176752-00-4

Basic information

• Product Name: 3-oxo-2-(phenylhydrazono)butanenitrile
• Synonyms: 3-oxo-2-(phenylhydrazono)butanenitrile
• CAS NO: 176752-00-4
• Molecular Formula: C₁₀H₉N₃O
• Molecular Weight: 187.19796
• Mol File: 176752-00-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-oxo-2-(phenylhydrazono)butanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxo-2-(phenylhydrazono)butanenitrile(176752-00-4)
• EPA Substance Registry System: 3-oxo-2-(phenylhydrazono)butanenitrile(176752-00-4)

Safety Data

• Hazardous Substances Data: 176752-00-4(Hazardous Substances Data)

Upstream product

• 1118-61-2 3-Aminocrotononitrile 
• 62-53-3 aniline 
• 60083-22-9 ethyl (2E)-3-oxo-2-(2-phenylhydrazinylidene)butanoate 
• 1118-60-1 3-iminobutyronitrile 
• 297766-64-4 1,3-Diphenyltriazen 

Downstream Products

• 124315-52-2 4-methyl-6-oxo-1-phenyl-1,6-dihydropyridazine-3,5-dicarbonitrile 

Relevant articles and documents

Discovery of a new class of sortase a transpeptidase inhibitors to tackle gram-positive pathogens: 2-(2-phenylhydrazinylidene)alkanoic acids and related derivatives

A FRET-based random screening assay was used to generate hit compounds as sortase A inhibitors that allowed us to identify ethyl 3-oxo-2-(2-phenylhydrazinylidene)butanoate as an example of a new class of sortase A inhibitors. Other analogues were generated by changing the ethoxycarbonyl function for a carboxy, cyano or amide group, or introducing substituents in the phenyl ring of the ester and acid derivatives. The most active derivative found was 3-oxo-2-(2-(3,4dichlorophenyl)hydrazinylidene)butanoic acid (2b), showing an IC50 value of 50 μM. For a preliminary assessment of their antivirulence properties the new derivatives were tested for their antibiofilm activity. The most active compound resulted 2a, which showed inhibition of about 60% against S. aureus ATCC 29213, S. aureus ATCC 25923, S. aureus ATCC 6538 and S. epidermidis RP62A at a screening concentration of 100 μM.

A microwave assisted diazo coupling reaction: The synthesis of alkylazines and thienopyridazines

Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c. Copyright Taylor & Francis Group, LLC.