but-3-en-2-one

• ChemBase ID: 104368
• Molecular Formular: C4H6O
• Molecular Mass: 70.08984
• Monoisotopic Mass: 70.04186481
• SMILES: CC(=O)C=C
• Canonical SMILES: CC(=O)C=C
• InChI: InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
• InChIKey: FUSUHKVFWTUUBE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: but-3-en-2-one
• IUPAC Traditional name: methyl vinyl ketone
• Synonyms: Methyl vinyl ketone; 3-Buten-2-one; METHYL VINYL KETONE; METHYL VINYL KETONE (STABILIZED); Butenone; Methyl vinyl ketone; MVK; Methylene acetone; Vinyl methyl ketone; 3-Buten-2-one; 丁烯酮; 甲基乙烯酮; 丁烯酮; 甲基乙烯基酮; 3-丁烯-2-酮

Database IDs

• CAS Number: 78-94-4
• EC Number: 201-160-6
• MDL Number: MFCD00008777
• Beilstein Number: 506021
• Merck Index: 146134
• PubChem SID: 24885962; 24897283; 162091530; 24856333
• PubChem CID: 6570
• CHEBI ID: 48058
• Chemspider ID: 6322
• Wikipedia Title: Methyl_vinyl_ketone

CALCULATED PROPERTIES

• Acid pKa: 19.94529
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.8625728
• LogD (pH = 7.4): 0.8625728
• Log P: 0.8625728
• Molar Refractivity: 20.8425 cm^3
• Polarizability: 7.9271245 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -7 °C (20 °F); -7°C; -7 °C; -7°C
• Boiling Point: 32-34°C/60mm; 34 °C/120 mmHg(lit.); 81.4 °C (178.5 °F); 81.4°C; 81.4 °C
• Flash Point: 19.4 °F; -6.6°C; -6°C(21°F); -7 °C
• Auto Ignition Point: 491 °C (915 °F)
• Density: 0.836 at 20 °C (water = 1); 0.836 g/ml; 0.8407 g/cm^3; 0.856; 0.86 g/mL at 20 °C; 0.864 g/mL at 25 °C(lit.)
• Refractive Index: 1.4120; n20/D 1.411(lit.); n20/D 1.412
• Vapor Pressure: 310 mmHg ( 55 °C); 71 mmHg ( 20 °C); 83.9 mm Hg at 25 °C (SRC), 160 mbar (120 mm Hg) at 34 °C
• Vapor Density: 1.3 (vs air); 2.41 (air = 1)

Safety Information

• Storage Condition: 0°C
• RTECS: EM9800000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Highly toxic (T+)
• UN Number: 1251; UN1251
• German water hazard class: 3
• Hazard Class: 3/8; 6.1
• Packing Group: 1; I; Truck Only
• Australian Hazchem: 2WE
• Risk Statements: 11-26/27/28-34-40-43-50/53-68; 11-26/27/28-34-43-50/53; 11-26/28-34; R:9-11-20-28-43; R:9-20-28-43
• Safety Statements: 16-26-28-36/37/39-45-61; 4-7/9-20-26-28-33-36/37/39-45-60; S:16-28-29-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: TF1
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 131P
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  3

  4

  2
• Explode Limits: 15.64 %
• GHS Hazard statements: H225-H300 +H310 + H330-H314-H317-H341-H351-H410; H225-H300 +H310 + H330-H314-H317-H410; H225-H300-H330-H314-H318
• GHS Precautionary statements: P210-P260-P264-P273-P280-P284; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1251 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); 90%; 99%; tech. 90%, stab. with 0.5% hydroquinone
• Grade: purum; technical grade
• Impurities: ~5% water; <7% water
• Contains: ~0.5% acetic acid as stabilizer; ~0.5% hydroquinone as stabilizer; 0.3-1.0% hydroquinone as stabilizer; 0.5% hydroquinone and 0.1% acetic acid as stabilizer
• Linear Formula: CH2=CHCOCH3

DETAILS

MP Biomedicals - 05206832

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155704

(3-Buten-2-one) 1 ml = approx. 0.86 g Stabilized with 1% hydroquinone

Sigma Aldrich - M87509

Packaging
100, 500 mL in glass bottle

Sigma Aldrich - 269549

Application
Michael acceptor for thiols1, indoles2 and coumarins3
Substrate used in an iron(II)-catalyzed alkylation of indoles at the C-3 position. Use of excess vinyl ketone provides the 2,3-dialkylated indoles.
Packaging
5, 100, 500 mL in glass bottle

Sigma Aldrich - 69692

Caution
may discolor to brown on storage

REFERENCES

• For an example of the conjugate addition of aldehydes (Stetter reaction), see: Org. Synth. Coll., 8, 620 (1993); for reaction scheme, see 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, L08750.
• For examples of use as a building block in asymmetric syntheses, see: Org. Synth. Coll., 7, 363 (1990); 9, 610 (1998); for reaction schemes for these, see 2-Methylcyclopentane-1,3-dione, A13936, and (S)-(-)-1-Phenylethylamine, A12632, respectively.