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Perfluoroisobutene

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	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.

Additional recommended knowledge

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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 enema reduction. 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.

Categories: Organofluorides | Alkenes | Chemical weapons