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M87509

Sigma-Aldrich

3-Buten-2-one

contains 0.3-1.0% hydroquinone as stabilizer, technical grade, 90%

Synonym(s):

Methyl vinyl ketone, Vinyl methyl ketone

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About This Item

Linear Formula:
CH2=CHCOCH3
CAS Number:
78-94-4
Molecular Weight:
70.09
Beilstein:
506021
MDL number:
MFCD00008777
UNSPSC Code:
12352100
PubChem Substance ID:
24897283
NACRES:
NA.22

grade

technical grade

Quality Level

200

vapor density

1.3 (vs air)

vapor pressure

310 mmHg ( 55 °C)
71 mmHg ( 20 °C)

Assay

90%

form

liquid

contains

0.3-1.0% hydroquinone as stabilizer

expl. lim.

15.64 %

impurities

<7% water

refractive index

n20/D 1.411 (lit.)

bp

81 °C (lit.)

solubility

H2O: soluble

density

0.864 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=O)C=C

InChI

1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3

InChI key

FUSUHKVFWTUUBE-UHFFFAOYSA-N

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Application

3-Buten-2-one can undergo conjugate addition with methanol over the solid base catalysts to afford 4-methoxy-butan-2-one. It can also undergo coupling reaction with alkyltins and alkynes in the presence of a nickel complex to form stereo-defined conjugated enynes.

Signal Word

Danger

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Synthesis of stereodefined enynes by the nickel-catalyzed coupling reaction of alkynyltins, alkynes, and enones.
Ikeda SI
Journal of the American Chemical Society, 116(13), 5975-5976 (1994)
Conjugate addition of methanol to 3-buten-2-one over solid base catalysts.
Kabashima H, et al.
Applied Catalysis A: General, 214(1), 121-124 (2001)
Laura L Thomas et al.
Journal of the American Chemical Society, 132(9), 3097-3104 (2010-02-13)
Quantum and molecular mechanics calculations for the Diels-Alder reactions of cyclopentadiene with 1,4-naphthoquinone, methyl vinyl ketone, and acrylonitrile have been carried out at the vacuum-water interface and in the gas phase. In conjunction with previous studies of these cycloadditions in
Palladium-mediated annulation of vinyl aziridines with Michael acceptors: stereocontrolled synthesis of substituted pyrrolidines and its application in a formal synthesis of (-)-α-kainic acid.
Martin A Lowe et al.
Angewandte Chemie (International ed. in English), 50(28), 6370-6374 (2011-06-01)
Quan Cai et al.
Organic letters, 14(12), 3040-3043 (2012-05-26)
A formal [4 + 2] cycloaddition of 2,3-disubstituted indoles with vinyl methyl ketone was realized in the presence of a catalytic amount of quinine-derived primary amine and pentafluorobenzoic acid. This method provides bridged-ring indoline scaffolds containing two quaternary carbon centers
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