenzene homopolymers with electron donating substituents have high thermal stability than electron withdrawing substituents. Polarized optical microscopy observation disclosed homopolymers viz., NI, CY, FL, ME, and T-ME exhibited liquid crystalline mesophases between their Tm and Ti. Optical properties of homo/copolymers were investigated by UV-vis and fluorescence spectroscopy. UV-vis spectroscopy displayed C-form fulgimide absorption in F-co-FL around 482 nm which is around 40 nm lesser than C-form of substituted azobenzene copolymers. Similarly, fluorescence pattern of F-co-FL by UV irradiation exhibited emission intensity slowly increased to certain level then decreases with two new emissions at 430 and 480 nm attributed to terminal position of fluorine atom on azobenzene destabilizes polar form (C-form) fulgimide unit in the copolymer.

Effect of lateral substitution on mesogenic properties of fluoro aniline derivatives

Three new homologous series of liquid crystals with terminal fluoro group and central linkages such as ester and azo groups were synthesized and their mesomorphic properties were studied. All three series are similar in molecular structure with the difference in their lateral substitutions: series I has no lateral substitution, series II has a chloro group as lateral substitution, and series III has a methyl group as lateral substitution. All 12 homologues of each of the series are mesogenic in nature. The nematic phase of the series shows a marble texture and the smectic phase shows a Schlieren texture of the smectic C variety. The mesomorphic characteristics of the series are compared with each other. Copyright Taylor & Francis Group, LLC.

Syntheses of Azobenzene Derivatives Having Fluoroalkyl Chain and Their Monomolecular Film Formation at the Air/Water Interface

The compounds, 4-(nonafluorobutyl)aniline, 4-(tridecafluorohexyl)aniline, and 4-(heptadecafluorooctyl)aniline were prepared by the reaction of corresponding perfluoroalkyl iodide with 4-iodoaniline in the presence of copper bronze.Six azobenzene derivatives (4-(4-fluorophenylazo)phenol, F(C6H4)N=N(C6H4)OH (1) (C6H4=p-phenylene), 4-(trifluoromethylphenylazo)phenol, CF3(C6H4)N=N(C6H4)OH (2), 4-(4-heptafluoropropylphenylazo)phenol, C3F7(C6H4)N=N(C6H4)OH (3), 4-(4-nonafluorobutylphenylazo)phenol, C4F9(C6H4)N=N(C6H4)OH (4), 4-(4-tridecafluorohexylphenylazo)phenol, C6F13(C6H4)N=N(C6H4)OH (5), and 4-(4-heptadecafluorooctylphenylazo)phenol, C8F17(C6H4)N=N(C6H4)OH (6)) were prepared by the usual diazo coupling reactions using 4-(perfluoroalkyl)aniline and phenol.The monomolecular film formations of the azobenzene derivatives at the air/water interface were investigated by surface pressure measurements to be dependent on the fluoroalkyl chain length (n).The compounds 5 (n=6) and 6 (n=8) formed stable monomolecular films at the air/water interface.