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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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

19.4 °F - closed cup

Flash Point(C)

-7 °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’.

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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)
Yonggui Chi et al.
Journal of the American Chemical Society, 130(20), 6322-6323 (2008-04-25)
Non-interpenetrating star polymer catalysts designed to mimic the site isolation characteristics of enzymes enable the one-pot combination of multiple otherwise incompatible catalysts for asymmetric cascade reactions that involve iminium, enamine, and H-bonding catalysis. Control experiments replacing star polymer catalysts with
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
Kavita De et al.
The Journal of organic chemistry, 74(16), 6260-6265 (2009-07-23)
1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvents, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only
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