Bicyclo[2.2.2]octa-2,5,7-triene

Base Information

• Chemical Name: Bicyclo[2.2.2]octa-2,5,7-triene
• CAS No.: 500-24-3
• Molecular Formula: C8H8
• Molecular Weight: 104.152
• UNII: 2P5L4Z7K7I
• DSSTox Substance ID: DTXSID80198171
• Nikkaji Number: J11.799D
• Wikipedia: Barrelene
• Wikidata: Q653667
• Mol file: 500-24-3.mol

Synonyms:Barrelene;Bicyclo[2.2.2]octa-2,5,7-triene;500-24-3;Bicyclo(2.2.2)octa-2,5,7-triene;UNII-2P5L4Z7K7I;2P5L4Z7K7I;BARRELENE [MI];DTXSID80198171;Q653667

Chemical Property of Bicyclo[2.2.2]octa-2,5,7-triene

Chemical Property:

• Vapor Pressure: 4.22mmHg at 25°C
• Boiling Point: 153.7°C at 760 mmHg
• Flash Point: 22.3°C
• PSA: 0.00000
• Density: 1.012g/cm³
• LogP: 1.91460
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 104.062600255
• Heavy Atom Count: 8
• Complexity: 121

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2C=CC1C=C2

Technology Process of Bicyclo[2.2.2]octa-2,5,7-triene

There total 3 articles about Bicyclo[2.2.2]octa-2,5,7-triene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 13.0%

Bicyclo<2.2.2>oct-7-en-2,5-diylbis(O-p-tolylthionocarbonat) → barrelene (500-24-3) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

at 170 ℃; Yields of byproduct given;

Reference yield:

Bicyclo<2.2.2>oct-7-en-2,5-dion-bis(tosylhydrazon) (61543-85-9) → barrelene (500-24-3) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With methyllithium; In diethyl ether; for 4h; Yield given. Yields of byproduct given; Ambient temperature; further reagents: TMEDA, HMPA;

Reference yield:

C15H16N2O2S (78323-65-6) → barrelene (500-24-3) + tetracyclo<3.3.0.02,4.03,6>oct-7-ene (35434-64-1) + 3-methylenetetracyclo<3.2.0.02,7,04,6>heptane (38898-42-9) + 7-methylenenorbornadiene (37846-63-2)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given; 1) THF, 2 h, room temperature, 2) irradiation, 5h, -78 deg C;

DOI:10.1016/0040-4020(82)85065-5

upstream raw materials:

C₁₅H₁₆N₂O₂S

Bicyclo<2.2.2>oct-7-en-2,5-dion-bis(tosylhydrazon)

Downstream raw materials:

bicyclo[2,2,2]octane

3-ethoxy-(4ar,8ac)-4a,5,8,8a-tetrahydro-5,8-etheno-benzo[1,3,4]oxadiazine-1-carboxylic acid ethyl ester

3,3a,3b,6,6a,6b-hexahydro-3,6-cyclo-cyclopropa[de]cinnoline-1,2-dicarboxylic acid diethyl ester

Refernces

• 1、 Stapersma, J.,Rood, I. D. C.,Klumpp, G. W.. "SYNTHESIS OF TETRACYCLO2,4.03,6>OCT-7-ENE AND SOME OF ITS DERIVATIVES". . p. 191 - 199. Retrieved 2007/10/02.