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394483

Sigma-Aldrich

Cyclobutyl methyl ketone

98%

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About This Item

Linear Formula:
C4H7COCH3
CAS Number:
3019-25-8
Molecular Weight:
98.14
EC Number:
221-163-6
MDL number:
MFCD00037148
UNSPSC Code:
12352100
PubChem Substance ID:
24864600
NACRES:
NA.22

Quality Level

100

assay

98%

form

liquid

refractive index

n20/D 1.432 (lit.)

bp

137-139 °C/754 mmHg (lit.)

density

0.902 g/mL at 25 °C (lit.)

SMILES string

CC(=O)C1CCC1

InChI

1S/C6H10O/c1-5(7)6-3-2-4-6/h6H,2-4H2,1H3

InChI key

JPJOOTWNILDNAW-UHFFFAOYSA-N

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General description

Cyclobutyl methyl ketone (CMK, methyl cyclobutyl ketone) is an alicyclic ketone. It has been synthesized by reacting cyclobutanecarbonyl chloride with magnesium salt of malonic ester.[1] The mechanism of the photochemical reaction of gaseous mixtures of cyclobutyl methyl ketone diluted in argon has been studied by steady-state and pulsed (laser) photolysis.[2][3] It′s infrared (3500 to 30cm-1) and Raman (3200 to 30cm-1) spectra in gaseous and solid state has been recorded.[4] The UV spectra have been measured in alcohol and isooctane solution.[5] Study on the vapour phase thermal[6] and photodecomposition of methyl cyclobutyl ketone shows that the mode of decomposition is free radical in nature.[7]

Application

Cyclobutyl methyl ketone may be used as a model compound to study the oxidation mechanism of pinonic acid by hydroxyl radicals.[8][9]

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

84.2 °F - closed cup

flash_point_c

29 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK2472
SHBH9632
SHBD3543V
SHBD1414V
SHBB9644V

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Ultraviolet Absorption Spectra of Alicyclic Compounds. II. Methyl Cycloalkyl Ketones1.
Mariella RP and Raube RR
Journal of the American Chemical Society, 74(2), 518-521 (1952)
The photochemistry of cyclobutyl methyl ketone. Part 1.-Room-temperature results and the general mechanism.
Baldwin PJ, et al
J. Chem. Soc., Faraday II, 83(6), 1049-1058 (1987)
Experimental and theoretical study of aqueous cis-pinonic acid photolysis.
Lignell H, et al.
The Journal of Physical Chemistry A, 117(48), 12930-12945 (2013)
Azo-bis Nitriles. 1 Decomposition of Azo Compounds. A Special Case of Carbon-Carbon Hyperconjugation in a Free Radical Reaction.
Overberger CG and Lebovits A
Journal of the American Chemical Society, 76(10), 2722-2725 (1954)
The photochemistry of methyl cyclobutyl ketone. Part 2. Temperature dependence and the acetyl radical decomposition.
Baldwin PJ, et al
International Journal of Chemical Kinetics, 19(11), 997-1013 (1987)
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