Perfluoroisobutene

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Perfluoroisobutene
IUPAC name 1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene
Other names Perfluoroisobutene, Perfluoroisobutylene, Octafluoroisobutylene, Octafluoro-sec-butene, PFIB
Identifiers
CAS number [382-21-8]
PubChem 61109
RTECS number UD1800000
SMILES C(=C(F)F)(C(F)(F)F)C(F)(F)F
InChI 1/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12
Properties
Molecular formula C4F8
Molar mass 200.030 g/mol
Density 8.2 g/l
Boiling point

7.0 °C (280 K)

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Perfluoroisobutene (PFIB), also known as 1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene, is a fluorinated olefine. 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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