4340-77-6

Basic information

• Product Name: 1-(4-Chlorophenyl)-2-phenyldiazene
• Synonyms: 1-(4-Chlorophenyl)-2-phenyldiazene;4-Chloroazobenzene
• CAS NO: 4340-77-6
• Molecular Formula: C₁₂H₉ClN₂
• Molecular Weight: 0
• Mol File: 4340-77-6.mol
• Article Data: 39

Chemical Properties

• Melting Point: 88°C
• Boiling Point: 350.93°C (rough estimate)
• Appearance: /
• Density: 1.2154 (rough estimate)
• Refractive Index: 1.5749 (estimate)
• Water Solubility: 433.3ug/L(25 oC)
• CAS DataBase Reference: 1-(4-Chlorophenyl)-2-phenyldiazene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chlorophenyl)-2-phenyldiazene(4340-77-6)
• EPA Substance Registry System: 1-(4-Chlorophenyl)-2-phenyldiazene(4340-77-6)

Safety Data

• Hazardous Substances Data: 4340-77-6(Hazardous Substances Data)

Usage

Description

1-(4-Chlorophenyl)-2-phenyldiazene, also known as p-chlorophenylphenyldiazene, is a chemical compound characterized by the molecular formula C12H9ClN2. It is an aromatic diazene, a class of organic compounds that feature a N-N double bond. This yellow crystalline solid is insoluble in water but readily soluble in organic solvents. Its unique properties and reactivity make it a versatile compound in various chemical applications.

Uses

Used in Organic Synthesis:
1-(4-Chlorophenyl)-2-phenyldiazene is utilized as a reagent in organic synthesis for the creation of a variety of chemical compounds. Its presence in reactions can facilitate the formation of desired products, making it a valuable component in the synthesis process.
Used in Chemical Reactions:
As a reagent, 1-(4-Chlorophenyl)-2-phenyldiazene is used in chemical reactions to alter the structure or properties of other compounds. Its reactivity with certain functional groups can lead to the formation of new chemical entities with specific applications.
Used in Synthesis of Azo Dyes:
1-(4-Chlorophenyl)-2-phenyldiazene is employed in the synthesis of azo dyes, which are a class of compounds known for their vibrant colors and used extensively in the dyeing and coloring of fabrics, plastics, and other materials.
Used in Pharmaceutical and Materials Science:
Due to its unique properties, 1-(4-Chlorophenyl)-2-phenyldiazene may have potential applications in the pharmaceutical industry for the development of new drugs. Additionally, its reactivity and structural characteristics could be harnessed in materials science for the creation of novel materials with specific properties.

InChI:InChI=1/C12H9ClN2/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H

Upstream product

• 106-47-8 4-chloro-aniline 
• 64-19-7 acetic acid 
• 586-96-9 Nitrosobenzene 
• 546-67-8 lead(IV) tetraacetate 
• 98-95-3 nitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 108-94-1 cyclohexanone 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 62-53-3 aniline 
• 60-09-3 aniline yellow 
• 108-95-2 phenol 
• 619-97-6 benzenediazonium nitrate 

Downstream Products

• 21737-17-7 2-(4-chloro-phenylazo)-phenol 
• 2703-27-7 4-chloro-4'-hydroxyazobenzene 
• 144499-67-2 4-chloro-2'-heptafluoropropylazobenzene 
• 144499-66-1 4-chloro-4'-heptafluoropropylazobenzene 
• 17478-82-9 β-p-chloroazoxybenzene 
• 43187-53-7 4,4'-dichloroazoxybenzene 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 106-47-8 4-chloro-aniline 
• 62-53-3 aniline 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 36684-65-8 6-chloro-1,2,3,4-tetrahydrocarbazole 

Relevant articles and documents

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes

A copper-catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines for the synthesis of unsymmetrical azoxybenzenes was developed. This approach uses O2 as the oxidant. The reaction products are diverse unsymmetrical azoxybe

Photosensitive and Photoswitchable TRPA1 Agonists Optically Control Pain through Channel Desensitization

Transient receptor potential ankyrin 1 (TRPA1) channel, as a nonselective ligand-gated cation channel robustly in dorsal root ganglion sensory neurons, is implicated in sensing noxious stimuli and nociceptive signaling. However, small-molecule tools targeting TRPA1 lack temporal and spatial resolution, limiting their use for validation of TRPA1 as a therapeutic target for pain. In our previous work, we found that 4,4′-(diazene-1,2-diyl)dianiline (AB1) is a photoswitchable TRPA1 agonist, but the poor water solubility and activity hinder its further development. Here, we report a series of specific and potent azobenzene-derived photoswitchable TRPA1 agonists (series 1 and 2) that enable optical control of the TRPA1 channel. Two representative compounds 1g and 2c can alleviate capsaicin-induced pain in the cheek model of mice through channel desensitization but not in TRPA1 knockout mice. Taken together, our findings demonstrate that photoswitchable TRPA1 agonists can be used as pharmacological tools for study of pain signaling.