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Wikipedia

Methyl vinyl ketone

January 01, 1970

"MVK" redirects here. For the gene, see MVK (gene). For the Hungarian transport company, see MVK Zrt.

Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. 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 other compounds.[2]

Methyl vinyl ketone[1]
Names
Preferred IUPAC name
But-3-en-2-one
Other names
MVK
Methylene acetone
Identifiers
  • 78-94-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:48058 Y
ChemSpider
  • 6322 Y
ECHA InfoCard 100.001.055
  • 6570
UNII
  • AR7642I1MP Y
  • DTXSID3025671
  • InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3 Y
    Key: FUSUHKVFWTUUBE-UHFFFAOYSA-N Y
  • InChI=1/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
    Key: FUSUHKVFWTUUBE-UHFFFAOYAV
  • CC(=O)C=C
Properties
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:
Danger
NFPA 704 (fire diamond)
Health 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
3
2
Flash point −7 °C (19 °F; 266 K)
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).
Y verify (what is YN ?)

Production edit

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][3]

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

Heating this ammonium salt releases the ammonium chloride and the MVK:[3]

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

Reactivity and applications edit

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

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 an intermediate in the synthesis of some pharmaceutical drugs including etorphine, buprenorphine, tolquinzole, butaclamol, and etretinate.[citation needed]

MVK is used in the synthesis of Wieland–Miescher ketone.

Safety edit

MVK is extremely hazardous upon inhalation causing coughing, wheezing and shortness of breath even at low concentrations. It will also readily cause irritation of the skin, eyes, and mucous membranes.

References edit

  1. ^ Merck Index, 11th Edition, 6052.
  2. ^ a b c Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3527306732.
  3. ^ 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.

External links edit

  • NJ Hazardous Substance Factsheet for methyl vinyl ketone
  • MSDS for methyl vinyl ketone 2006-10-15 at the Wayback Machine
  • . Sander, R. 1999-04-08.

January 01, 1970
methyl, vinyl, ketone, redirects, here, gene, gene, hungarian, transport, company, iupac, name, butenone, organic, compound, with, formula, ch3c, reactive, compound, classified, enone, fact, simplest, example, thereof, colorless, flammable, highly, toxic, liqu. MVK redirects here For the gene see MVK gene For the Hungarian transport company see MVK Zrt Methyl vinyl ketone MVK IUPAC name butenone is the organic compound with the formula CH3C O CH CH2 It is a reactive compound classified as an enone in fact the simplest example thereof 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 other compounds 2 Methyl vinyl ketone 1 Names Preferred IUPAC name But 3 en 2 one Other names MVKMethylene acetone Identifiers CAS Number 78 94 4 Y 3D model JSmol Interactive image ChEBI CHEBI 48058 Y ChemSpider 6322 Y ECHA InfoCard 100 001 055 PubChem CID 6570 UNII AR7642I1MP Y CompTox Dashboard EPA DTXSID3025671 InChI InChI 1S C4H6O c1 3 4 2 5 h3H 1H2 2H3 YKey FUSUHKVFWTUUBE UHFFFAOYSA N YInChI 1 C4H6O c1 3 4 2 5 h3H 1H2 2H3Key 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 Signal word Danger NFPA 704 fire diamond 432 Flash point 7 C 19 F 266 K Autoignitiontemperature 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 Y verify what is Y N Infobox references Contents 1 Production 2 Reactivity and applications 3 Safety 4 References 5 External linksProduction editMVK 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 3 CH3C O CH3 CH2O H2NEt2 Cl CH3C O CH2CH2N H Et2 Cl H2O Heating this ammonium salt releases the ammonium chloride and the MVK 3 CH3C O CH2CH2N H Et2 Cl CH3C O CH CH2 H2NEt2 ClReactivity and applications editMVK 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 nbsp 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 nbsp 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 an intermediate in the synthesis of some pharmaceutical drugs including etorphine buprenorphine tolquinzole butaclamol and etretinate citation needed MVK is used in the synthesis of Wieland Miescher ketone Safety editMVK is extremely hazardous upon inhalation causing coughing wheezing and shortness of breath even at low concentrations It will also readily cause irritation of the skin eyes and mucous membranes References edit Merck Index 11th Edition 6052 a b c Siegel H Eggersdorfer M Ketones Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a15 077 ISBN 978 3527306732 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 External links editNJ Hazardous Substance Factsheet for methyl vinyl ketone MSDS for methyl vinyl ketone Archived 2006 10 15 at the Wayback Machine Compilation of Henry s law constants for inorganic and organic species of potential importance in environmental chemistry Sander R 1999 04 08 Retrieved from https en wikipedia org w index php title Methyl vinyl ketone amp oldid 1216749196, wikipedia, wiki, book, books, library,

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