34938-47-1

Basic information

• Product Name: 2-(phenylazo)-1H-imidazole
• Synonyms: 2-(phenylazo)-1H-imidazole
• CAS NO: 34938-47-1
• Molecular Formula: C₉H₈N₄
• Molecular Weight: 172.18662
• EINECS: 252-298-9
• Mol File: 34938-47-1.mol

Chemical Properties

• Boiling Point: 349.7 °C at 760 mmHg
• Flash Point: 165.3 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 2-(phenylazo)-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(phenylazo)-1H-imidazole(34938-47-1)
• EPA Substance Registry System: 2-(phenylazo)-1H-imidazole(34938-47-1)

Safety Data

• Hazardous Substances Data: 34938-47-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(Phenylazo)-1H-imidazole serves as a key intermediate in organic synthesis, facilitating the creation of a variety of complex organic molecules. Its ability to form stable complexes with metal ions enhances its utility in this domain.
Used as a Ligand in Coordination Chemistry:
In coordination chemistry, 2-(Phenylazo)-1H-imidazole acts as a ligand, participating in the formation of coordination compounds. Its structural features allow it to chelate metal ions, which is crucial for the development of new materials with specific properties.
Used in the Development of New Materials:
2-(phenylazo)-1H-imidazole's unique properties and reactivity make it a candidate for the development of innovative materials. Its potential applications extend to various fields, including the creation of advanced materials with tailored characteristics for specialized uses.
Used in Pharmaceutical Development:
Due to its ability to interact with metal ions and its presence in coordination compounds, 2-(Phenylazo)-1H-imidazole holds promise in the pharmaceutical industry. It may contribute to the design of new drugs or drug delivery systems that leverage its chemical interactions.
Used in Organic Light-Emitting Diodes (OLEDs):
2-(Phenylazo)-1H-imidazole has been studied for its potential use in the field of OLEDs. Its incorporation could enhance the performance of these devices, contributing to the advancement of display and lighting technologies.
Used in Dye-Sensitized Solar Cells:
2-(phenylazo)-1H-imidazole is also considered for use in dye-sensitized solar cells, where its light-absorbing and energy-transfer properties could improve the efficiency and performance of these renewable energy devices.

InChI:InChI=1/C9H8N4/c1-2-4-8(5-3-1)12-13-9-10-6-7-11-9/h1-7,12H

Upstream product

• 288-32-4 1H-imidazole 
• 100-34-5 benzene diazonium chloride 
• 62-53-3 aniline 

Downstream Products

• 86027-01-2 1-Methoxy-3-(2-phenylazo-imidazol-1-yl)-propan-2-ol 
• 583879-18-9 (E)-1-ethyl-2-(phenylazo)imidazole 
• 93937-86-1 (E)-1-methyl-2-(phenylazo)imidazole 
• 7720-39-0 1H-imidazol-2-amine 
• 113-00-8 guanidine nitrate 
• 62-53-3 aniline 
• 96139-65-0 4-(4-amino-phenyl)-1⁽³⁾H-imidazol-2-ylamine 
• 615584-13-9 C₃₀H₂₈N₄O₅ 
• 65146-52-3 2-amino-4-(4-aminophenyl)imidazole dihydrochloride 
• 1356032-45-5 [zinc(II)(imidazolate)(2-phenylazoimidazolate)] 
• 1352391-65-1 N⁽¹⁾-n-hexyl-2-pheylazoimidazole 
• 1352391-61-7 N⁽¹⁾-n-butyl-2-pheylazoimidazole 
• 1352391-69-5 N⁽¹⁾-n-octyl-2-pheylazoimidazole 
• 1400923-74-1 Cu(triphenylphosphine)(2-(phenylazo)imidazole)I 

Relevant articles and documents

Properties and applications of designable and photo/redox dual responsive surfactants with the new head group 2-arylazo-imidazolium

2-Arylazo-imidazolium was investigated as a new hydrophilic head group for ionic liquid surfactants. With the azo moiety at the 2-C site of imidazolium, it was designed to expand the extensibility of the functionalization and controllability of assembly. Structural designability was displayed by the colloidal chemical properties like surface tension, conductivity and steady fluorescence quenching of the designed surfactants. Their corresponding responsiveness towards photo stimuli was compared. Further properties like the reversible electrochemical redox responsiveness and the instinctive fluorescence of the designed surfactants were discovered. A potential application was demonstrated by the photo-controllable fabrication of Au nanostars.

New, facile approach to biologically significant and functionalizable heterobiaryls

An "intellectual connection" approach and a novel route to suitably substituted and functionalizable heterobiaryls of biological significance, involving diazonium trapping by an imidazole and 1,2,4-triazole and subsequent heterocyclic benzidine type of rearrangement is reported. Copyright Taylor & Francis Group, LLC.

Influence of the cavity size of cyclodextrins on the photochromism of azoimidazoles

1-Alkyl-2-(arylazo)imidazole (RaaiR/) exists in trans configuration about the –N[dbnd]N- bond. Upon optical excitation in UV region the trans-configuration isomerises to cis-RaaiR/. The photochromism is very susceptible to internal substituents and external environment like solvent polarity, viscosity and presence of innocent foreign species. In this work, the trans-to-cis photoisomerisation of RaaiR/has been studied in DMF solution of cyclodextrin (α/β/γ-CD). The rate of trans-to-cis isomerisation is decreased in presence of CD compared to native form of RaaiR/. The quantum yield of the photoisomerisation is decreased by 35–55% in inclusion phase, CD@RaaiR/, than free photochrome and follows the rate sequence: free state > γ-cyclodextrin > β-cyclodextrin > α-cyclodextrin. The cis-to-trans isomerisation proceeds slowly in visible light irradiation while it is appreciably fast with increasing temperature. The activation energy (Ea) of cis → trans thermal isomerisation is also diminished compared to free state of photochrome. The absorption spectral studies have been used in case of Pai-C18H37 with β-CD and inclusion constant is Kb ?= ?0. 121 M?1. The 1H NMR spectral measurement also suggests interaction of aryl protons with cavity protons of β-CD. DFT computation is also attempted to examine the inclusion of RaaiR/with CD and the negative values of binding energy show that the process of inclusion is spontaneous and complexes formed are stable.

The synthesis, structure and photochromism of mercury(II)-iodide complexes of 1-CnH2n+1-2-(arylazo)imidazoles (n = 4, 6, 8)

The reaction of HgI2 with 1-CnH2 n+1-2-(arylazo)imidazole (Raai-CnH 2n+1 where n = 4, 6, 8) has isolated iodide bridging dimeric complexes, [Hg(RaaiCnH2n +1)(μ-I)(I)]2. The structures of the ligand and the complexes have been established by spectral (UV-Vis, IR, 1H NMR) data. One of these complexes [Hg(1-hexyl-2-(p-tolylazo)imidazole)(μ-I)(I)] 2 has been structurally confirmed by single crystal X-ray diffraction study. The ligand, Raai-CnH2n+1 exists at ambient condition in trans geometry about azo (-NN-) group; the UV light irradiation in MeOH solution shows E-to-Z isomerisation. The reverse transformation, Z-to-E, is very slow with visible light irradiation while isomerises rapidly on heating. The coordinated ligand, Raai-CnH 2n+1 in the complexes exhibit similar behaviour in DMF solution. Quantum yields (φE→ Z) of E-to-Z isomerisation are higher for free ligands than that of their metal complexes. The Z-to-E isomerisation is a thermally induced process. The activation energy (Ea) is calculated by controlled temperature experiment.

A facile and new approach to synthesize 2-amino-4-(4-amoinophenyl)-1H-1,3- diazol-1-yl-alkylaminomethanethiones

An "intellectual connection" approach to design a facile and new synthesis of suitably substituted 2-aminoimidazole-based precursors of expected anti-asthmatic agents through a benzidine type of rearrangement of 2-phenylazoimidazole and subsequent coupling of the product thus obtained with alkylisothiocyanates involving a degenerative operation, thereby improving the time frame of the overall synthetic sequence, is reported. The alkylisothiocyanates required in this synthetic sequence are prepared using a best combination of reported methods. The compounds reported here can be used to produce derivatives of other biological agents. Birkhaeuser 2007.

Synthesis and pharmacological activities of some mononuclear Ru(II) complexes

A series of mononuclear Ru(II) complexes of the type [Ru(M) 2(U)]2+, where M=2,2′-bipyridine/1,10-phenanthroline and U=tpl (Ru1), 4-Cl-tpl (Ru2), 4-CH3-tpl (Ru3), 4-CH 3O-tpl (Ru4), and 4-NO2-tpl (Ru5), -pai (Ru6), where tpl = thiopicolinanilide and pai = 2-phenyl-azo-imidazole, have been prepared and characterized by IR, UV-Vis, 1H NMR, 13C-NMR, FAB-Mass spectrophotometer, and elemental analysis. The complexes display metal-ligand charge transfer (MLCT) transitions in the visible region. The title complexes were subjected to in vivo anticancer activity tests against a transplantable murine tumor cell line, Ehrlich's ascitic carcinoma (EAC) and in vitro antibacterial activity against Gram positive and Gram negative microorganisms. Ru1-Ru6 were found to increase the life span of the tumor hosts by 19-52%, and decreased tumor volume and viable ascitic cell count. The results of the present study clearly demonstrated the tumor inhibitory activity of the ruthenium chelates against transplantable murine tumor cell line. The treatment with ruthenium complexes could be secondary to tumor regression or due to the action of the compounds itself. The significant antibacterial activity was observed for Ru1-Ru4 against microorganisms like Vibrio cholera 865, Staphylococcus aureus 6571, and Shigella flexneri as compared to that of standard drug chloramphenical. Ru5 showed moderate activity against S. aureus 8530. However, all the complexes fail to show significant antibacterial activity against V. cholera 14033 and Shigella sonnai.

2,4-Bis(phenylazo)aniline as a By-Product of Azo Coupling of Aniline with Imidazole

2,4-Bis(phenylazo)aniline was isolated as a by-product of the synthesis of 2-(phenylazo)imidazole by azo coupling of diazotized aniline with imidazole. The formation of the former is explained by involvement of 1,3-diphenyltriazene in the reaction and by catalytic effect of the imidazole.

Synthesis and spectral characterization of lead(II), silver(I), palladium(II) and dioxouranium(VI) azoimidazole complexes

A few complexes of Pb(II), Ag(I), Pd(II) and dioxouraniura(VI) with arylazoimidazoles have been synthesized and characterized by elemental analyses, IR, UV/VIS, 1H NMR and conductance studies. The uranyl complexes are found to be monomeric and ionic in nature whereas Pb(II), Ag(I) and Pd(II) complexes are polymeric.