| Revision as of 10:47, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464357809 of page Isoprenol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 06:04, 30 December 2024 edit OAbot (talk | contribs)Bots440,440 editsm Open access bot: doi updated in citation with #oabot. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 420135793 |
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| verifiedrevid = 464369911 |
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| Name = Isoprenol |
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| Name = Isoprenol |
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| ImageFile = isoprenol.png |
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| ImageFile = Structural formula of isoprenol.svg |
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| ImageSize = 160px |
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| ImageSize = 200px |
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| ImageName = Skeletal formula of prenol |
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| ImageName = Structural formula of isoprenol |
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| ImageFile1 = Isoprenol-3D-balls.png |
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| ImageFile1 = Isoprenol-3D-balls.png |
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| ImageSize1 = 180px |
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| ImageSize1 = 180px |
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| ImageName1 = Ball-and-stick model of prenol |
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| ImageName1 = Ball-and-stick model of prenol |
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| IUPACName = 3-Methylbut-3-en-1-ol |
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| PIN = 3-Methylbut-3-en-1-ol |
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| OtherNames = 3-Methyl-3-buten-1-ol |
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| OtherNames = 3-Methyl-3-buten-1-ol |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3 |
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| InChI = 1/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3 |
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| SMILES = OCCC(=C)C |
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| SMILES = OCCC(=C)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3 |
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| StdInChI = 1S/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3 |
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| StdInChIKey = CPJRRXSHAYUTGL-UHFFFAOYSA-N |
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| StdInChIKey = CPJRRXSHAYUTGL-UHFFFAOYSA-N |
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| CASNo = 763-32-6 |
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| CASNo = 763-32-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EC-number = 212-110-8 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 12448 |
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| ChemSpiderID = 12448 |
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| PubChem = 12988 |
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| ChEBI = 62898 |
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| EC_number = 212-110-8 |
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| UNII = KJ25C8CPFA |
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| ChEMBL = 3561140 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Reference = <ref>{{Aldrich|id=W519308|accessdate=2009-08-31}}.</ref> |
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| Properties_ref = <ref>{{Aldrich|id=W519308|name=3-Methyl-3-buten-1-ol|accessdate=2009-08-31}}.</ref> |
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| Formula = C<sub>5</sub>H<sub>10</sub>O |
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| Formula = C<sub>5</sub>H<sub>10</sub>O |
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| MolarMass = 86.132 g/mol |
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| MolarMass = 86.132 g/mol |
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| BoilingPtC = 130 to 132 |
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| BoilingPt = 130–132 ºC |
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| Density = 0.853 g/cm<sup>3</sup> |
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| BoilingPt_notes = |
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| Density = 0.853 g/cm<sup>3</sup> |
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| RefractIndex = 1.433 |
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| RefractIndex = 1.433 |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| Reference = <ref>{{GHS class NZ|id=13375|accessdate = 2009-08-31}}.</ref> |
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| Hazards_ref = <ref>{{GHS class NZ|id=13375|access-date = 2009-08-31}}.</ref> |
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| GHSPictograms = {{GHS flame|Flam. Liq. 3}}{{GHS exclamation mark|Eye Irrit. 2}} |
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| EUIndex = not listed |
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| GHSSignalWord = WARNING |
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| GHSPictograms = {{GHS flame|Flam. Liq. 3}}{{GHS exclamation mark|Eye Irrit. 2}} |
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| HPhrases = {{H-phrases|226|319}} |
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| GHSSignalWord = WARNING |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|264|280|303+361+353|305+351+338|337+313|370+378|403+235|501}} |
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| HPhrases = {{H-phrases|226|319}} |
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| FlashPtC = 36 |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|264|280|303+361+353|305+351+338|337+313|370+378| 403+235|501}} |
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| FlashPt = 36 ºC (97 ºF)<ref group="note">Sigma-Aldrich Co. gives a value for the flash point of isoprenol of 42 ºC (108 ºF). The difference in the two values does not alter the safety classification of isoprenol as a category 3 flammable liquid under the ]; but the lower value quoted here (from the New Zealand Environmental Risk Management Authority) would make it a class IC flammable liquid instead of a class II combustible liquid under the U.S. ] classification (29 C.F.R § 1910.106), and F3 rather than F2 under the ] standard.</ref> |
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| FlashPt_ref = <ref group="note">Sigma-Aldrich Co. gives a value for the flash point of isoprenol of 42 °C (108 °F). The difference in the two values does not alter the safety classification of isoprenol as a category 3 flammable liquid under the ]; but the lower value quoted here (from the New Zealand Environmental Risk Management Authority) would make it a class IC flammable liquid instead of a class II combustible liquid under the U.S. ] classification (29 C.F.R § 1910.106), and F3 rather than F2 under the ] standard.</ref> |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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'''Isoprenol''', also known as '''3-methylbut-3-en-1-ol''', is a ] ]. It is produced industrially as an intermediate to ] (prenol): global production in 2001 can be estimated as 6–13 thousand tons.<ref name="SIDS-prenol">{{SIDS-ref|id=556821|name=3-Methyl-2-buten-1-ol|date=May 2005}}. Major produce in a world is BASF(Germany) and Kuraray(Japan).</ref> |
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==Synthesis== |
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Isoprenol is produced by the reaction between ] (2-methylpropene) and ], in what is arguably the simplest example of the ]. |
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The thermodynamically preferred prenol with the more substituted double bond cannot be directly formed in the above reaction, but is produced via a subsequent isomerisation: |
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This isomerisation reaction is catalyzed by any species which can form an ] without excessive ] of the substrate, for example poisoned palladium catalysts.<ref>See, e.g., {{citation | first1 = S. B. | last1 = Kogan | first2 = M. | last2 = Kaliya | first3 = N. | last3 = Froumin | title = Liquid phase isomerization of isoprenol into prenol in hydrogen environment | journal = Appl. Catal. A: Gen. | volume = 297 | issue = 2 | year = 2006 | pages = 231–36 | doi = 10.1016/j.apcata.2005.09.010}}.</ref> |
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==Uses== |
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Isoprenol is primarily a feedstock used in the production of other more valuable chemicals. Isoprenol and its prenol isomer are used together in the formation of ]s such as ].<ref>{{cite journal |last1=Bonrath |first1=Werner |last2=Gao |first2=Bo |last3=Houston |first3=Peter |last4=McClymont |first4=Tom |last5=Müller |first5=Marc-André |last6=Schäfer |first6=Christian |last7=Schweiggert |first7=Christiane |last8=Schütz |first8=Jan |last9=Medlock |first9=Jonathan A. |title=75 Years of Vitamin A Production: A Historical and Scientific Overview of the Development of New Methodologies in Chemistry, Formulation, and Biotechnology |journal=Organic Process Research & Development |date=15 September 2023 |volume=27 |issue=9 |pages=1557–1584 |doi=10.1021/acs.oprd.3c00161|doi-access=free }}</ref> It is also used in the synthesis of ] pesticides , ], and ]. |
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==Notes== |
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{{reflist|group="note"}} |
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==References== |
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{{reflist}} |
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] |
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] |