6733-01-3

Basic information

• Product Name: Bicyclo(2.2.0)hexa-2,5-diene, 1,2,3,4,5,6-hexafluoro-
• Synonyms: Bicyclo(2.2.0)hexa-2,5-diene, 1,2,3,4,5,6-hexafluoro-
• CAS NO: 6733-01-3
• Molecular Formula: C₆F₆
• Molecular Weight: 0
• Mol File: 6733-01-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 107.9°C at 760 mmHg
• Flash Point: 21.5°C
• Appearance: /
• Density: 1.7g/cm³
• Vapor Pressure: 31mmHg at 25°C
• Refractive Index: 1.382
• CAS DataBase Reference: Bicyclo(2.2.0)hexa-2,5-diene, 1,2,3,4,5,6-hexafluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo(2.2.0)hexa-2,5-diene, 1,2,3,4,5,6-hexafluoro-(6733-01-3)
• EPA Substance Registry System: Bicyclo(2.2.0)hexa-2,5-diene, 1,2,3,4,5,6-hexafluoro-(6733-01-3)

Safety Data

• Hazardous Substances Data: 6733-01-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C6F6/c7-1-2(8)6(12)4(10)3(9)5(1,6)11

Upstream product

• 392-56-3 Hexafluorobenzene 

Downstream Products

• 49776-44-5 1,2,3,4,5,6-hexafluoro-9-(2,4,6-trimethyl-phenyl)-(1rH,2tH,5tH,6cH)-7-oxa-8-aza-tricyclo[4.3.0.0^2,5]nona-3,8-diene 
• 392-56-3 Hexafluorobenzene 
• 38136-27-5 2,3,5,6-tetrachlorobicyclohexane 
• 38136-55-9 exo,cis-5,6-dichlorohexafluorobicyclo<2.2.0>hex-2-ene 
• 38136-55-9 trans-5,6-dichlorohexafluorobicyclo<2.2.0>hex-2-ene 
• 74415-69-3 hexafluorocyclohexa-2,4-dien-1-one 
• 911225-20-2 1,2,4,5,6,7-hexafluoro-3-oxatricyclo[3.2.0.0^2,4]hept-6-ene 

Relevant articles and documents

Valence-bond isomer chemistry. Part 13. Photochemical oxidation of hexafluorobenzene: formation of hexafluoro-3-oxatricyclo2,4>hept-6-ene and its reactions

Vapour-phase ultraviolet irradiation of hexafluorobenzene in the presence of oxygen slowly yields hexafluoro-3-oxatricyclo2,4>hept-6-ene (2) (10percent).The CF=CF bond in 2 adds (yields of adducts given) the dienes; cyclopentadiene (74percent), furan (61percent) and 2,5-diphenylisobenzofuran (59percent); benzonitrile oxide (58percent); chlorine (59percent) and bromine (71percent) photochemically.Heptene 2 isomerises thermally hexafluorocyclohexa-2,4-dienone (6) (60percent) at 50 deg C, and reacts with diethyl ether at room temperature yielding ethyl fluoride (89percent) and 2-ethoxypentafluorocyclohexa-2,5-dienone (21percent).The benzonitrile oxide adduct, upon flow pyrolysis at 440 deg C, yields an isomeric oxepin derivative and the cyclohexadienone 6 with longer contact times.The chlorine adduct similarly yields a dichloro-oxepin derivative; attempts to dechlorinate this to hexafluoro-oxepin were unsuccessful.Benzonitrile oxide adds to one or both of the C=C bonds of hexafluorobicyclohexa-2,5-diene; the 1:1 adduct isomerises thermally to the benzonitrile oxide-hexafluorobenzene adduct.

Hexafluoro-3-oxatricyclo2,4>hept-6-ene (Hexafluoro-Dewar-benzene Oxide) from the Photochemical Oxidation of Hexafluorobenzene

Photochemical oxidation of hexafluorobenzene in the vapour phase yields the title compound, which undergoes thermal rearrangement into hexafluorocyclohexa-2,4-dienone and two acid fluorides, attack by diethyl ether at the oxiran ring, and cycloaddition to its C=C double bond.