59394-93-3

Basic information

• Product Name: Benzoic acid [1-(4-bromo-phenyl)-meth-(E)-ylidene]-hydrazide
• Synonyms: Benzoic acid [1-(4-bromo-phenyl)-meth-(E)-ylidene]-hydrazide
• CAS NO: 59394-93-3
• Molecular Weight: 303.158
• Mol File: 59394-93-3.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Benzoic acid [1-(4-bromo-phenyl)-meth-(E)-ylidene]-hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid [1-(4-bromo-phenyl)-meth-(E)-ylidene]-hydrazide(59394-93-3)
• EPA Substance Registry System: Benzoic acid [1-(4-bromo-phenyl)-meth-(E)-ylidene]-hydrazide(59394-93-3)

Safety Data

• Hazardous Substances Data: 59394-93-3(Hazardous Substances Data)

Upstream product

• 613-94-5 benzoic acid hydrazide 
• 1122-91-4 4-bromo-benzaldehyde 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 1242282-86-5 diethyl 2-[(E)-1-benzoyl-2-(4-bromobenzylidene)hydrazinyl]fumarate 
• 21510-43-0 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole 
• 17453-23-5 2-(4-bromophenyl)-5-phenyl-1,3,4-thiadiazole 
• 957045-51-1 2-phenyl-5-[4-(phenylethynyl)phenyl]-1,3,4-oxadiazole 
• 1448781-80-3 ((3R,3aS,6aS)-3-(4-bromophenyl)-2,3,3a,4-tetrahydrocyclopenta[c]pyrazol-1(6aH)-yl)(phenyl)methanone 
• 1366284-20-9 N-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)benzohydrazide 
• 1333150-37-0 C₁₇H₁₇BrN₂O 
• 1259388-05-0 N'-(1-(4-bromophenyl)-2,2-difluoro-3-oxo-3-phenylpropyl)benzohydrazide 
• 1236309-94-6 C₁₈H₁₅BrN₂O₂ 
• 1191940-79-0 C₁₈H₁₈BrClN₂O₃ 
• 1198616-56-6 C₁₇H₁₇BrN₂O 

Relevant articles and documents

Sodium hypochlorite-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from hydrazides and aldehydes

[Figure not available: see fulltext.] A simple and convenient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed. Structurally divergent symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles can be obtained in moderate to high yields via NaOCl-mediated oxidative cyclization of N-acylhydrazones, generated in situ from aliphatic and aromatic hydrazides and aldehydes.

Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones

The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.

Synthesis of New Alkynyl-Bridged 2,5-Disubstituted 1,3,4-Oxadiazoles

A synthesis of new alkynyl-derived 2,5-disubstituted 1,3,4-oxadiazoles through palladium/copper-catalyzed Sonogashira cross-coupling between oxadiazole-substituted phenyl bromides and various arylacetylenes is described. Investigation of the absorption and emission spectra of the target compounds indicates emission profiles in the near-blue and blue region and high luminescence intensities. The presented approach is very convenient for the synthesis of luminescent small-molecules or precursors of other complex derivatives that are useful in the preparation of OLEDs as electron-transporting components.