| Revision as of 12:46, 18 August 2010 edit87.115.13.221 (talk)No edit summary← Previous edit | Latest revision as of 03:03, 30 November 2024 edit undo97.102.205.224 (talk) →Infobox: It's hard to make a legible SMILES out of such a bushy structure, but neaten it a little bit by starting on a leaf atom rather than the central C. (If only SMILES let us write by analogy with , it would be =C()) | ||
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| {{More citations needed|date=December 2022}} | |||
| {{chembox | {{chembox | ||
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| | verifiedrevid = 379575756 | |||
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| ⚫ | | ImageFileL1 = Perfluoroisobutene.svg | ||
| | ImageAltL1 = Skeletal formula | |||
| | ImageFileR1 = Perfluoroisobutene-3D-balls.png | |||
| | ImageAltR1 = Ball-and-stick model | |||
| ⚫ | | PIN = 1,1,3,3,3-Pentafluoro-2-(trifluoromethyl)prop-1-ene | ||
| | OtherNames = Perfluoroisobutene, Perfluoroisobutylene, Octafluoroisobutylene, Octafluoro-sec-butene, PFIB | | OtherNames = Perfluoroisobutene, Perfluoroisobutylene, Octafluoroisobutylene, Octafluoro-sec-butene, PFIB | ||
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|Section1={{Chembox Identifiers | ||
| | CASNo_Ref = {{cascite|correct|??}} | |||
| | CASNo = 382-21-8 | |||
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| CASNo = 382-21-8 | ||
| | ChEMBL = 4634291 | |||
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| | UNII_Ref = {{fdacite|correct|FDA}} | |||
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| UNII = 1J9BGS6NTY | ||
| | PubChem = 61109 | |||
| | RTECS = UD1800000 | |||
| | EINECS = 609-533-9 | |||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| | ChemSpiderID = 55060 | |||
| ⚫ | | SMILES = FC(F)=C(C(F)(F)F)C(F)(F)F | ||
| ⚫ | | InChI = 1/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12 | ||
| | InChIKey = DAFIBNSJXIGBQB-UHFFFAOYAF | |||
| | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | |||
| | StdInChI = 1S/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12 | |||
| | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | |||
| | StdInChIKey = DAFIBNSJXIGBQB-UHFFFAOYSA-N | |||
| }} | }} | ||
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|Section2={{Chembox Properties | ||
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| Formula = C<sub>4</sub>F<sub>8</sub> | ||
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| MolarMass = 200.030 g/mol | ||
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| Appearance = colorless gas | ||
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| Density = 8.2 g/l | ||
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| MeltingPtC = −130 | ||
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| BoilingPtC = 7.0 | ||
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| ⚫ | |Section3={{Chembox Hazards | ||
| | GHSPictograms = {{GHS06}}{{GHS08}} | |||
| | GHSSignalWord = Danger | |||
| | HPhrases = {{H-phrases|330|370}} | |||
| | PPhrases = {{P-phrases|260|264|270|271|284|304+340|307+311|310|320|321|403+233|405|501}} | |||
| ⚫ | | MainHazards = | ||
| ⚫ | | FlashPt = | ||
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| '''Perfluoroisobutene''' ('''PFIB''') is the ] counterpart of the hydrocarbon ] and has the formula (CF<sub>3</sub>)<sub>2</sub>C=CF<sub>2</sub>. A ], it is a colorless gas that is notable as a highly toxic ]. Few simple alkenes are as toxic. | |||
| '''Perfluoroisobutene''' ('''PFIB'''), also known as '''1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene''', is a ] ]. It is a ] reactive gas with boiling point at 7 °C. It is a strong ]. | |||
| ==Safety== | |||
| PFIB is about 10 times as toxic as ]. Its inhalation can lead to ], 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 ]s and other medication/measures) and associated disorders (e.g. ], ] etc.). Many cases resolve within 72 hours without major long-term effects. | |||
| Perfluoroisobutene is highly toxic with an LCt = 880 mg⋅min⋅m<sup>−3</sup> (mice).<ref name=Timp>{{cite book |doi=10.1016/B978-008043405-6/50040-2|chapter=Highly-toxic fluorine compounds|title=Fluorine Chemistry at the Millennium|year=2000|last1=Timperley|first1=Christopher M.|pages=499–538|isbn=9780080434056}}</ref> It is a ] substance of the ]. | |||
| Perfluoroisobutene is highly reactive toward ]s. It hydrolyzes readily to give the relatively innocuous (CF<sub>3</sub>)<sub>2</sub>CHCO<sub>2</sub>H, which readily decarboxylates to give ]. It forms addition compounds with ], and it is this reactivity that may be related to its toxicity.<ref name=Timp/> | |||
| In contact with water PFIB undergoes rapid ], producing various reactive compounds and ]. | |||
| PFIB is a product of ] of ] (PTFE), one of the substances |
PFIB is a product of ] of ] (PTFE), one of the substances invoked to explain ]. | ||
| ==See also== | |||
| It is a ] substance of the ]. | |||
| *] | |||
| *] | |||
| ==References== | |||
| {{Reflist}} | |||
| ==External links== | ==External links== | ||
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Latest revision as of 03:03, 30 November 2024
 | 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) |
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| 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 | |||
| 3D model (JSmol) | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.108.743 
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| EC Number |
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| PubChem CID | |||
| RTECS number |
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| UNII | |||
| CompTox Dashboard (EPA) | |||
InChI
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SMILES
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| 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 |  
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| 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 , 100 kPa).
 N verify (what is ?)
Infobox references
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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.
Safety
Perfluoroisobutene is highly toxic with an LCt = 880 mg⋅min⋅m (mice). 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.
PFIB is a product of pyrolysis of polytetrafluoroethylene (PTFE), one of the substances invoked to explain polymer fume fever.
See also
References
- ^ 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.