16580-57-7

Basic information

• Product Name: (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene
• CAS NO: 16580-57-7
• Molecular Formula: C₁₉H₁₅N₅O₂
• Molecular Weight: 345.3547
• Mol File: 16580-57-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 518.5°C at 760 mmHg
• Flash Point: 267.4°C
• Density: 1.24g/cm³
• Vapor Pressure: 7.42E-11mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene(16580-57-7)
• EPA Substance Registry System: (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene(16580-57-7)

Safety Data

• Hazardous Substances Data: 16580-57-7(Hazardous Substances Data)

Usage

Description

(E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene, also known as 4-Nitroazobenzene, is a chemical compound with the molecular formula C18H13N5O2. It is a yellow to orange crystalline solid that is commonly used as a precursor in the synthesis of dyes and pigments. (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene is known to be toxic and harmful if swallowed, inhaled, or absorbed through the skin, and it is also considered a potential environmental hazard. Due to its potential health and environmental risks, it should be handled and stored with care, and proper safety precautions should be taken when working with this chemical.

Uses

Used in Dye and Pigment Synthesis:
(E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene is used as a precursor in the chemical industry for the synthesis of dyes and pigments. Its unique chemical structure allows for the creation of a variety of colored compounds that can be utilized in various applications, such as in the textile, plastics, and printing industries.
Used in Research and Development:
In the field of scientific research, (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene can be used as a starting material for the development of new compounds with potential applications in various industries. Researchers can explore its chemical properties and reactivity to create novel substances with specific characteristics and uses.
Used in Environmental Monitoring:
Due to its potential environmental hazard, (E)-1-(4-nitrophenyl)-2-[phenyl(2-phenylhydrazinylidene)methyl]diazene can be used in environmental monitoring and assessment programs. By analyzing the presence and concentration of this compound in the environment, researchers and regulatory agencies can better understand its impact on ecosystems and human health, and develop strategies to mitigate any negative effects.

Upstream product

• 14368-49-1 p-nitrobenzenediazonium 
• 588-64-7 benzaldehyde phenylhydrazone 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 728-95-0 phenyl-phenylhydrazono-acetic acid 
• 100-34-5 benzene diazonium chloride 
• 3078-09-9 benzaldehyde p-nitrophenylhydrazone 
• 100-01-6 4-nitro-aniline 
• 100-63-0 phenylhydrazine 
• 100-52-7 benzaldehyde 
• 124051-65-6 2-(4-nitrophenyl)-3,5-diphenyl-2H-tetrazolium chloride 
• 57-14-7 N,N-Dimethylhydrazine 
• 62-53-3 aniline 
• 33786-33-3 anti-benzaldehyde (4'-nitrophenyl)hydrazone 

Downstream Products

• 58174-87-1 2-(4-nitro-phenyl)-3,5-diphenyl-tetrazolium; bromide 
• 55699-51-9 2-(4-Nitro-phenyl)-3,5-diphenyl-3H-tetrazol-2-ium 
• 74121-69-0 1,1-diacetoxy-(C₆H₅)2(C₆H₄NO₂)-1-bora-2,3,5,6-tetrazine 
• 124051-65-6 2-(4-nitrophenyl)-3,5-diphenyl-2H-tetrazolium chloride 

Relevant articles and documents

Chromogenic Reaction of 1,1-Dimethylhydrazine with Aryltetrazolium Salts

The reactions of 1,1-dimethylhydrazine with 2,3,5-triphenyl-2Н-tetrazolium and 2,5-diphenyl-3-(4-nitrophenyl)-2Н-tetrazolium chlorides in a solution and on a cellulose carrier have been studied by means of spectrophotometry and chromato–mass spectrometry to develop new chromogenic indicators for detection of 1,1-dimethylhydrazine. 1,3,5-Triphenylformazan and 1,3-diphenyl-5-(4-nitrophenyl)formazan are formed in these reactions, respectively; deep red shifts have been observed. Other products of these reactions result from oligomerization and addition of short-living 1,1-dimethylhydrazyl and tetrazolium radicals.

Anti-Plasmodium activity of tetrazolium salts

We have previously reported that sulfated cyclodextrins inhibit the invasion of Plasmodium merozoites by interacting with receptors present on the surface of erythrocytes. The observation that tetrazolium salts formed stable complexes with the inhibitory sulfated cyclodextrins suggested that tetrazolium salts might have anti-Plasmodium activity as well. Evaluation of commercially available tetrazolium salts indicated that some were active in the low nanomolar range and showed specificity in their inhibition of Plasmodium. Synthesis of a further 54 structures allowed us to determine that activity results from an aromatic component attached to the tetrazolium carbon atom (R1) and its size is not critical to the activity of the compound. Nitro modifications of active compounds are poorly tolerated, however, the presence of halogen atoms on aromatic groups attached to the nitrogen atoms of the tetrazolium ring (R2 and R3) has little effect on activity. Methoxy groups are tolerated on R2 and R3 components; however, they are disruptive on the R1 component. The overall results suggest that the R1 component is interacting with a specific hydrophobic environment and the R2 and R3 components are less constrained. The activity of these compounds in several human and mouse Plasmodium cultures suggests that the compounds interact with a component of the parasite that is both essential and conserved.

Kinetics and Mechanism of Oxidative Cyclization of Formazans to Tetrazolium Salts by Thallium(III) Acetate

The kinetics of thallium(III) acetate oxidation of 1,3,5-triarylformazans have been investigated in acetic acid-water mixture.The reaction, which leads to tetrazolium salt as the product, follows the rate-law .The effect of substituent in the aldehyde (3-phenyl), the phenylhydrazine (l-phenyl) and the aryldiazonium (5-phenyl) moieties on the reaction rate has been studied and the corresponding Hammett rhos are -0.78, -0.85 and -0.8 respectively.A mechanism for the oxidative cyclization is proposed involving the formation of a N-thallated complex between the formazan and T1 (III) acetate which decomposes in a slow step accompanied by a ring closure between N-1 and N-5.