1,3,5,7-Cyclooctatetraene

Base Information

• Chemical Name: 1,3,5,7-Cyclooctatetraene
• CAS No.: 629-20-9
• Molecular Formula: C8H8
• Molecular Weight: 104.152
• Hs Code.: 29021900
• Mol file: 629-20-9.mol

Synonyms:Cyclooctatetraene;NSC 5093;[8]Annulene;

Chemical Property of 1,3,5,7-Cyclooctatetraene

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid
• Vapor Pressure: 7.64mmHg at 25°C
• Melting Point: -5 - -3 °C(lit.)
• Refractive Index: n20/D 1.537(lit.)
• Boiling Point: 140.5 °C at 760 mmHg
• Flash Point: 22.2 °C
• PSA: 0.00000
• Density: 0.904 g/cm³
• LogP: 2.22480
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: Not miscible or difficult to mix in water.

Purity/Quality:

99.3% ^*data from raw suppliers

Cyclooctatetraene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi,T
• Statements: 10-36/37/38-65-61
• Safety Statements: 26-62-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Physical properties: Cyclooctatetraene (COT) is a poster child for nonaromatic molecules. An isomer of tub-shaped COT, with one of the ring double bonds changed from the usual cis form to a trans one, lies some 23 kcal/mol higher in energy.Cyclooctatetraene is an 8p electron system and has a triplet ground state if the p electrons are delocalized. It is antiaromatic hence highly unstable and reactive. It adopts a non-planar boat conformation to attain stability with alternating single and double bonds and hence behaves like a polyolefin.Cyclooctatetraene is a nonaromatic 4n π-conjugated system with a non-planar tub-shaped geometry and potential energy surfaces at the ground state.
• Uses: Used in the synthesis of highly organic film for silicon surfaces to improve its chemical and physical properties. 1 Used in liquid state organic dye lasers. 2 Used as triplet state quencher to reduce dye blinking. 3 1,3,5,7-Cyclooctatetraene is used in the synthesis of highly organic film for silicon surfaces to improve its chemical and physical properties. It is also used in liquid state organic dye lasers, as triplet state quencher to reduce dye blinking. COT may be functionalized by two side groups which can be used as active anode materials for rechargeable batteries. High capacity and voltage organic cathodes may be developed by using COT that can be fused with carbon molecules.

Technology Process of 1,3,5,7-Cyclooctatetraene

There total 83 articles about 1,3,5,7-Cyclooctatetraene 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: 65.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → 1,3,5,7-cyclooctatetraene (629-20-9)

Guidance literature:

1,5-cis,cis-cyclooctadiene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; pentane; for 24h;

With di-tert-butyl peroxide; In hexane; pentane; for 4h; Further stages.; Heating;

DOI:10.1016/j.tetlet.2004.03.064

Reference yield: 56.0%

(1R,7S,8R)-8-Chloro-bicyclo[5.1.0]octa-2,4-diene (69530-46-7,69576-52-9) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1,3,5,7-cyclooctatetraene (629-20-9)

Guidance literature:

With potassium tert-butylate; at 25 ℃;

DOI:10.1016/S0040-4039(01)80124-6

Reference yield: 55.0%

acetylene (74-86-2,25067-58-7) → 1,3,5,7-cyclooctatetraene (629-20-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With calcium carbide; tetrabutylammonium tetrafluoroborate; nickel; In tetrahydrofuran; at 80 ℃; for 42h; under 12751 Torr; electrolysis;

upstream raw materials:

acetylene

methanol

9-phenyl-9-phosphatricyclo<4.2.1.0^2,5>nona-3,7-diene

benzophenone

Downstream raw materials:

2,4,6-cycloheptatriene-1-carboxaldehyde dimethyl acetal

(1Z,3Z,5Z)-Cycloocta-1,3,5-triene

cycloocta-1c,3c,6c-triene

phenylacetaldehyde

Refernces

• 1、 Martin, H.-D.,Urbanek, T.,Walsh, R.. "Thermal Behavior of C8H8 Hydrocarbons. 2. Semibullvalene. Kinetic and Thermodynamic Stability". . p. 5532 - 5534. Retrieved 1985.
• 2、 Stevenson, Gerald R.,Forch, Brad E.. "Thermodynamics of Electron Transfer from the Cyclooctatetraene Anion Radical to a Series of Substituted Cyclooctatetraenes and Annulene". . p. 378 - 382. Retrieved 1981.
• 3、 Hedaya et al.. "". . p. 1875. Retrieved 1969.
• 4、 Gygax et al.. "". . p. 2567,2567,2568. Retrieved 1979.
• 5、 Majumder, Supriyo,Odom, Aaron L.. "Simple and convenient one-pot synthesis of cyclooctatetraene". . p. 1771 - 1772. Retrieved 2008.
• 6、 Felkin, Hugh,Fillebeen-Khan, Tauqir,Gault, Yvonne,Holmes-Smith, Rupert,Zakrzewski, Janusz. "ACTIVATION OF C-H BONDS IN SATURATED HYDROCARBONS. THE CATALYTIC FUNCTIONALISATION OF CYCLOOCTANE BY MEANS OF SOME SOLUBLE IRIDIUM AND RUTHENIUM POLYHYDRIDE SYSTEMS". . p. 1279 - 1282. Retrieved 1984.
• 7、 Prosen,Johnson,Rossini. "-". . p. 2068. Retrieved 1947.
• 8、 Squillacote, Michael E.,Bergman, Adelle. "Trapping of 1,3,5,7-Cyclooctatetraene Valence Tautomers. Thermodynamic Stability of Bicycloocta-2,4,7-triene". . p. 3910 - 3911. Retrieved 1986.
• 9、 Simons, Leslie H.,Lagowski. "Cyclooctatetraene dianion from 1,5-cyclooctadiene. A synthesis in the presence of naphthalene radical anion". . p. 1771 - 1773. Retrieved 2007/10/03.