Isoprenol

Isoprenol
Names
	IUPAC name 3-Methylbut-3-en-1-ol
	Other names 3-Methyl-3-buten-1-ol
Identifiers
CAS Number	763-32-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	12448 ;
ECHA InfoCard	100.011.009
EC Number	212-110-8
	InChI InChI=1S/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3 Key: CPJRRXSHAYUTGL-UHFFFAOYSA-N ; InChI=1/C5H10O/c1-5(2)3-4-6/h6H,1,3-4H2,2H3;
	SMILES OCCC(=C)C;
Properties[1]
Chemical formula	C5H10O
Molar mass	86.132 g/mol
Density	0.853 g/cm3
Boiling point	130 to 132 °C (266 to 270 °F; 403 to 405 K)
Refractive index (nD)	1.433
Hazards[2]
GHS pictograms
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 °C (97 °F; 309 K)[note 1]
Related compounds
Related compounds	Prenol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Isoprenol, also known as 3-methylbut-3-en-1-ol, 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]

Isoprenol is produced by the reaction between isobutene (2-methylpropene) and formaldehyde.

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

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

↑ 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 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

↑ Sigma-Aldrich Co., 3-Methyl-3-buten-1-ol. Retrieved on 2009-08-31..
↑ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-08-31 .
↑ 3-Methyl-2-buten-1-ol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, May 2005 . Major produce in a world is BASF(Germany) and Kuraray(Japan).
↑ See, e.g., Kogan, S. B.; Kaliya, M.; Froumin, N. (2006), "Liquid phase isomerization of isoprenol into prenol in hydrogen environment", Appl. Catal. A: Gen., 297 (2): 231–36, doi:10.1016/j.apcata.2005.09.010 .

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[3] 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 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.

[1] Sigma-Aldrich Co., 3-Methyl-3-buten-1-ol. Retrieved on 2009-08-31..

[2] HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-08-31 .

[SIDS-prenol-4] 3-Methyl-2-buten-1-ol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, May 2005 . Major produce in a world is BASF(Germany) and Kuraray(Japan).

[5] See, e.g., Kogan, S. B.; Kaliya, M.; Froumin, N. (2006), "Liquid phase isomerization of isoprenol into prenol in hydrogen environment", Appl. Catal. A: Gen., 297 (2): 231–36, doi:10.1016/j.apcata.2005.09.010 .