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
UNII	1J9BGS6NTY^Y
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.

External links

• International Chemical Safety Card 1216