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3-Methyl-2-pentanone

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3-Methyl-2-pentanone
Structure of 3-methyl-2-pentanone
Names
IUPAC name
3-Methyl-2-pentanone
Other names
3-Methylpentan-2-one; Methyl sec-butyl ketone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.439 Edit this at Wikidata
EC Number
  • 209-282-1
  • InChI=1S/C6H12O/c1-4-5(2)6(3)7/h5H,4H2,1-3H3
    Key: UIHCLUNTQKBZGK-UHFFFAOYSA-N
  • InChI=1/C6H12O/c1-4-5(2)6(3)7/h5H,4H2,1-3H3
    Key: UIHCLUNTQKBZGK-UHFFFAOYAL
  • CCC(C)C(=O)C
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance Colorless liquid
Odor Peppermint-like
Density 0.8130 g/mL (20 °C)
Melting point −83 °C (−117 °F; 190 K)
Boiling point 116 °C (241 °F; 389 K)
2.26 wt % (20 °C)
1.4012 (20 °C)
Hazards
Flash point 12 °C (54 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Methyl-2-pentanone (methyl sec-butyl ketone) is an aliphatic ketone and isomer of 2-hexanone. It is used as a solvent and as an intermediate for syntheses. Its industrial importance is low. It is produced by base-catalyzed aldol condensation of 2-butanone with acetaldehyde, forming 4-hydroxy-3-methyl-2-pentanone, which is dehydrated to 3-methyl-3-penten-2-one over an acid catalyst, followed by hydrogenation over a palladium catalyst.[1]

References

  1. ^ Hardo Siegel, Manfred Eggersdorfer (2007), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5
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