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E51309

Sigma-Aldrich

1-Penten-3-one

contains 0.1% BHT as stabilizer, 97%

Synonym(s):

Ethyl vinyl ketone

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About This Item

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

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

14.0 °F - closed cup

Flash Point(C)

-10 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synlett, 51-51 (1991)
E Eder et al.
Mutation research, 470(1), 29-37 (2000-09-15)
alpha,beta-Unsaturated ketones are bifunctional compounds which form promutagenic 1,N(2)-propanodeoxyguanosine adducts like carcinogenic alpha,beta-unsaturated aldehydes and are mutagenic and genotoxic like these aldehydes. They are important industrial chemicals, are found in our environment and are widespread in our food. We investigated
Yichi Xu et al.
Journal of food science, 75(4), C352-C358 (2010-06-16)
The release of volatiles from tomatillos (Physalis ixocarpa Brot.) and tomatoes in the mouthspace and nosespace was measured in real-time using selected ion flow tube mass spectrometry (SIFT-MS). (Z)-3-Hexenal, (E)-2-hexenal, hexanal, and 1-penten-3-one increased, while isobutyl alcohol, nonanal, and methylbutanal
V Kettmann et al.
Acta crystallographica. Section C, Crystal structure communications, 57(Pt 6), 737-739 (2001-06-16)
The title compound, C18H19N3O2, was obtained by an azo-coupling reaction with enaminones and is composed of a planar azoenamine skeleton which forms a six-membered ring through a symmetrical intramolecular hydrogen bond. The compound was found to exist as an equilibrium
E Eder et al.
Chemical research in toxicology, 4(1), 50-57 (1991-01-01)
The reaction of the alpha, beta-unsaturated ketones methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) with nucleosides and 5'-mononucleotides was studied. The genotoxic activity of MVK and EVK in the SOS Chromotest was investigated. Three different types of adducts
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