355-75-9

Basic information

• Product Name: DECAFLUOROCYCLOHEXENE
• Synonyms: DECAFLUOROCYCLOHEXENE;PERFLUOROCYCLOHEXENE;Cyclohexene, decafluoro-;decafluoro-cyclohexen;1,2,3,3,4,4,5,5,6,6-Decafluoro-1-cyclohexene;1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene
• CAS NO: 355-75-9
• Molecular Formula: C₆F₁₀
• Molecular Weight: 262.05
• EINECS: 206-592-9
• Mol File: 355-75-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: -50°C
• Boiling Point: 53°C
• Appearance: /
• Density: 1.6650
• Vapor Pressure: 170mmHg at 25°C
• Refractive Index: 1.2930
• CAS DataBase Reference: DECAFLUOROCYCLOHEXENE(CAS DataBase Reference)
• NIST Chemistry Reference: DECAFLUOROCYCLOHEXENE(355-75-9)
• EPA Substance Registry System: DECAFLUOROCYCLOHEXENE(355-75-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 355-75-9(Hazardous Substances Data)

Usage

General Description

Decafluorocyclohexene, also known as perfluorodecahydronaphthalene, is a fluorocarbon compound with the molecular formula C6F10. It is a stable, colorless liquid at room temperature and has a high boiling point. Decafluorocyclohexene is a highly fluorinated chemical that is utilized in various industrial applications, including as a refrigerant, solvent, and as a precursor to produce other fluorinated compounds. It is also used as a substitute for ozone-depleting substances and as a fluid for heat transfer in cooling systems. However, it is important to handle decfluorocyclohexene with care as it is considered a potential environmental hazard due to its ozone-depleting properties.

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

Upstream product

• 308-24-7 undecafluorocyclohexane 
• 374-88-9 1,2,2,3,3,4,4,5,5,6,6-perfluorocyclohexanecarboxylic acid 
• 91-22-5 quinoline 
• 392-56-3 Hexafluorobenzene 
• 57113-75-4 4-bromononafluorocyclohexene 
• 6588-63-2 1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexanecarbonyl fluoride 
• 775-40-6 1H,2H-octafluorocyclohex-1-ene 
• 15145-21-8 1-chloro-2,3,3,4,4,5,5,6,6-nonafluorocyclohexene 
• 377-70-8 perfluoro-1,3-cyclohexadiene 
• 336-15-2 chloro-undecafluoro-cyclohexane 
• 355-69-1 iodoundecafluorocyclohexane 
• 336-14-1 1,2-dichlorodecafluorocyclohexane 
• 830-49-9 difluoro (pentafluorophenyl)borane 
• 260405-66-1 pentafluorophenyldifluoroxenonium(IV) tetrafluoroborate 

Downstream Products

• 2356-01-6 Nonafluor-1-<2'.2'.2'-trifluor-ethoxy>-cyclohexen 
• 6156-66-7 Nonafluor-3-<2'.2'.2'-trifluor-ethoxy>-cyclohexen 
• 4943-16-2 <2,2,2-Trifluor-ethyl>-undecafluorcyclohexyl-ether 
• 4943-13-9 <1,2,2,2-Tetrafluor-ethyl>-undecafluorcyclohexyl-ether 
• 4943-12-8 Perfluoro(cyclohexyl ethyl ether) 
• 6146-01-6 Nonafluor-1-<2'.2'.3'.3'-tetrafluor-propoxy>-cyclohexen 
• 6156-67-8 Nonafluor-3-(2',2',3',3'-tetrafluor-propoxy)-cyclohexen 
• 7523-36-6 2,H-Decafluor cyclohexyl methanol 
• 74693-95-1 Perfluoro-1-isopropylcyclohexene 
• 49851-76-5 perfluoprobicyclopentylidene 
• 26114-19-2 Eicosafluoro-1-cyclohexylcyclohexen 
• 74693-93-9 perfluorocyclohexylcyclopentene 
• 951-78-0 2'-deoxyuridine 
• 83107-65-7 deoxy-5-(peerfluorocyclohexen-1-yl)uridine 

Relevant articles and documents

Perfluoroalkylation of Alkenes by Frustrated Lewis Pairs

The activation of perfluoroalkyl iodides by the frustrated Lewis pair tris(pentafluorophenyl)borane and tri-tert-butylphosphine is described. By abstraction of both a fluorine and an iodine atom, an iodophosphonium fluoroborate salt is formed. In the presence of alkenes the corresponding iodoperfluoroalkylation products are generated regioselectively. First mechanistic investigations support a radical mechanism.

Explored routes to unknown polyfluoroorganyliodine hexafluorides, R FIF6

Two routes to RFIF6 compounds were investigated: (a) the substitution of F by RF in IF7 and (b) the fluorine addition to iodine in RFIF4 precursors. For route (a) the reagents C6F5SiMe3, C6F 5SiF3, [NMe4][C6F 5SiF4], C6F5BF2, and 1,4-C6F4(BF2)2 were tested. C 6F5IF4 and CF3CH2IF 4 were used in route (b) and treated with the fluoro-oxidizers IF7, [O2][SbF6]/KF, and K2[NiF 6]/KF. The observed sidestep reactions in case of routes (a) and (b) are discussed. Interaction of C6F5SiX3 (X = Me, F), C6F5BF2, 1,4-C6F 4(BF2)2 with IF7 gave exclusively the corresponding ring fluorination products, perfluorinated cyclohexadiene and cyclohexene derivatives, whereas [NMe4][C6F 5SiF4] and IF7 formed mixtures of C 6FnIF4 and C6FnH compounds (n = 7 and 9). CF3CH2IF4 was not reactive towards the fluoro-oxidizer IF7, whereas C6F 5IF4 formed C6FnIF4 compounds (n = 7 and 9). C6F5IF4 and CF 3CH2IF4 were inert towards [O 2][SbF6] in anhydrous HF. CF3CH 2IF4 underwent C-H fluorination and C-I bond cleavage when treated with K2[NiF6]/KF in HF. The fluorine addition property of IF7 was independently demonstrated in case of perfluorohexenes. C4F9CFCF2 and IF7 underwent oxidative fluorine addition at -30 °C, and the isomers (CF 3)2CFCFCFCF3 (cis and trans) formed very slowly perfluoroisohexanes even at 25 °C. The compatibility of IF7 and selected organic solvents was investigated. The polyfluoroalkanes CF 3CH2CHF2 (PFP), CF3CH 2CF2CH3 (PFB), and C4F9Br are inert towards iodine heptafluoride at 25 °C while CF3CH 2Br was slowly converted to CF3CH2F. Especially PFP and PFB are new suitable organic solvents for IF7.