4128-71-6

Basic information

• Product Name: PARA-ACETAMIDOAZOBENZENE
• Synonyms: PARA-ACETAMIDOAZOBENZENE;PARA-ACETAMIDOBENZENE;4-(Acetylamino)azobenzene;N-(Azobenzene-4-yl)acetamide;N-[4-(Phenylazo)phenyl]acetamide
• CAS NO: 4128-71-6
• Molecular Formula: C₁₄H₁₃N₃O
• Molecular Weight: 239.30
• Mol File: 4128-71-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 145°C
• Boiling Point: 381.93°C (rough estimate)
• Flash Point: 233.3°C
• Appearance: /
• Density: 1.1240 (rough estimate)
• Vapor Pressure: 1.01E-08mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: PARA-ACETAMIDOAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: PARA-ACETAMIDOAZOBENZENE(4128-71-6)
• EPA Substance Registry System: PARA-ACETAMIDOAZOBENZENE(4128-71-6)

Safety Data

• Hazardous Substances Data: 4128-71-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13N3O/c1-11(18)15-12-7-9-14(10-8-12)17-16-13-5-3-2-4-6-13/h2-10H,1H3,(H,15,18)/b17-16+

Upstream product

• 108-24-7 acetic anhydride 
• 60-09-3 aniline yellow 
• 507-09-5 thioacetic acid 
• 19689-51-1 N-(4-(2-phenylhydrazinyl)phenyl)acetamide 
• 28712-12-1 1-acetyl-3-methyl-1H-imidazol-3-ium chloride 
• 22287-69-0 4-phenylazo-phenyl isocyanide 
• 64-19-7 acetic acid 
• 145494-07-1 N-(4,4'-bis-dimethylamino-benzhydryl)-4-phenylazo-aniline 
• 127-09-3 sodium acetate 
• 54915-74-1 1,4-bis-(N'-phenyl-hydrazino)-benzene 

Downstream Products

• 4504-08-9 p-nitrophenyl-N,N,O-azoxybenzene 
• 13921-68-1 β-p-nitroazoxybenzene 
• 62-53-3 aniline 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 1048037-23-5 bis(4-isothiocyanatophenyl)amine 
• 17867-12-8 bis-(4-benzylidenamino-phenyl)-amine 
• 16868-20-5 2-chloro-4-phenylazo-aniline 
• 108272-17-9 N-acetyl-4,4'-diaminodiphenylamine 
• 4845-15-2 acetic acid-(4-methyl-4-phenylazo-anilide) 
• 537-65-5 4,4'-diaminodiphenylamine 
• 106-50-3 1,4-phenylenediamine 
• 22608-33-9 4-Acetylamino-3-chlor-azobenzol 
• 62450-04-8 acetic acid-[4-(phenyl-NNO-azoxy)-anilide] 

Relevant articles and documents

Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications

In this paper we conducted an extensive reactivity study to determine the key structural features that favour the dithionite-triggered reductive cleavage of the azo-arene group. Our stepwise investigation allowed identification of a highly reactive azo-arene structure 25 bearing a carboxylic acid, at the ortho position of the electron-poor arene and an ortho-Oalkyl-resorcinol as the electron-rich arene. Based on this 2(2′-alkoxy-4′-hydroxyphenylazo) benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo-arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo-arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were obtained in biological media.