Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Nonafluoro-tert-butyl alcohol: Difference between pages
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Saving copy of the {{chembox}} taken from revid 465842004 of page Trifluoromethanesulfonic_acid for the Chem/Drugbox validation project (updated: ''). |
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{{DISPLAYTITLE:Nonafluoro-''tert''-butyl alcohol}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Trifluoromethanesulfonic_acid|oldid=465842004}} 465842004] of page [[Trifluoromethanesulfonic_acid]] with values updated to verified values.}} |
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{{chembox |
{{chembox |
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| verifiedrevid = |
| verifiedrevid = 470614494 |
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| Name = |
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| ImageFile = Triflic-acid.png |
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| ImageFile = Nonafluoro-tert-butanol.png |
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| ImageFile2 = TfOH-3D-vdW.png |
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| ImageName = Nonafluoro-''tert''-butyl alcohol |
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| ImageSizeL1 = 120px |
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| IUPACName = Trifluoromethanesulfonic acid |
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| ImageSizeR1 = 100px |
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| OtherNames = Triflic acid |
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| PIN = 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-ol |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = perfluoro-tert-butyl alcohol, perfluoro-tert-butanol |
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| SystematicName = |
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| InChI = 1/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7) |
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| PubChem = 16924 |
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| InChIKey = ITMCEJHCFYSIIV-UHFFFAOYAW |
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| EC_number = 219-157-3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = InChI=1S/C4HF9O/c5-2(6,7)1(14,3(8,9)10)4(11,12)13/h14H | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 2378-02-1 | SMILES = OC(C(F)(F)F)(C(F)(F)F)C(F)(F)F }} |
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| StdInChI = 1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7) |
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| Section2 = {{Chembox Properties | Formula = C<sub>4</sub>F<sub>9</sub>OH | MolarMass = 236.04 g/mol | Appearance = Colorless liquid | BoilingPtC = 45 | Solubility = Miscible | pKa = 5.4 (in H<sub>2</sub>O) }} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Section3 = {{Chembox Hazards | MainHazards = Corrosive, eye irritant | FlashPt = | AutoignitionPt = }} |
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| StdInChIKey = ITMCEJHCFYSIIV-UHFFFAOYSA-N |
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| Section4 = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Section5 = |
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| Section6 = |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 48511 |
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| SMILES = C(F)(F)(F)S(=O)(=O)O |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = CF<sub>3</sub>SO<sub>3</sub>H |
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| MolarMass = 150.08 g/mol |
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| Appearance = Colorless liquid |
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| Density = 1.696 g/mL |
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| MeltingPt = −40 °C |
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| BoilingPt = 162 °C |
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| Solubility = Miscible |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Corrosive, eye irritant |
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| FlashPt = |
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| Autoignition = |
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}} |
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}} |
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'''Nonafluoro-''tert''-butyl alcohol''' (''IUPAC name'': '''1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol''') is a [[fluoroalcohol]]. It is the perfluorinated analog of [[Tert-Butyl alcohol|''tert''-butyl alcohol]]. Notably, as a consequence of its electron withdrawing fluorine substituents, it is very acidic for an alcohol, with a p''K''<sub>a</sub> value of 5.4, similar to that of a carboxylic acid. As another consequence of being a perfluorinated compound, it is also one of the lowest boiling alcohols, with a boiling point lower than that of [[methanol]]. |
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==Synthesis== |
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It is prepared by addition of trichloromethyllithium to [[hexafluoroacetone]], followed by halogen exchange with [[antimony pentafluoride]].<ref>{{Cite journal|last=Filler|first=Robert|last2=Schure|first2=Ralph M.|date=1967-04-01|title=Highly acidic perhalogenated alcohols. A new synthesis of perfluoro-tert-butyl alcohol|journal=The Journal of Organic Chemistry|language=EN|volume=32|issue=4|pages=1217–1219|doi=10.1021/jo01279a081|issn=0022-3263}}</ref> The aluminate derived from its alkoxide anion, tetrakis[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-oxy]aluminate(1–), {Al[(CF<sub>3</sub>)<sub>3</sub>CO]<sub>4</sub>}<sup>–</sup> is used as a [[weakly coordinating anion]].<ref>{{Cite journal|last=Krossing|first=Ingo|last2=Raabe|first2=Ines|date=2004-04-13|title=Noncoordinating Anions—Fact or Fiction? A Survey of Likely Candidates|journal=Angewandte Chemie International Edition|language=en|volume=43|issue=16|pages=2066–2090|doi=10.1002/anie.200300620|pmid=15083452|issn=1433-7851}}</ref> |
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== See also == |
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* [[2,2,2-Trifluoroethanol]] |
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* [[Hexafluoro-2-propanol|1,1,1,3,3,3-Hexafluoro-2-propanol]] |
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* [[Hexafluoroacetone]] |
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* [[Perfluorotriethylcarbinol]] |
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==References== |
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{{reflist}} |
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[[Category:Perfluorinated alcohols]] |
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[[Category:Tertiary alcohols]] |
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[[Category:Trifluoromethyl compounds]] |
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