1763-21-9

Basic information

• Product Name: 3,3,4,4-TETRAFLUORO-1,5-HEXADIENE
• Synonyms: 3,3,4,4-TETRAFLUORO-1,5-HEXADIENE;1,2-divinylperfluoroethane;3,3,4,4-tetrafluorohexa-1,5-diene
• CAS NO: 1763-21-9
• Molecular Formula: C₆H₆F₄
• Molecular Weight: 154.11
• EINECS: 217-178-2
• Mol File: 1763-21-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 72°C
• Flash Point: 0.9°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 43.6mmHg at 25°C
• Refractive Index: 1.347
• CAS DataBase Reference: 3,3,4,4-TETRAFLUORO-1,5-HEXADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,4,4-TETRAFLUORO-1,5-HEXADIENE(1763-21-9)
• EPA Substance Registry System: 3,3,4,4-TETRAFLUORO-1,5-HEXADIENE(1763-21-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1763-21-9(Hazardous Substances Data)

Usage

General Description

3,3,4,4-Tetrafluoro-1,5-hexadiene, also known as TFHD, is a colorless liquid with a molecular formula of C6H6F4. This chemical is used as a building block in the synthesis of fluorinated compounds, and its unique structure allows for a variety of reactions and applications in the field of organic chemistry. TFHD is commonly used in the production of pharmaceuticals, agrochemicals, and specialty materials. This chemical is also known for its high heat stability and low reactivity, making it a valuable ingredient in the manufacturing of high-performance polymers and materials. TFHD is also gaining attention as a potential alternative to ozone-depleting substances due to its low environmental impact. However, like all chemicals, proper handling and safety precautions should be taken when working with 3,3,4,4-Tetrafluoro-1,5-hexadiene.

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

• 35207-93-3 1-(1,1,2,2-tetrafluoro-3-buten-1-yl)-2,2,3,3-tetraflouoro-cyclobutane 
• 35207-94-4 tetrafluoro-1,2-(RS)-bis(2,2,3,3-tetrafluorocyclobutyl)ethane 
• 35208-07-2 3,3,4,4,7,7,8,8,8-Nonafluorocten-1 
• 35208-09-4 3,3,4,4,7,7,8,8,8-Nonafluor-5-jodocten-1 
• 35208-15-2 1,1,2,2-tetrafluoro-3-iodo-5-(2,2,3,3,3-pentafluoro-propyl)-cyclopentane 
• 35208-03-8 Tetrafluor-1-jodmethyl-2-pentafluorpropylcyclobutan 
• 35208-08-3 1,1,1,2,2,5,5,6,6,9,9,10,10,10-Tetradecafluor-3-decen 
• 35208-02-7 C₁₀H₆Cl₂F₁₀ 
• 35262-54-5 1.1.1.2.2.5.5.6.6-Nonafluor-octan 
• 40723-75-9 3,3,4,4,7,7,8,8,8-nonafluoro-octa-1,5-diene 
• 35278-79-6 1,1,1,2,2,5,5,6,6,9,9,10,10,10-Tetradecafluordecan 
• 35207-97-7 1,1,2,2-Tetrafluoro-3-(1,1,2,2-tetrafluoro-butyl)-cyclobutane 
• 35208-00-5 3-(3,4-Dibromo-1,1,2,2-tetrafluoro-butyl)-1,1,2,2-tetrafluoro-cyclobutane 
• 41241-69-4 5,7,7,7-tetrachloro-3,3,4,4-tetrafluoro-hept-1-ene 

Relevant articles and documents

Effect of Terminal Fluorine Substitution on the Cope Rearrangement: Boat versus Chair Transition State. Evidence for a Very Significant Fluorine Steric Effect

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[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.