17745-84-5

Basic information

• Product Name: N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide)
• Synonyms: N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide);N,N'-[Azinobismethylidynebis(4,1-phenylene)]bisacetamide;Einecs 241-740-6;4-ACETAMIDOBENZALDEHYDE AZINE
• CAS NO: 17745-84-5
• Molecular Formula: C₁₈H₁₈N₄O₂
• Molecular Weight: 324.377
• EINECS: 241-740-6
• Mol File: 17745-84-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 309-310 °C (decomp)
• Boiling Point: 590.6°Cat760mmHg
• Flash Point: 311°C
• Appearance: /
• Density: 1.16g/cm³
• PKA: 14.40±0.70(Predicted)
• CAS DataBase Reference: N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide)(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide)(17745-84-5)
• EPA Substance Registry System: N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide)(17745-84-5)

Safety Data

• Hazardous Substances Data: 17745-84-5(Hazardous Substances Data)

Usage

General Description

N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide) is a chemical compound with the molecular formula C18H20N4O2. It is commonly used as a radical initiator in polymerization reactions, specifically in the production of acrylamide-based polymers. N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide) is a diazonium salt that decomposes under certain conditions to generate free radicals, which then initiate the polymerization process. It is a white to off-white powder that is sparingly soluble in water and has a melting point of around 170-173°C. N,N'-[azinobis(methylidyne-4,1-phenylene)]bis(acetamide) is also known by its trade name V-50, and it is important to handle it with caution due to its potential to decompose and release toxic fumes when heated.

Upstream product

• 51203-02-2 bis-(4-amino-benzylidene)-hydrazine 
• 108-24-7 acetic anhydride 
• 122-85-0 para-acetamidobenzaldehyde 
• 104-06-3 N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide 

Downstream Products

• 117123-85-0 3,7-bis-(4-acetylamino-phenyl)-tetrahydro-[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithione 

Relevant articles and documents

Further Insights into the Oxidative Pathway of Thiocarbonyl-Type Antitubercular Prodrugs: Ethionamide, Thioacetazone, and Isoxyl

A chemical activation study of the thiocarbonyl-type antitubercular prodrugs, ethionamide (ETH), thioacetazone (TAZ), and isoxyl (ISO), was performed. Biomimetic oxidation of ethionamide using H2O2 (1 equiv) led to ETH-SO as the only stable S-oxide compound, which was found to occur in solution in the preferential form of a sulfine (ETH=S=O vs the sulfenic acid tautomer ETH-S-OH), as previously observed in the crystal state. It was also demonstrated that ETH-SO is capable of reacting with amines, as the putative sulfinic derivative (ETH-SO2H) was supposed to do. Unlike ETH, oxidation of TAZ did not allow observation of the mono-oxygenated species (TAZ-SO), leading directly to the more stable sulfinic acid derivative (TAZ-SO2H), which can then lose a SOxH group after further oxidation or when placed in a basic medium. It was also noticed that the unstable TAZ-SO intermediate can lead to the carbodiimide derivative as another electrophilic species. It is suggested that TAZ-SOH, TAZ-SO2H, and the carbodiimide compound can also react with NH2-containing nucleophilic species, and therefore be involved in toxic effects. Finally, ISO showed a very complex reactivity, here assigned to the coexistence of two mono-oxygenated structures, the sulfine and sulfenic acid tautomers. The mono- and dioxygenated derivatives of ISO are also highly unstable, leading to a panel of multiple metabolites, which are still reactive and likely contribute to the toxicity of this prodrug.