500-24-3

Basic information

• Product Name: Bicyclo[2.2.2]octa-2,5,7-triene
• Synonyms: Barrelene;Bicyclo[2.2.2]octa-2,5,7-triene
• CAS NO: 500-24-3
• Molecular Formula: C₈H₈
• Molecular Weight: 104.15
• Mol File: 500-24-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 153.7°C at 760 mmHg
• Flash Point: 22.3°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 4.22mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: Bicyclo[2.2.2]octa-2,5,7-triene(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.2]octa-2,5,7-triene(500-24-3)
• EPA Substance Registry System: Bicyclo[2.2.2]octa-2,5,7-triene(500-24-3)

Safety Data

• Hazardous Substances Data: 500-24-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8/c1-2-8-5-3-7(1)4-6-8/h1-8H

Upstream product

• 78323-65-6 C₁₅H₁₆N₂O₂S 
• 61543-85-9 Bicyclo<2.2.2>oct-7-en-2,5-dion-bis(tosylhydrazon) 

Downstream Products

• 61169-18-4 3-ethoxy-(4ar,8ac)-4a,5,8,8a-tetrahydro-5,8-etheno-benzo[1,3,4]oxadiazine-1-carboxylic acid ethyl ester 
• 61169-19-5 3,3a,3b,6,6a,6b-hexahydro-3,6-cyclo-cyclopropa[de]cinnoline-1,2-dicarboxylic acid diethyl ester 
• 280-33-1 bicyclo[2,2,2]octane 

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.