2496-25-5

Basic information

• Product Name: Phenol, p-((p-Methoxyphenyl)azo)-
• Synonyms: Phenol, p-((p-Methoxyphenyl)azo)-;4-((Methoxyphenyl)diazenyl)phenol;4-[(p-Hydroxyphenyl)azo]anisole];NSC 3289;p-Hydroxy-p'-methoxyazobenzene
• CAS NO: 2496-25-5
• Molecular Formula: C₁₃H₁₂N₂O₂
• Molecular Weight: 228.24658
• Mol File: 2496-25-5.mol

Chemical Properties

• Melting Point: 149.8℃ (methanol water )
• Boiling Point: 368.1°Cat760mmHg
• Flash Point: 176.4°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 1.3E-05mmHg at 25°C
• Refractive Index: 1.578
• PKA: 8.81±0.15(Predicted)
• CAS DataBase Reference: Phenol, p-((p-Methoxyphenyl)azo)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, p-((p-Methoxyphenyl)azo)-(2496-25-5)
• EPA Substance Registry System: Phenol, p-((p-Methoxyphenyl)azo)-(2496-25-5)

Safety Data

• Hazardous Substances Data: 2496-25-5(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
Phenol, p-((p-Methoxyphenyl)azo)is used as an indicator for the spectrophotometric determination of aluminium, forming a red complex with aluminium ions in slightly acidic solutions. This characteristic makes it a valuable tool in the analysis of aluminium content in various samples.
Used in Environmental Analysis:
Phenol, p-((p-Methoxyphenyl)azo)is also utilized in the development of a sensitive and selective flow injection analysis system for the determination of beryllium, contributing to the accurate measurement of this element in environmental samples.
Used in Environmental Monitoring:
Due to its potential as an environmental pollutant, Phenol, p-((p-Methoxyphenyl)azo)is used in monitoring and managing the presence of harmful substances in the environment. Careful use and handling are essential to minimize any adverse effects on human health and the environment.

InChI:InChI=1/C13H12N2O2/c1-17-13-8-4-11(5-9-13)15-14-10-2-6-12(16)7-3-10/h2-9,15H,1H3

Upstream product

• 17333-79-8 p-methoxybenzenediazonium 
• 108-95-2 phenol 
• 104-94-9 4-methoxy-aniline 
• 17478-80-7 (4-methoxyphenyl)phenyldiazene 1-oxide 
• 17478-75-0 N'-(4-methoxy-phenyl)-N-phenyl-diazene-N-oxide 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 100-17-4 para-methoxynitrobenzene 
• 103-90-2 4-acetaminophenol 
• 123-30-8 4-amino-phenol 
• 51-66-1 4-methoxyacetanilide 
• 20265-97-8 p-anisidine hydrochloride 
• 139-02-6 sodium phenoxide 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 127040-10-2 1-(4-methoxy-phenylazo)-4-stearoyloxy-benzene 
• 91454-73-8 4-methoxy-4'-ethoxyazobenzene 
• 26053-96-3 4-acetoxy-4'-methoxyazobenzene 
• 58586-46-2 4-acryloyloxy-4'-methoxyazobenzene 
• 144225-85-4 4-(2-Hydroxy-ethyloxy)-4'-methoxy-azobenzen 
• 101969-92-0 4-(4-methoxy-phenylazo)phenoxy methacrylate 
• 145344-52-1 1-bromo-4-(4-methoxyazobenzene-4'-oxy)butane 
• 132458-37-8 1-bromo-6-(4-(4-methoxyphenyl)azobenzene-1-oxy)hexane 
• 149474-78-2 1-(4-((8-bromooctyl)oxy)phenyl)-2-(4-methoxyphenyl)diazene 
• 129779-34-6 4-(3-{3-[4-(4-Methoxy-phenylazo)-phenoxycarbonyl]-propyl}-1,1,3,3-tetramethyl-disiloxanyl)-butyric acid 4-(4-methoxy-phenylazo)-phenyl ester 

Relevant articles and documents

Low-temperature nematic phase in azo functionalised reactive hockey stick mesogens possessing lateral methyl group

We report, the design, synthesis and mesomorphic behaviour of new hockey stick mesogens containing photochromic azo group and a reactive double bond. The structure of the compounds resemble the hockey stick due to unequal distribution of the phenyl rings

Photoisomerization and Mesophase Formation in Azo-Ionic Liquids

Ionic liquids present a versatile, highly tunable class of soft functional materials. Aside from being low melting salts, they can be endowed with additional functionalities. In N-alkylimidazolium halides, which are a prominent class of ionic liquids (ILs), the imidazolium cation was linked via an ether-bridge to an azobenzene unit in order to obtain photoresponsive materials through photoinduced trans-cis isomerization. The azobenzene unit, in turn, was modified with electron-donating or -withdrawing groups such as methyl-, tert-butyl-, methoxy-, N,N-dimethylamino, and nitro groups to study their influence on the photoisomerization and phase behavior. Endowing the imidazolium additionally with a long alkyl chain allows the materials to potentially form liquid crystalline (LC) mesophases before melting into the isotropic liquid. All studied compounds qualify as ionic liquids, and all, except for the nitro-compound, show the formation of smectic mesophases melting to the isotropic liquid. The compounds with the bulkiest aliphatic substituent, the tert-butyl, shows the lowest melting point, the largest mesophase window, and an efficient photochemical trans-cis conversion (>90%). In summary, by tuning sterically and electronically the cationic part of ILs, a photoswitchable room temperature liquid crystal could be developed and design guidelines for photoresponsive ionic liquids could be obtained.

The role of conductivity and molecular mobility on the photoanisotropic response of a new azo-polymer containing sulfonic groups

We report the preparation of a new light-responsive side-chain terpolymer containing azobenzenes, as chromophoric components, sulfonic groups, as polar components, and methacrylate groups, as film forming components, and we provide a detailed characterisa

A Novel Side-Chain Liquid Crystal Elastomer Exhibiting Anomalous Reversible Shape Change

Liquid crystalline elastomers (LCEs) have been actively investigated as stimuli-controlled actuators and soft robots. The basis of these applications is the ability of LCEs to undergo a reversible shape change upon a liquid crystalline (LC)-isotropic phas

Structure modification of an active azo-compound as a route to new antimicrobial compounds

Some novel (phenyl-diazenyl)phenols 3a-g were designed and synthesized to be evaluated for their antimicrobial activity. A previously synthesized molecule, active against bacteria and fungi, was used as lead for modifications and optimization of the structure, by introduction/removal or displacement of hydroxyl groups on the azobenzene rings. The aim of this work was to evaluate the consequent changes of the antimicrobial activity and to validate the hypothesis that, for these compounds, a plausible mechanism could involve an interaction with protein receptors, rather than an interaction with membrane. All newly synthesized compounds were analyzed by 1H-NMR, DSC thermal analysis and UV-Vis spectroscopy. The in vitro minimal inhibitory concentrations (MIC) of each compound was determined against Gram-positive and Gram-negative bacteria and Candida albicans. Compounds 3b and 3g showed the highest activity against S. aureus and C. albicans, with remarkable MIC values of 10 μg/mL and 3 μg/mL, respectively. Structure-activity relationship studies were capable to rationalize the effect of different substitutions on the phenyl ring of the azobenzene on antimicrobial activity.

Thermostable birefringent copolyimide films based on azobenzene-containing pyrimidine diamines

Azobenzene (azo)-containing polymers have attracted continuous attention due to their excellent photosensitivity. However, practical applications of their photo-induced birefringence have been hampered by low thermal stability. In this work, we report a s

Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer

The invention discloses synthesis of a diamine monomer with azo and polyimide prepared from the diamine monomer. The structural formula of the polyimide is shown in the specification. The polyimide is synthesized through polycondensation of the diamine mo

Photoswitchable NIR-Emitting Gold Nanoparticles

Photo-switching of the NIR emission of gold nanoparticles (GNP) upon photo-isomerization of azobenzene ligands, bound to the surface, is demonstrated. Photophysical results confirm the occurrence of an excitation energy transfer process from the ligands to the GNP that produces sensitized NIR emission. Because of this process, the excitation efficiency of the gold core, upon excitation of the ligands, is much higher for the trans form than for the cis one, and t→c photo-isomerization causes a relevant decrease of the GNP NIR emission. As a consequence, photo-isomerization can be monitored by ratiometric detection of the NIR emission upon dual excitation. The photo-isomerization process was followed in real-time through the simultaneous detection of absorbance and luminescence changes using a dedicated setup. Surprisingly, the photo-isomerization rate of the ligands, bound to the GNP surface, was the same as measured for the chromophores in solution. This outcome demonstrated that excitation energy transfer to gold assists photo-isomerization, rather than competing with it. These results pave the road to the development of new, NIR-emitting, stimuli-responsive nanomaterials for theranostics.

Method for preparing polyimide polymer with azo-pyrimidine structure unit

The invention relates to a method for preparing a diamine monomer with an azo-pyrimidine structure and a method for preparing a polyimide polymer by adopting the diamine monomer with the azo-pyrimidine structure. The preparation method comprises the following steps: carrying out a coupling reaction on 4-substituted aniline and sodium phenate to obtain 4-hydroxy-4'-substituted azobenzene; and carrying out nucleophilic substitution on the 4-hydroxy-4'-substituted azobenzene and dibromoalkane to generate bromo-azobenzene, and reacting the bromo-azobenzene with 4,6-diamido-2-mercaptopyrimidine to obtain the diamine monomer; and carrying out condensation polymerization on the diamine monomer with dianhydride to obtain polyimide. The pyrimidine structure is introduced into the diamine monomer, so that the charge transfer complex effect of aromatic rings of polyimide is reduced, and the glass transition temperature of the polyimide is reduced; and the azo group has photo-induced anisotropy, and an azo unit is introduced into the polyimide by alkyl chains having different lengths, so that the heterogeneous degree of the azo group can be effectively regulated, and the application of the polyimide in alignment films and other optical fields can be improved to a great extent.

Mesomorphism of azo-esters and chalcone-esters

AOne chalcone-ester homologous series of mesogens α-4-[4/-n-alkoxybenzoyloxy phenyl β-4//methoxy benzoyl ethylenes (A) and one azo-ester homologous series of mesogens p-(p/-n-alkoxybenzoyloxy) phenyl azo-p//-methoxy benzene (B) being structurally similar are discussed. Both series (A) and (B) differ in respect of central bridges linking two phenyl rings. Mesomorphic properties start from 6th and 1st member of series (A) and (B) respectively. In series (A), 6th to 12th members show both smectogenic and nematogenic properties, and the 14th and 16th members show only nematogenic property. While in series (B), 1st to 10th members show nematogenic properties, 11th member shows both smectogenic and nematogenic properties, while 12th member shows only smectogenic property. Thermal stability of series (A) is relatively high as compared to series (B). Transition temperatures are observed through hot stage polarizing microscope by the miscibility method. Analytical data support the structure of molecules. Textures of series (A) in nematic are threaded and Schlieren in SmecticSmectic A type, while that of series (B) in nematic are threaded in SmecticSmectic A and smectic C.