3-Methylbut-3-en-1-ol

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3-Methylbut-3-en-1-ol
IUPAC name 3-Methylbut-3-en-1-ol
Other names Isoprenol
Identifiers
InChI InChI=1/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3
InChIKey CPJRRXSHAYUTGL-UHFFFAOYAD
Standard InChI InChI=1S/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3
Standard InChIKey CPJRRXSHAYUTGL-UHFFFAOYSA-N
CAS number [763-32-6]
EC number 212-110-8
ChemSpider 12448
Properties[1]
Chemical formula C5H10O
Molar mass 86.132 g/mol
Density 0.853 g/cm3
Boiling point

130–132 ºC

Refractive index (nD) 1.433
Hazards[2]
EU index number not listed
GHS pictograms Flam. Liq. 3Eye Irrit. 2
GHS signal word WARNING
GHS hazard statements H226, H319
GHS precautionary statements P210, P233, P240, P241, P242, P243, P264, P280, P303+361+353, P305+351+338, P337+313, P370+378, P403+235, P501
Flash point 36 ºC (97 ºF)[note 1]
Related compounds
Other compounds 3-Methylbut-2-en-1-ol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

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 thousand tons.[3]

3-Methylbut-3-en-1-ol is produced by the reaction between 2-methylpropene (isobutene) and formaldehyde.

The reaction of isobutene with formaldehyde to give isoprenol, the first step in the industrial manufacture of prenol.


The thermodynamically preferred isomer with the more substituted double bond cannot be directly formed in this reaction, but isomerization yields the desired product:

The isomerization of isoprenol to prenol, the second step in the industrial manufacture of prenol.


The reaction is catalyzed by any species which can form an allyl complex without excessive hydrogenation of the substrate, for example poisoned palladium catalysts.[4]

Notes

  1. ↑ Sigma-Aldrich Co. gives a value for the flash point of 3-methylbut-3-en-1-ol of 42 ºC (108 ºF). The difference in the two values does not alter the safety classification of 3-methylbut-3-en-1-ol as a category 3 flammable liquid under the GHS; 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. OSHA classification (29 C.F.R § 1910.106), and F3 rather than F2 under the NFPA 704 standard.

References

  1. ↑ Source: Sigma-Aldrich Co., product no. W519308 (data accessed 2009-08-31).
  2. ↑ HSNO Chemical Classification Information Database, <http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=13375> (accessed 31 August 2009), New Zealand Environmental Risk Management Authority.
  3. ↑ 3-Methyl-2-buten-1-ol; SIDS Initial Assessment Report; Organisation for Economic Co-operation and Development, May 2005, <http://www.inchem.org/documents/sids/sids/556821.pdf>.
  4. ↑ See, eg, Kogan, S. B.; Kaliya, M.; Froumin, N. Liquid phase isomerization of isoprenol into prenol in hydrogen environment. Appl. Catal. A: Gen. 2006, 297 (2), 231–36. DOI: 10.1016/j.apcata.2005.09.010.
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