5,6,11,12,17,18-hexadehydrotribenzo[a,e,i][12]annulene

Base Information

• Chemical Name: 5,6,11,12,17,18-hexadehydrotribenzo[a,e,i][12]annulene
• CAS No.: 5385-26-2
• Molecular Formula: C24H12
• Molecular Weight: 300.359
• Mol file: 5385-26-2.mol

Synonyms:Tribenzo[a,e,i]cyclododecene,5,6,11,12,17,18-hexadehydro;

Chemical Property of 5,6,11,12,17,18-hexadehydrotribenzo[a,e,i][12]annulene

Chemical Property:

• Vapor Pressure: 1.49E-10mmHg at 25°C
• Melting Point: 219.0-220.5 °C
• Boiling Point: 524.1°Cat760mmHg
• Flash Point: 267.5°C
• PSA: 0.00000
• Density: 1.26g/cm³
• LogP: 4.19940

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5,6,11,12,17,18-hexadehydrotribenzo[a,e,i][12]annulene

There total 3 articles about 5,6,11,12,17,18-hexadehydrotribenzo[a,e,i][12]annulene 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: 33.0%

2-bromo-1-ethynylbenzene (766-46-1) → tribenzohexahydro[12]annulene (5385-26-2) + 1,4-bis(2-bromophenyl)-1,3-butadiyne (107793-04-4)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride;

DOI:10.1055/s-2004-822393

Reference yield:

nickel(O) tribenzocyclyne (98779-78-3) + carbon monoxide (201230-82-2) → tribenzohexahydro[12]annulene (5385-26-2) + tetracarbonyl nickel (13463-39-3,71564-36-8)

Guidance literature:

In diethyl ether; dissolving of Ni(TBC) in Et2O, bubbling of CO gas through the soln., color change to clear yellow;

Reference yield:

nickel(O) tribenzocyclyne (98779-78-3) + iodine (7553-56-2,12190-71-5,8031-47-8) → nickel(II) iodide (13462-90-3) + tribenzohexahydro[12]annulene (5385-26-2)

Guidance literature:

In neat (no solvent); a. grinding of Ni(TBC) in a mortar with I2 under Ar, repeated addn. of seeral drops of Et2O; b. diffusion of I2 vapor into a flask containing Ni(TBC) (4 d);

upstream raw materials:

2-bromo-1-ethynylbenzene

nickel(O) tribenzocyclyne

iodine

carbon monoxide

Downstream raw materials:

Cu₃(O₃SCF₃)3(1,2:5,6:9,10-tribenzocyclododeca-1,5,9-triene-3,7,11-triyne)*C₆H₆

Cu(O₃SCF₃)(1,2:5,6:9,10-tribenzocyclododeca-1,5,9-triene-3,7,11-triyne)

Refernces

• 1、 Ferrara,Tanaka,Fierro,Tessier-Youngs,Youngs. "Synthesis and structural and theoretical characterization of a nickel(0) complex of tribenzocyclyne (TBC) and the preparation of a novel organometallic conductor". . p. 2089 - 2098. Retrieved 2008/10/08.