8.05901

Methyl vinyl ketone

(stabilised) for synthesis

• Synonym(s): Methyl vinyl ketone, 1-Buten-3-one, MVK, Vinyl methyl ketone
• CAS Number: 78-94-4
• Molecular Weight: 70.09
• MDL number: MFCD00008777
• UNSPSC Code: 12352115
• EC Index Number: 201-160-6
• NACRES: NA.22

Properties

• vapor pressure: 100 hPa ( 20 °C)
• Quality Level: 200
• form: liquid
• autoignition temp.: 491 °C
• potency: 23.1 mg/kg LD₅₀, oral (Rat); 35 mg/kg LD₅₀, skin (Rat)
• expl. lim.: 2.1-15.6 % (v/v)
• bp: 80-81 °C/1013 hPa
• transition temp: flash point -7 °C
• density: 0.85 g/cm³ at 20 °C
• storage temp.: 15-25°C
• InChI: 1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
• InChI key: FUSUHKVFWTUUBE-UHFFFAOYSA-N

Description

General description

Methyl vinyl ketone (MVK) is an organic compound that belongs to the class of enones. It is a useful synthetic reagent in organic synthesis for the preparation of various organic compounds. MVK is a 3-oxobutyl synthon, which undergoes a 1,4 conjugate addition (Michael addition) reaction. MVK is susceptible to anionic polymerization, therefore it is typically stored with hydroquinone, which inhibits polymerization.

Application

Methyl vinyl ketone can be used as a reagent to synthesize:

• Isocoumarins by a Pd-catalyzed regioselective cyclization reaction with o-alkynylbenzoates in the presence of LiCl.      
• Furan and pyrrole derivatives by Rh-catalyzed 1,4-carbonylative addition reaction with arylboronic acids.      
• Poly(p-hydroxystyrene) compounds via radical copolymerization with p-hydroxystyrene derivatives.     
• Aryl-thiocyanatobutan-2-one derivatives by reacting with aryldiazonium salts in the presence of copper(II) catalysts.

Analysis Note

Assay (GC, area%): ≥ 93.5 % (a/a)
Density (20°C/ 4°C): 0.850 - 0.860
Water (GC, area%): ≤ 5.0 % (a/a)
Identity (IR): passes test

Safety Information

• pictograms: GHS02,GHS05,GHS06,GHS09
• signalword: Danger
• hcodes: H225 - H300 + H310 + H330 - H314 - H317 - H410
• pcodes: P210 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - Skin Sens. 1
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 19.4 °F
• flash_point_c: -7 °C