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E51309

Sigma-Aldrich

1-Penten-3-one

contains 0.1% BHT as stabilizer, 97%

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Synonym(s):
Ethyl vinyl ketone
Linear Formula:
C2H5COCH=CH2
CAS Number:
1629-58-9
Molecular Weight:
84.12
Beilstein:
1735857
MDL number:
MFCD00009316
UNSPSC Code:
12352100
PubChem Substance ID:
24894604
NACRES:
NA.22

Quality Level

200

Assay

97%

form

liquid

contains

0.1% BHT as stabilizer

refractive index

n20/D 1.419 (lit.)

bp

38 °C/60 mmHg (lit.)

density

0.851 g/mL at 20 °C
0.845 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

CCC(=O)C=C

InChI

1S/C5H8O/c1-3-5(6)4-2/h3H,1,4H2,2H3

InChI key

JLIDVCMBCGBIEY-UHFFFAOYSA-N

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Application

1-Penten-3-one can be used as a reactant to synthesize:
  • Conjugated dienes via palladium-catalyzed Heck reaction with vinyl bromides.
  • β-Amino carbonyl derivatives via solvent-free aza-Michael addition reaction with aromatic amines in the presence of ionic liquid catalyst.
  • α-Exo-methylene group bearing β-amino carbonyl compounds via ion-supported triphenylphosphine catalyzed aza‐Morita‐Baylis-Hillman reaction with N-tosyl arylimines.
Reagent for annulation.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Synlett, 51-51 (1991)
Yuvaraju N Balamraju et al.
Journal of the American Chemical Society, 126(37), 11522-11528 (2004-09-16)
Oxidative cleavage of arachidonate (C(20)) and linoleate (C(18)) phospholipids generates truncated C(8) or C(12) gamma-hydroxyalkenal phospholipids as well as C(5) or C(9) carboxyalkanoate phospholipids, which are abundant in atherosclerotic plaques. The gamma-hydroxyalkenals promote foam cell formation by scavenger receptor CD36-mediated
D L Morgan et al.
Inhalation toxicology, 13(8), 633-658 (2001-08-11)
The National Toxicology Program is conducting a chemical class study to investigate the structure-activity relationships for the toxicity of alpha,beta-unsaturated ketones. Ethyl vinyl ketone (EVK) was selected for study because it is a representative straight-chain aliphatic alpha,beta-unsaturated ketone with extensive
Yingju Xu et al.
The Journal of organic chemistry, 74(14), 5100-5103 (2009-06-03)
A general approach for the synthesis of 3,5-diarylcyclopentenones was developed. Key aspects of this approach are the intramolecular Friedel-Crafts-type cyclization of vinyl chlorides and subsequent Pd-catalyzed cross-coupling reactions. The requisite vinyl chloride-bearing arylacetic acid precursors are readily available by straightforward
C Deininger et al.
Journal of applied toxicology : JAT, 10(3), 167-171 (1990-06-01)
The mutagenic and genotoxic effects of ethylvinyl ketone were investigated. This alpha, beta-unsaturated carbonyl compound is widely distributed in the environment, in particular in food. Whereas ethylvinyl ketone shows only weak genotoxicity in the SOS Chromotest with Escherichia coli PQ37
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