Isoprenol

Isoprenol
Names
	Preferred 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;
ChEBI	CHEBI:62898;
ChEMBL	ChEMBL3561140;
ChemSpider	12448 ;
ECHA InfoCard	100.011.009
EC Number	212-110-8;
PubChem CID	12988;
UNII	KJ25C8CPFA;
CompTox Dashboard (EPA)	DTXSID4052506 ;
	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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H319
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P403+P235, 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). verify (what is ?) 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 reaction of isobutene with formaldehyde to give isoprenol, the first step in the industrial manufacture of prenol.

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:

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

This isomerisation 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.