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Perfluoroisobutene

Perfluoroisobutene (PFIB) is the perfluorocarbon counterpart of the hydrocarbon isobutene and has the formula (CF3)2C=CF2. A fluoroalkene, it is a colorless gas that is notable as a highly toxic perfluoroalkene. Few simple alkenes are as toxic.

Perfluoroisobutene
Names
Preferred IUPAC name
1,1,3,3,3-Pentafluoro-2-(trifluoromethyl)prop-1-ene
Other names
Perfluoroisobutene, Perfluoroisobutylene, Octafluoroisobutylene, Octafluoro-sec-butene, PFIB
Identifiers
  • 382-21-8 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL4634291
ChemSpider
  • 55060 Y
ECHA InfoCard 100.108.743
EC Number
  • 609-533-9
  • 61109
RTECS number
  • UD1800000
UNII
  • 1J9BGS6NTY Y
  • DTXSID4073176
  • 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
  • C(=C(F)F)(C(F)(F)F)C(F)(F)F
Properties
C4F8
Molar mass 200.030 g/mol
Appearance colorless gas
Density 8.2 g/l
Melting point −130 °C (−202 °F; 143 K)
Boiling point 7.0 °C (44.6 °F; 280.1 K)
Hazards
GHS labelling:
Danger
H330, H370
P260, P264, P270, P271, P284, P304+P340, P307+P311, P310, P320, P321, P403+P233, P405, P501
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 ?)

Safety edit

Perfluoroisobutene is highly toxic with an LCt = 880 mg⋅min⋅m−3 (mice).[1] It is a Schedule 2 substance of the Chemical Weapons Convention.

Perfluoroisobutene is highly reactive toward nucleophiles. It hydrolyzes readily to give the relatively innocuous (CF3)2CHCO2H, which readily decarboxylates to give hexafluoropropane. It forms addition compounds with thiols, and it is this reactivity that may be related to its toxicity.[1]

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

See also edit

References edit

  1. ^ a b Timperley, Christopher M. (2000). "Highly-toxic fluorine compounds". Fluorine Chemistry at the Millennium. pp. 499–538. doi:10.1016/B978-008043405-6/50040-2. ISBN 9780080434056.

External links edit

  • International Chemical Safety Card 1216

perfluoroisobutene, this, article, needs, additional, citations, verification, please, help, improve, this, article, adding, citations, reliable, sources, unsourced, material, challenged, removed, find, sources, news, newspapers, books, scholar, jstor, decembe. This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Perfluoroisobutene news newspapers books scholar JSTOR December 2022 Learn how and when to remove this message Perfluoroisobutene PFIB is the perfluorocarbon counterpart of the hydrocarbon isobutene and has the formula CF3 2C CF2 A fluoroalkene it is a colorless gas that is notable as a highly toxic perfluoroalkene Few simple alkenes are as toxic Perfluoroisobutene Names Preferred 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 ChEMBL ChEMBL4634291 ChemSpider 55060 Y 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 NKey DAFIBNSJXIGBQB UHFFFAOYSA N NInChI 1 C4F8 c5 2 6 1 3 7 8 9 4 10 11 12Key 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 Appearance colorless gas Density 8 2 g l Melting point 130 C 202 F 143 K Boiling point 7 0 C 44 6 F 280 1 K Hazards GHS labelling Pictograms Signal word Danger Hazard statements H330 H370 Precautionary statements P260 P264 P270 P271 P284 P304 P340 P307 P311 P310 P320 P321 P403 P233 P405 P501 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Safety 2 See also 3 References 4 External linksSafety editPerfluoroisobutene is highly toxic with an LCt 880 mg min m 3 mice 1 It is a Schedule 2 substance of the Chemical Weapons Convention Perfluoroisobutene is highly reactive toward nucleophiles It hydrolyzes readily to give the relatively innocuous CF3 2CHCO2H which readily decarboxylates to give hexafluoropropane It forms addition compounds with thiols and it is this reactivity that may be related to its toxicity 1 PFIB is a product of pyrolysis of polytetrafluoroethylene PTFE one of the substances invoked to explain polymer fume fever See also editPhosgene Bis trifluoromethyl disulfideReferences edit a b Timperley Christopher M 2000 Highly toxic fluorine compounds Fluorine Chemistry at the Millennium pp 499 538 doi 10 1016 B978 008043405 6 50040 2 ISBN 9780080434056 External links editInternational Chemical Safety Card 1216 Retrieved from https en wikipedia org w index php title Perfluoroisobutene amp oldid 1176281166, wikipedia, wiki, book, books, library,

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