Perfluoroisobutene

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.

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
CAS Number	382-21-8 Y
3D model (JSmol)	Interactive image
ChemSpider	55060 N
ECHA InfoCard	100.108.743
EC Number	609-533-9
PubChem CID	61109
RTECS number	UD1800000
CompTox Dashboard (EPA)	DTXSID4073176
InChI InChI=1S/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12 N Key: DAFIBNSJXIGBQB-UHFFFAOYSA-N N InChI=1/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12 Key: DAFIBNSJXIGBQB-UHFFFAOYAF
SMILES C(=C(F)F)(C(F)(F)F)C(F)(F)F
Properties
Chemical formula	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).
N verify (what is YN ?)
Infobox references

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.