Skip to Content
Merck
All Photos(1)

Documents

E51309

Sigma-Aldrich

1-Penten-3-one

contains 0.1% BHT as stabilizer, 97%

Synonym(s):

Ethyl vinyl ketone

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
C2H5COCH=CH2
CAS Number:
Molecular Weight:
84.12
Beilstein:
1735857
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

General description

1-Penten-3-one also known as Ethyl vinyl ketone, is a straight-chain aliphatic α, β -unsaturated ketone, commonly used in the coupling reaction for the synthesis of diene and six-membered ring compounds.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synlett, 51-51 (1991)
Ruthenium-catalyzed oxidative cross-coupling reaction of activated olefins with vinyl boronates for the synthesis of (E, E)-1, 3-dienes
Dattatraya D H, et al.
The Journal of Organic Chemistry, 86, 3444-3455 (2021)
Ruthenium--Lewis Acid Catalyzed Asymmetric Diels--Alder Reactions between Dienes and alpha beta Unsaturated Ketones
Jenny R, et al.
Chemistry?A European Journal , 13, 3354-3368 (2007)
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service