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Merck
CN

E51309

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

Key Documents

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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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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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCB1958
BCBL2542V
BCBD1533V
MKBB9894
1434052

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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.
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
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