61543-85-9

Basic information

• Product Name: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]oct-7-ene-2,5-diylidenedihydrazide
• CAS NO: 61543-85-9
• Molecular Formula: C22H24N4O4S2
• Molecular Weight: 472.589
• Mol File: 61543-85-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]oct-7-ene-2,5-diylidenedihydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]oct-7-ene-2,5-diylidenedihydrazide(61543-85-9)
• EPA Substance Registry System: Benzenesulfonic acid, 4-methyl-, bicyclo[2.2.2]oct-7-ene-2,5-diylidenedihydrazide(61543-85-9)

Safety Data

• Hazardous Substances Data: 61543-85-9(Hazardous Substances Data)

Upstream product

• 17660-74-1 bicyclo[2.2.2]oct-7-ene-2,5-dione 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 61543-84-8 (+/-)-5,7-dioxobicyclo<2.2.2>octane-2,3-dicarboxylic acid 
• 123-31-9 hydroquinone 

Downstream Products

• 500-24-3 barrelene 
• 71-43-2 benzene 

Relevant articles and documents

Epoxidation of Barrelene: Preparation and Properties of Oxahomobarrelenes

A four-step synthesis makes barrelene (1) readily accessible on a 1-2 g scale.Upon epoxidation with KHCO3-buffered m-chloroperbenzoic acid 1 yields the mono- (2b), both the endo,exo- and exo,exo-isomeric bis- (3b and 4b) as well as the trisepoxide 5b.In the presence of traces of acid 2b very rapidly rearranges to cycloheptatriene-7-carbaldehyde (15), 5b undergoes a facile acid-catalyzed rearrangement to 4,7,11-trioxatrishomocubane (16).Under basic and neutral conditions 5b is stable towards virtually any nucleophile, its three epoxide rings can only be opened underreductive conditions with solvated electrons.On the other hand, endo,exo-dioxadihydrobishomobarrelene 20 and oxatrishomobarrelene 23 are readily attacked at the oxirane rings by lithium iodide/disodium hydrogen phosphate.