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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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24894604
MDL number:
MFCD00009316
Beilstein/REAXYS Number:
1735857
Assay:
97%
Form:
liquid

Key Documents

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Product Name

1-Penten-3-one, contains 0.1% BHT as stabilizer, 97%

InChI

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

SMILES string

CCC(=O)C=C

InChI key

JLIDVCMBCGBIEY-UHFFFAOYSA-N

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

Quality Level

200

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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.

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.

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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

3 - Flammable liquids

wgk

WGK 3

flash_point_f

14.0 °F - closed cup

flash_point_c

-10 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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--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)
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)
Weijun Liu et al.
Journal of the American Chemical Society, 128(5), 1426-1427 (2006-02-02)
The cycloaddition between 1,3-cyclohexadiene and various enones and enals (methyl vinyl ketone, ethyl vinyl ketone, methacrolien) is accomplished at room temperature in yields ranging from 51 to 68% without the use of Lewis acids, high pressures, or microwave reactors. This
Eduardo C Meurer et al.
Journal of mass spectrometry : JMS, 37(2), 146-154 (2002-02-22)
Gas-phase reactions of acylium ions with alpha,beta-unsaturated carbonyl compounds were investigated using pentaquadrupole multiple-stage mass spectrometry. With acrolein and metacrolein, CH(3)-C(+)(double bond)O, CH(2)(double bond)CH-C(+)(double bond)O, C(6)H(5)-C(+)(double bond)O, and (CH(3))(2)N-C(+)(double bond)O react to variable extents by mono and double polar [4
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