1516-64-9

Basic information

• Product Name: (E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene
• Synonyms: (E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene;(E)-1,1,1,2,3,4,4,4-Octafluoro-2-butene
• CAS NO: 1516-64-9
• Molecular Formula: C₄F₈
• Molecular Weight: 200.0300256
• EINECS: 216-168-5
• Mol File: 1516-64-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 8.3°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.521g/cm³
• Vapor Pressure: 1360mmHg at 25°C
• Refractive Index: 1.26
• CAS DataBase Reference: (E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene(1516-64-9)
• EPA Substance Registry System: (E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene(1516-64-9)

Safety Data

• Hazardous Substances Data: 1516-64-9(Hazardous Substances Data)

Usage

Description

(E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene, with the molecular formula C4F8, is a colorless and odorless chemical compound. It is recognized for its high thermal stability, chemical resistance, and low friction properties, which contribute to its value in the production of fluoropolymers. These fluoropolymers are utilized in a range of applications, including non-stick coatings, insulating materials, and chemical resistance linings. Despite its usefulness, care must be taken in handling this compound due to potential environmental and health risks.

Uses

Used in Chemical Industry:
(E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene is used as a key component in the production of fluoropolymers for its high thermal stability, chemical resistance, and low friction properties.
Used in Manufacturing of Non-stick Coatings:
(E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene is used as a base material for non-stick coatings in cookware and other industrial applications due to its low friction properties and resistance to chemical degradation.
Used in Insulating Materials:
(E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene is used as an insulating material in the electrical and electronics industry, benefiting from its thermal stability and resistance to chemical reactions that could compromise the integrity of the insulation.
Used in Chemical Resistance Linings:
(E)-1,1,1,2,3,4,4,4-octafluorobut-2-ene is used in the creation of chemical resistance linings for equipment and structures that need to withstand harsh chemical environments, capitalizing on its robust chemical resistance.

InChI:InChI=1/C4F8/c5-1(3(7,8)9)2(6)4(10,11)12/b2-1-

Upstream product

• 375-51-9 1,1,1,2,2,3,4,4,4-nonafluoro-3-iodo-butane 
• 375-26-8 2,3-dibromo-octafluorobutane 
• 357-26-6 octafluoro-1-butene 
• 379-16-8 perfluoro(methylcyclopropane) 
• 336-23-2 nonafluoropentanoic acid; potassium salt 
• 360-89-4 octafluoro-2-butene 
• 303-04-8 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene 
• 354-89-2 (pentafluoro ethyl) trifluoro silane 
• 58734-88-6 bis(trifluoromethyl)hexafluoroisopropylphosphine 
• 1463487-28-6 C₆F₁₆Si 

Downstream Products

• 29030-86-2 trans-1,1,1,4,4,4-Hexafluor-2,3-diphenyl-2-buten 
• 1516-65-0 (Z)-perfluoro-2-butene 
• 360-89-4 octafluoro-2-butene 
• 155581-11-6 (3-allyl-)heptafluorobutan-2-one 

Relevant articles and documents

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Reactions of half-sandwich ethene complexes of rhodium(I) toward iodoperfluorocarbons: Perfluoro-alkylation or -arylation of coordinated ethene versus oxidative addition

Perfluoroalkylation or perfluoroarylation of coordinated ethene takes place when complexes [Rh(η5-Cp*)(η2-C 2H4)2] or [Rh(η5-Cp*) (η2-C2H4)(PR3)] react with IRF, to give complexes [Rh(η5-Cp*)(CH 2CH2RF)(μ-I)]2 (RF = CF(CF3)2(1a), CF(CF3)CF2CF 3 (1b), or C(CF3)3 (1c)) and [(η5-Cp*)IRh(μ-I)2Rh(η5- Cp*)(CH2CH2RF)] (2a-c), or [Rh(η5-Cp*)(CH2CH2R F)I(PR3)] (R = Me, RF = CF(CF3) 2 (3a), C(CF3)3 (3c), C6F 5 (3d); R = Ph, RF = CF(CF3)2 (3a′), CF2C6F5 (3e′)), respectively. Bridge splitting reactions of 1a, 1b, or 1c with phosphines afford complexes [Rh(η5-Cp*)(CH2CH2R F)I(PR3)] (3a, 3a′, 3c; RF = CF(CF 3)2, R = iPr (3a″); RF = CF(CF3)CF2CF3, R = Me (3b), Ph (3b′)). In contrast, oxidative addition dominates over addition to ethene in the reactions of [Rh(η5-Cp*)(η2-C2H 4)(PMe3)] with IRF (RF = CF 2C6F5, nC3F7, nC4F9, CF=CF2) and in the reaction of [Rh(η5-Cp)(η2-C2H 4)(PMe3)] with InC4F9, affording complexes of the type [Rh(η5-C5R 5)(RF)I(PMe3)] (4e-h and 5, respectively). The reaction of [Rh(η5-Cp*)(η2-C 2H4)(PR3)] with ICF(CF3)CF 2CF3 gives a mixture of cis- and trans-octafluoro-2-butene as the main fluoroorganic reaction product. Evidence for the intermediacy of RF- anions in these reactions has been obtained. 3a′ reacts with AgOTf (OTf = O3SCF3) and XyNC or CO to give complexes [Rh(η5-Cp*){CH2CH 2CF(CF3)2}(CNXy)(PPh3)]OTf (6) or [Rh(η5-Cp*){C(O)CH2CH2CF(CF 3)2}(CO)(PPh3)]OTf (7), respectively. Complex [Rh(η5-Cp*)I(py)(PMe3)]BF4 (8) was obtained either by reaction of (1) [Rh(η5-Cp*) (η2-C2H4)(PMe3)] with [I(py)2]BF4 or (2) [Rh(η5-Cp*)I 2(PMe3)] with AgBF4 and py. The crystal structures of 1a, 1b, 3c, 4g, 7, and 8 have been determined.

Solvents for use in fluorination reactions

A method of fluorinating an organic compound comprising reacting an organic compound with a fluorinating agent characterized in that a perfluorocarbon compound is present in the reaction medium. The perfluorocarbon compound may replace an amount of a solvent which would otherwise be required for the reaction to proceed efficiently. The perfluorocarbon compound is readily recoverable after reaction and may be re-used in subsequent reactions. Additives to the reaction medium, such as 18-crown-6, may increase the amoun of solvent which may be replaced. The method is beneficial where solvent consumption would otherwise be large, or where solvent recovery would otherwise be difficult.