Perfluoroisobutene

Perfluoroisobutene
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene
Other names
Perfluoroisobutene, Perfluoroisobutylene, Octafluoroisobutylene, Octafluoro-sec-butene, PFIB
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.108.743
EC Number 609-533-9
RTECS number UD1800000
Properties
C4F8
Molar mass 200.030 g/mol
Density 8.2 g/l
Boiling point 7.0 °C (44.6 °F; 280.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Perfluoroisobutene (PFIB), also known as 1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene, is a fluorocarbon alkene. It is a hydrophobic reactive gas with boiling point at 7 °C. It is a strong electrophile.

PFIB is about 10 times as toxic as phosgene. Its inhalation can lead to pulmonary edema, which may be fatal. Onset of symptoms can take 1-4 hours after inhalation. Treatment is based on management of the pulmonary edema (usually with high-dose corticoids and other medication/measures) and associated disorders (e.g. heart failure, hypocalcemia etc.). Many cases resolve within 72 hours without major long-term effects.

In contact with water PFIB undergoes rapid hydrolysis, producing various reactive compounds and fluorophosgene.

PFIB is a product of pyrolysis of polytetrafluoroethylene (PTFE), one of the substances causing polymer fume fever.

It is a Schedule 2 substance of the Chemical Weapons Convention.

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