View source for 3-Methylbut-3-en-1-ol

{{chembox
| Name = 3-Methylbut-3-en-1-ol
| IUPACName = 3-Methylbut-3-en-1-ol
|   OtherNames = Isoprenol
| Section1 = {{Chembox Identifiers
|   InChI = 1/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3
|   StdInChI = 1S/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3
|   InChIKey = CPJRRXSHAYUTGL-UHFFFAOYAD
|   StdInChIKey = CPJRRXSHAYUTGL-UHFFFAOYSA-N
|   CASNo = 763-32-6
|    CASNo_Ref = {{cascite}}
|   EC-number = 212-110-8
|   ChemSpiderID = 12448
  }}
| Section2 = {{Chembox Properties
|   Reference = <ref>{{Aldrich|id=W519308|accessdate=2009-08-31}}.</ref>
|   Formula = C<sub>5</sub>H<sub>10</sub>O
|   MolarMass = 86.132 g/mol
|   BoilingPt = 130–132 ºC
|   Density = 0.853 g/cm<sup>3</sup>
|   RefractIndex = 1.433
  }}
| Section7 = {{Chembox Hazards
|   Reference = <ref>{{GHS class NZ|id=13375|accessdate = 2009-08-31}}.</ref>
|   EUIndex = not listed
|   GHSPictograms = {{GHS flame|Flam. Liq. 3}}{{GHS exclamation mark|Eye Irrit. 2}}
|   GHSSignalWord = WARNING
|   HPhrases = {{H-phrases|226|319}}
|   PPhrases = {{P-phrases|210|233|240|241|242|243|264|280|303+361+353|305+351+338|337+313|370+378| 403+235|501}}
|   FlashPt = 36 ºC (97 ºF) <!--42 ºC (108 ºF)-->
  }}
| Section8 = {{Chembox Related
|   OtherCpds = [[3-Methylbut-2-en-1-ol]]
  }}
}}

'''3-Methylbut-3-en-1-ol''', also known as '''isoprenol''', is a [[hemiterpene]] [[alcohol]]. It is produced industrially as an intermediate to [[3-methylbut-2-en-1-ol]] (prenol): global production in 2001 can be estimated as 6–13&nbsp;thousand tons.<ref name="SIDS-prenol">{{SIDS-ref|id=556821|name=3-Methyl-2-buten-1-ol|date=May 2005}}.</ref>

3-Methylbut-3-en-1-ol is produced by the reaction between [[2-methylpropene]] (isobutene) and [[formaldehyde]].
[[File:Isoprenol prepn.png|left|435px|The reaction of isobutene with formaldehyde to give isoprenol, the first step in the industrial manufacture of prenol.]]<br clear="left"/>
The thermodynamically preferred isomer with the more substituted double bond cannot be directly formed in this reaction, but isomerization yields the desired product:
[[File:Prenol prepn.png|left|383px|The isomerization of isoprenol to prenol, the second step in the industrial manufacture of prenol.]]<br clear="left"/>
The reaction is catalyzed by any species which can form an [[allyl complex]] without excessive [[hydrogenation]], for example poisoned palladium catalysts.<ref>See, eg, {{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>

==References==
{{reflist}}

{{DEFAULTSORT:Methylbutenol-1, -2, 3-}}
[[Category:Hemiterpenes]]
[[Category:Alcohols]]
[[Category:Substituted alkenes]]

{{CC-BY-3.0}}