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Usage

Uses

Used in Electronics Industry:
Octafluoro-1,3,5-hexatriene is used as a specialty gas for its unique electrical properties, which make it valuable in certain applications within the electronics industry. Its conjugated carbon-fluorine bonds provide distinct characteristics that can be harnessed for specific electronic components or processes.
Used in Chemical Research:
In the field of chemical research, Octafluoro-1,3,5-hexatriene serves as a model compound for studying the effects of fluorination on the reactivity and stability of unsaturated hydrocarbons. Its conjugated structure allows researchers to explore the influence of fluorine atoms on the electronic properties and reactivity of the molecule, which can lead to the development of new materials and compounds with tailored properties.
Used in Material Science:
Octafluoro-1,3,5-hexatriene is used as a precursor in the synthesis of advanced materials, particularly those with potential applications in high-performance plastics, coatings, and adhesives. Its unique combination of stability and reactivity can contribute to the development of new materials with improved properties, such as increased resistance to heat, chemicals, or wear.
Safety Considerations:
Due to the potential release of harmful or hazardous fluoro-organic compounds upon decomposition, Octafluoro-1,3,5-hexatriene requires careful handling and storage to minimize risks. Proper safety measures, including the use of protective equipment and containment systems, are essential to ensure the safe use of Octafluoro-1,3,5-hexatriene in various applications.

Upstream product

• 307-25-5 1,2,3,4,5,6-hexachloro-octafluoro-hexane 
• 85131-86-8 1,6-Dibromo-2,3,5-trichloro-1,1,2,3,4,4,5,6,6-nonafluorohexane 
• 359-37-5 Iodotrifluoroethylene 
• 293302-61-1 (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] 

Downstream Products

• 104330-35-0 1,6-Dimethoxy-1,1,2,3,4,5,6,6-octafluoro-3-hexene 

Relevant academic research and scientific papers

The stereoselective synthesis of (E)-octafluoro-1,3,5-hexatriene and (3E,5E,7E)-dodecafluoro-1,3,5,7,9-decapentaene

(E)-(1,2-Difluoro-1,2-ethenediyl)bis[tributylstannane], 3, readily undergoes a Pd(PPh3)4/CuI-catalyzed cross-coupling reaction with iodotrifluoroethene to yield (E)-octafluoro-1,3,5-hexatriene, 4, in high isomeric purity. (1Z,3E,5Z)-

The Perfluoro-1,3,5-hexatrienes

trans-Perfluoro-1,3,5-hexatriene was obtained by catalytic isomerization of the cis isomer, and their configurations were confirmed by a photochemical method.Equilibration of these isomers with iodine and light at 13 deg C revealed that the cis isomer is slightly more stable than the trans (Kc-t = 0.83).The trienes undergo reactions under the influence of heat and light which contrast with those of their hydrocarbon counterparts.Cis triene cyclizes reversibly to perfluoro-3-vinylcyclobutene at 160 deg C (Keq = 12.2), and at higher temperatures perfluoro-1,3-cyclohexadiene is formed irreversibly.Cyclization of trans triene to the vinylcyclobutene is much slower than that of the cis isomer, as required by the finding that thermal ring opening of the vinylcyclobutene gives cis triene cleanly.Ultraviolet irradiation of the trienes with and without mercury sensitization yields the same two cyclization products, but the cyclohexadiene undergoes a further rapid photocyclization to give perfluorobicyclohex-2-ene, as reported recently by Dedek's group.Mercury photosensitization of the vinylcyclobutene proceeds smoothly to yield this same bicyclic olefin.

Thermal and UV-induced isomerisation of fluorinated hexatrienes

Irradiation of octafluoro-1,3,5-hexatriene (I) in the gas phase with a high-pressure mercury lamp gave a mixture of octafluoro-2-vinyl-cyclobutene (III) and octafluorobicyclohex-2-ene (V).The analogous photolysis of hexatriene I in the liquid phase led to an equilibrium mixture of the starting compound I (cis-isomer) and the trans-isomer II, respectively.Photolysis of 2,3,4,5-tetrafluro-1,3,5-hexatriene (VI) gave a mixture of cis- and trans-isomers, both in the vapour and liquid phases.Thermal reaction of hexatriene I gave octafluoro-1,3-cyclohexadiene (IV) as the sole product.

ADDITION OF 1,2-DIBROMO-1-CHLOROTRIFLUOROETHANE TO CHLOROTRIFLUOROETHYLENE INDUCED BY UV-RADIATION. SYNTHESIS OF PERFLUORO-1,3-BUTADIENE AND PERFLUORO-1,3,5-HEXATRIENE

Photochemically initiated reaction of 1,2-dibromo-1-chlorotrifluoroethane (II) with chlorotrifluoroethylene (I) gave 38percent 1,4-dibromo-2,3-dichlorohexafluorobutane (III) and 19percent 1,6-dibromo-2,3,5-trichlorononafluorohexane (IV) in addition to the higher telomers.Dehalogenations of III and IV yielded perfluoro-1,3-butadiene (VI) and perfluoro-1,3,5-hexatriene (VIII) with 3-chlorononafluoro-1,5-hexadiene (VII), respectively.Photochemical reduction of butane III with 2-propanol resulted in a preferential reduction of C-Br bonds, and from 2,3-dichloro-1,1,2,3,4,4-hexafluorobutane (IX) thus formed, esters of difluoroacetic acid were prepared by dehalogenation of IX and subsequent oxidation and esterification of the product.The photochemical reduction of hexane IV gave a mixture of 79percent trichlorononafluorohexane XII and 21percent dichlorononafluorohexane XIII.The mechanism of formation of the unusual products of the title addition reaction is discussed.

ADDITION OF PRIMARY ALCOHOLS TO 3-CHLORONONAFLUORO-1,5-HEXADIENE AND PERFLUORO-1,3,5-HEXATRIENE

Sodium alkoxide-catalyzed addition of methanol, ethanol and propanol to 3-chlorononafluoro-1,5-hexadiene (I) proceeds at temperatures -35 deg C to 8 deg C with allyl rearrangement, affording 1,6-dialkoxy-1,1,2,3,4,4,5,6,6-octafluoro-2,4-hexadiene (V) as the principal product, along with 1,6-dialkoxy-1,2,3,3,4,5,6,6-octafluoro-1,5-diene (VI) and trans-1,6-dialkoxy-1,1,2,3,4,4,5,6,6-nonafluoro-2-hexene (VII).The ethers Va-Vc consist of the cis,trans- and trans,trans-isomers in about 3:1 ratio, whereas the ethers VIa-VIc have trans,trans-configuration.Ethers Vc and VIc react with concentrated sulfuric acid to give dipropyl 2,3,4,5-tetrafluoro-2,4-hexadienedioate (IX) and dipropyl 2,3,4,4,5-pentafluoro-2-hexenedioate (X), respectively, whereas the ether VIIc affords a mixture of propyl 6-propyloxy-2,3,4,4,5,6-heptafluoro-2-hexenoate (XI) and ester X.Addition of methanol to perfluoro-1,3,5-hexatriene (II) affords 1,1,2,3,4,5,6,6-octafluoro-1,6-dimethoxy-3-hexene (XIII) as the principal product.