| 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()) |
| (40 intermediate revisions by 27 users not shown) |
| Line 1: |
Line 1: |
|
|
{{More citations needed|date=December 2022}} |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| ImageFile = Perfluoroisobutene.svg |
|
|
|
| Watchedfields = changed |
|
| ImageSize = 160px |
|
|
|
| verifiedrevid = 379575756 |
| ⚫ |
| IUPACName = 1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene |
|
|
⚫ |
| 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 |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo = 382-21-8 |
|
|
| PubChem = 61109 |
|
| CASNo = 382-21-8 |
|
|
| ChEMBL = 4634291 |
| ⚫ |
| SMILES = C(=C(F)F)(C(F)(F)F)C(F)(F)F |
|
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| InChI = 1/C4F8/c5-2(6)1(3(7,8)9)4(10,11)12 |
|
|
| RTECS = UD1800000 |
|
| 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 |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>4</sub>F<sub>8</sub> |
|
| Formula = C<sub>4</sub>F<sub>8</sub> |
|
| MolarMass = 200.030 g/mol |
|
| MolarMass = 200.030 g/mol |
|
| Appearance = |
|
| Appearance = colorless gas |
|
| Density = 8.2 g/l |
|
| Density = 8.2 g/l |
|
| MeltingPt = |
|
| MeltingPtC = −130 |
|
| BoilingPt = 7.0 °C (280 K) |
|
| BoilingPtC = 7.0 |
|
| Solubility = |
|
| BoilingPt_notes = |
|
|
| Solubility = |
| ⚫ |
}} |
|
| ⚫ |
| Section3 = {{Chembox Hazards |
|
| ⚫ |
| MainHazards = |
|
| ⚫ |
| FlashPt = |
|
|
| Autoignition = |
|
|
}} |
|
}} |
|
⚫ |
|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 = |
|
|
| AutoignitionPt = |
|
⚫ |
}} |
|
}} |
|
}} |
|
|
|
|
|
|
'''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 causing ]. |
|
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== |
|
⚫ |
* |
|
* |
|
| ⚫ |
* |
|
|
|
|
|
|
|
{{Chemical agents}} |
| ⚫ |
] |
|
| ⚫ |
] |
|
|
] |
|
|
|
|
|
|
⚫ |
] |
|
] |
|
|
⚫ |
] |
|
] |
|
|
|
] |
|
] |
|