1763-21-9

Usage

Uses

Used in Pharmaceutical Industry:
3,3,4,4-Tetrafluoro-1,5-hexadiene is used as a key intermediate in the synthesis of various pharmaceuticals, leveraging its fluorinated properties to enhance the stability, solubility, and bioavailability of drug molecules.
Used in Agrochemical Industry:
TFHD serves as a crucial component in the production of agrochemicals, where its unique chemical structure contributes to the development of effective and environmentally friendly pesticides and herbicides.
Used in Specialty Materials Industry:
3,3,4,4-Tetrafluoro-1,5-hexadiene is utilized as a building block for specialty materials, capitalizing on its heat stability and low reactivity to create materials with superior performance characteristics for specific applications.
Used in High-Performance Polymers:
TFHD is used as a monomer in the manufacturing of high-performance polymers, where its properties contribute to the creation of materials with enhanced mechanical strength, thermal resistance, and chemical stability.
Used as an Alternative to Ozone-Depleting Substances:
3,3,4,4-Tetrafluoro-1,5-hexadiene is gaining attention as a potential substitute for substances that deplete the ozone layer, due to its low environmental impact and its capacity to be used in the development of more sustainable chemical products.

InChI:InChI=1/C6H6F4/c1-3-5(7,8)6(9,10)4-2/h3-4H,1-2H2

Upstream product

• 679-22-1 2,5-diacetoxy-3,3,4,4-tetrafluorohexane 
• 2163-06-6 3,3,4,4-tetrafluoro-1,6-diiodo-hexane 
• 679-11-8 3,3,4,4-tetrafluoro-hexane-2,5-diol 
• 4459-68-1 3,3,4,4-tetrafluoro-hexane-2,5-dione 
• 502870-48-6 1,1,6,6-tetrafluoro-1,5-hexadiene 

Downstream Products

• 648-36-2 3,3,4,4-Tetrafluor-hexan 
• 35208-00-5 3-(3,4-Dibromo-1,1,2,2-tetrafluoro-butyl)-1,1,2,2-tetrafluoro-cyclobutane 
• 35207-97-7 1,1,2,2-Tetrafluoro-3-(1,1,2,2-tetrafluoro-butyl)-cyclobutane 
• 35278-79-6 1,1,1,2,2,5,5,6,6,9,9,10,10,10-Tetradecafluordecan 
• 40723-75-9 3,3,4,4,7,7,8,8,8-nonafluoro-octa-1,5-diene 
• 35262-54-5 1.1.1.2.2.5.5.6.6-Nonafluor-octan 
• 35208-02-7 C₁₀H₆Cl₂F₁₀ 
• 35208-08-3 1,1,1,2,2,5,5,6,6,9,9,10,10,10-Tetradecafluor-3-decen 
• 35208-09-4 3,3,4,4,7,7,8,8,8-Nonafluor-5-jodocten-1 
• 35208-03-8 Tetrafluor-1-jodmethyl-2-pentafluorpropylcyclobutan 
• 35208-15-2 1,1,2,2-tetrafluoro-3-iodo-5-(2,2,3,3,3-pentafluoro-propyl)-cyclopentane 
• 35208-07-2 3,3,4,4,7,7,8,8,8-Nonafluorocten-1 
• 35207-94-4 tetrafluoro-1,2-(RS)-bis(2,2,3,3-tetrafluorocyclobutyl)ethane 
• 35207-93-3 1-(1,1,2,2-tetrafluoro-3-buten-1-yl)-2,2,3,3-tetraflouoro-cyclobutane 

Relevant academic research and scientific papers

[3,3] Sigmatropic rearrangement of some fluorinated 1,5-hexadienes

Fluorine atoms incorporated into 1,5-hexadiene molecule should influence the kinetic as well as the thermodynamic parameters of [3,3] sigmatropic rearrangement (Cope rearrangement). Within few decades is has been documented that this transformation proceeds in a concerted manner, rather than stepwise with some radical intermediates involved. Few new terminally fluorinated 1,5-hexadienes (compounds 3, 5A, 7, 9 and 5B) have been synthesized. The activation parameters of rearrangement have been determined and compared with those known for hydrocarbon analogues. While systems developing chair-like transition states (compounds 3 and 5) showed close similarity with hydrocarbon analogues (compound 1), those developing boat-like transition states (compounds 7, 9 and 5B) may proceed through radical stepwise mechanism. Computational studies of the transition states were carried out, showing that only ab initio methods (MP2 and especially DFT) can give approximate correlation with experimental data, whereas in the case of hydrocarbon analogues even simple semiempirical methods (AM1) were reliable enough to reproduce experimental results.

Synthesis of telechelic dienes from fluorinated α,ω-diiodoalkanes. Part I. Divinyl and diallyl derivatives from model I(C2F4)nI compounds

The synthesis of five fluorinated non-conjugated dienes from commercially available α,ω-diiodoperfluoroalkanes is described.Preparation of the fluorinated divinyl derivatives H2C=CH(CF2)nCH=CH2 (n = 2, 4, 6) (2,2, 2,4 and 2,6) was effected by ethylenation of these diiodinated compounds in various ways followed by dehydroiodination in ethanolic potassium hydroxide.Allyl diolefines, H2C=CHCH2(CF2)nCH2CH=CH2 (4,4 and 4,6) were produced by the α,ω-bis-telomerization of allyl acetate followed by deiodoacetoxylation in the presence of zinc.The diacetate precursors 3,4 and 3,6 of the respective diallyls 4,4 and 4,6 were obtained rather than diacetate 3,2 because of the eventual decomposition of α,ω-diiodoperfluoroethane by β-scission.These five fluorinated non-conjugated dienes have been characterized by 1H, 13C and 19F NMR spectroscopy. - Keywords:Telechelic dienes; Fluorinated vinyl dienes; Fluorinated allyl dienes; α,ω-Diiodoperfluoroalkanes; NMR spectroscopy