[2.2]Orthocyclophane

Base Information

• Chemical Name: [2.2]Orthocyclophane
• CAS No.: 1460-59-9
• Molecular Formula: C16H16
• Molecular Weight: 208.303
• Mol file: 1460-59-9.mol

Synonyms:1,2:5,6-Dibenzocyclooctane;5,6,11,12-Tetrahydrodibenzo[a,e]cyclooctene; Cyclodi-o-xylylene;Dibenzocycloocta-1,5-diene; NSC 206242; [2.2]Orthocyclophane;s-Dibenzocyclooctadiene

Chemical Property of [2.2]Orthocyclophane

Chemical Property:

• Vapor Pressure: 0.00121mmHg at 25°C
• Boiling Point: 308.8°Cat760mmHg
• Flash Point: 144.8°C
• PSA: 0.00000
• Density: 1.033g/cm³
• LogP: 3.57040

Purity/Quality:

98% ^*data from raw suppliers

5,6,11,12-Tetrahydrodibenzo[a,e][8]annulene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [2.2]Orthocyclophane

There total 57 articles about [2.2]Orthocyclophane 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: 98.0%

bis(triphenylphosphine)ethylenenickel(0) (23777-40-4) + α,α'-dibromo-o-xylene (91-13-4) → dibromobis(triphenylphosphine)nickel(II) (36673-36-6,111408-20-9,14126-37-5,54053-52-0) + 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene (1460-59-9)

Guidance literature:

In diethyl ether; under Ar, into stirred soln. of C6H4(CH2Br)2 in ether Ni complex introduced at -20°C over 1 h;

DOI:10.1016/S0022-328X(00)83863-2

Reference yield: 91.0%

dibenzo[a,e]cyclooctatetraene (1032936-97-2,223682-16-4,223682-17-5,262-89-5) → 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene (1460-59-9)

Guidance literature:

With [Fe₃(1,1,1,3,3,3-hexamethyldisilazan-2-ide)₄]Fe(η⁶-toluene); hydrogen; at 20 ℃; for 3h; under 1425.14 Torr; chemoselective reaction; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201612548

Reference yield: 80.0%

α,α'-dibromo-o-xylene (91-13-4) → 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene (1460-59-9)

Guidance literature:

With lithium; for 1h; Irradiation;

DOI:10.1021/jo00364a040

upstream raw materials:

1,3-dihydrobenzo[c]thiophene-2,2-dioxide

dibenzo[a,e]cyclooctatetraene

5,6-dihydro-dibenzocyclooctene

α,α'-dibromo-o-xylene

Downstream raw materials:

anthracene

Dibenzocycloocten-5,6-dion

5-oxo-5,6-dihydrodibenzocyclooctene

5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctadiene

Refernces

• 1、 Wong,H.N.C. et al.. "-". . p. 5604 - 5605. Retrieved 1974.
• 2、 Han, Byung Hee,Boudjouk, Philip. "Organic Sonochemistry. Ultrasound-Promoted Reaction of Zinc with α,α'-Dibromo-o-xylene. Evidence for Facile Generation of o-Xylylene". . p. 751 - 752. Retrieved 1982.
• 3、 Zenouz, A. Moshtaghi. "Synthesis of some substituted 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene derivatives through the intermediacy of tricarbonyl(η6 -arene)chromium complexes". . p. 2967 - 2971. Retrieved 2004.
• 4、 Errede. "". . . Retrieved 1961.
• 5、 Errede,L.A.. "-". . p. 2606 - 2608. Retrieved 1961.
• 6、 Shirakawa, Hidenori,Sano, Hiroshi. "2-[(Trimethylsilyl)methyl]benzyl methanesulfonates: Useful precursors for the generation of o -quinodimethanes". . p. 1788 - 1792. Retrieved 2014.
• 7、 Kuwano, Ryoichi,Shige, Takenori. "Potassium fluoride-induced 1,4-elimination of o-[(trimethylsilyl)methyl] benzyl acetates: A versatile generation of o-quinodimethanes". . p. 728 - 729. Retrieved 2005.
• 8、 -. "Crosslinked Polymers with Tunable Coefficients of Thermal Expansion". Paragraph 0012; 0025. . Retrieved 2021/12/30.
• 9、 -. "Photo-catalytic preparation method of bibenzyl compounds". Paragraph 0072-0075; 0072-0075; 0078. . Retrieved 2020/02/27.