Methyl vinyl ketone

Methyl vinyl ketone[1]
Skeletal formula of methyl vinyl ketone
Ball-and-stick model of the methyl vinyl ketone molecule
Names
Preferred IUPAC name
But-3-en-2-one
Other names
MVK
Methylene acetone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.055
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3 checkY
    Key: FUSUHKVFWTUUBE-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
    Key: FUSUHKVFWTUUBE-UHFFFAOYAV
SMILES
  • CC(=O)C=C
Properties
Chemical formula
 C4H6O
Molar mass 70.09 g/mol
Density 0.8407 g/cm3
Melting point −7 °C (19 °F; 266 K)
Boiling point 81.4 °C (178.5 °F; 354.5 K)
Hazards
GHS labelling:
Pictograms
 GHS06: ToxicGHS07: Exclamation markGHS02: FlammableGHS08: Health hazardGHS09: Environmental hazard
Signal word
 Danger
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
4
3
2
Flash point −7 °C (19 °F; 266 K)
Autoignition
temperature
 370 °C (698 °F; 643 K)
Explosive limits 2.1% v/v (lower), 15.6% v/v (higher)
Safety data sheet (SDS) Fisher Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a highly reactive compound. It is the simplest enone. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of organic compounds.[2][3]

Production

MVK has been prepared industrially by the condensation of acetone and formaldehyde, followed by dehydration. Similarly it is prepared by the Mannich reaction involving diethylammonium chloride and acetone, which produces the Mannich adduct:[2][4]

CH3C(O)CH3 + CH2O + [H2NEt2]Cl → [CH3C(O)CH2CH2N(H)Et2]Cl + H2O

Heating this ammonium salt releases the ammonium chloride and the MVK:[4]

[CH3C(O)CH2CH2N(H)Et2]Cl → CH3C(O)CH=CH2 + [H2NEt2]Cl

Reactivity and applications

MVK can act as an alkylating agent because it is an effective Michael acceptor. It gained early attention for its use in the Robinson annulation, a method useful in the preparation of steroids:

Robinson annulation reaction
Robinson annulation reaction

Its alkylating ability is both the source of its high toxicity and the feature that makes it a useful intermediate in organic synthesis. MVK will polymerize spontaneously. The compound is typically stored with hydroquinone, which inhibits polymerization.

Vinclozolin is a commercial fungicide prepared using MVK.

As an electrophilic alkene, it forms an adduct with cyclopentadiene. The resulting norbornene derivative is an intermediate in the synthesis of the anticholinergic drug biperiden. Via its cyanohydrin is also a precursor to vinclozolin. It is also a precursor to synthetic vitamin A.[2] MVK is used in the synthesis of Wieland–Miescher ketone.

Safety

MVK is extremely hazardous upon inhalation with an LD50 (rats) on the order of milligrams per cubic meter.[2]

References

  1. ^ Merck Index, 11th Edition, 6052.
  2. ^ a b c d Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.
  3. ^ Colapret, John A.; Buonora, Paul T.; Inomata, Kohei (2008). "Methyl Vinyl Ketone". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm276.pub2. ISBN 978-0-471-93623-7.
  4. ^ a b L. Wilds, Alfred; Nowak, Robert M.; McCaleb, Kirtland E. (1957). "1-Diethylamino-3-butanone". Organic Syntheses. 37: 18. doi:10.15227/orgsyn.037.0018.
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