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Documenti fondamentali

E51309

Sigma-Aldrich

1-Penten-3-one

contains 0.1% BHT as stabilizer, 97%

Sinonimo/i:

Ethyl vinyl ketone

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About This Item

Formula condensata:
C2H5COCH=CH2
Numero CAS:
Peso molecolare:
84.12
Beilstein:
1735857
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

97%

Stato

liquid

contiene

0.1% BHT as stabilizer

Indice di rifrazione

n20/D 1.419 (lit.)

P. ebollizione

38 °C/60 mmHg (lit.)

Densità

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

Temperatura di conservazione

−20°C

Stringa SMILE

CCC(=O)C=C

InChI

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

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Descrizione generale

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.

Applicazioni

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.

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

14.0 °F - closed cup

Punto d’infiammabilità (°C)

-10 °C - closed cup

Dispositivi di protezione individuale

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


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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
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
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
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

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