83168-67-6

Basic information

• Product Name: (E,E)-(CF3CF=CF)2
• Synonyms: (E,E)-(CF3CF=CF)2
• CAS NO: 83168-67-6
• Molecular Formula: C6F10
• Molecular Weight: 262.048232
• Mol File: 83168-67-6.mol

Chemical Properties

• Boiling Point: 102.5°Cat760mmHg
• Flash Point: 17.1°C
• Appearance: /
• Density: 1.554g/cm³
• Vapor Pressure: 38.8mmHg at 25°C
• Refractive Index: 1.293
• CAS DataBase Reference: (E,E)-(CF3CF=CF)2(CAS DataBase Reference)
• NIST Chemistry Reference: (E,E)-(CF3CF=CF)2(83168-67-6)
• EPA Substance Registry System: (E,E)-(CF3CF=CF)2(83168-67-6)

Safety Data

• Hazardous Substances Data: 83168-67-6(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
(E,E)-(CF3CF=CF)2 is used as a key component in the manufacturing of fluorinated polymers for its high thermal and chemical stability, which are essential properties for various electronic applications.
Used in Automotive Industry:
In the automotive sector, (E,E)-(CF3CF=CF)2 is utilized as a building block for specialty chemicals that contribute to the development of materials with enhanced performance characteristics, such as resistance to wear and high-temperature tolerance.
Used in Aerospace Industry:
The aerospace industry benefits from (E,E)-(CF3CF=CF)2 as it is used in the creation of materials with exceptional strength and stability, which are crucial for components that operate under extreme conditions.
Used in the Development of New Materials and Technologies:
Due to its unique chemical and physical properties, (E,E)-(CF3CF=CF)2 is also valuable in the research and development of innovative materials and technologies across various industries.

InChI:InChI=1/C6F10/c7-1(3(9)5(11,12)13)2(8)4(10)6(14,15)16/b3-1+,4-2+

Upstream product

• 356-35-4 Perfluoro-1,5-hexadiene 
• 102682-82-6 (Z)-pentafluoro-1-iodo-1-propene 
• 102682-88-2 perfluoropropenylcopper 
• 89031-88-9 trans-perfluoro-3,4-dimethylcyclobutene 
• 431-65-2 perfluoroallyl iodide 
• 85131-87-9 3-Chloro-1,1,2,3,4,4,5,6,6-nonafluoro-1,5-hexadiene 

Relevant articles and documents

Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl

Adducts of primary F-alkyl iodides with nickel carbonyl are formed readily in donor solvents and pyrolyze at 100-150 °C to give olefinic coupling products in high yield. The mechanism proposed to account for the observed chemistry involves preferential α-elimination of fluorine with formation of a carbenoid species complex coordinated to nickel. Differences in reaction paths among several types of substrate halides are rationalized on the basis of polarization of the Ni-C bond in the adducts. Support for these proposals is provided by state-of-the-art calculations.

Kinetic and Thermodynamic Studies of the Thermal Electrocyclic Interconversions of Perfluorinated Dienes and Cyclobutenes

Detailed kinetic and thermodynamic analyses were carried out for the thermal interconversions of (Z,Z)- and (E,E)-perfluoro-2,4-hexadienes with trans-perfluoro-3,4-dimethylcyclobutene, (E,Z)-perfluoro-2,4-hexadiene with perfluoro-cis-3,4-dimethylcyclobutene, (Z,Z)- and (E,E)-perfluoro-3,5-octadienes with trans-perfluoro-3,4-diethylcyclobutene, and (Z)- and (E)-perfluoro-1,3-pentadiene with perfluoro-3-methylcyclobutene.In each case the (Z,Z)- or (Z)-dienes exhibited substantial kinetic advantage over the (E,E)-or (E)-dienes in their cyclization precesses.

REACTION OF 3-CHLORONONAFLUORO-1,5-HEXADIENE WITH SODIUM CYANIDE

3-Chlorononafluoro-1,5-hexadiene (I) is isomerized into 6-chlorononafluoro-1,4-hexadiene (II) by action of basic catalysts as sodium cyanide in anhydrous dimethylformamide, lithium chloride in dimethylformamide, and triethylamine in dioxane or dimethylformamide.Sodium cyanide also catalyzes addition of methanol to the chlorodiene I.The reaction course is more complex than in the alkoxide-catalyzed addition of primary alcohols to I. 6-Methoxynonafluoro-1,4-hexadiene (III), methyl perfluoro-3,6-heptadienoate (VII), and 3,6-dimethoxy-1,1,2,3,4,4,5,6,6-nonafluoro-1-hexene (VIII) have been isolated besides the known products 1,6-dimethoxy-1,1,2,3,4,5,6,6-octafluoro-2,4-hexadiene (IV) and 1,6-dimethoxy-1,1,2,3,4,4,5,6,6-nonafluoro-2-hexene (V).The hexene VIII reacts with sodium methoxide in methanol to give the diether V, and with lithium chloride in dimethylformamide it gives 1-chloro-6-methoxy-1,1,2,3,4,4,5,6,6-nonafluoro-2-hexene (IX).Stereospecificity and mechanism of the reaction are discussed.