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Sigma-Aldrich

3-Methyl-2-cyclopentenone

97%

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About This Item

Linear Formula:
CH3C5H5(=O)
CAS Number:
Molecular Weight:
96.13
Beilstein/REAXYS Number:
1280476
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.488 (lit.)

bp

74 °C/15 mmHg (lit.)

mp

3-5 °C (lit.)

density

0.980 g/mL at 20 °C
0.971 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1=CC(=O)CC1

InChI

1S/C6H8O/c1-5-2-3-6(7)4-5/h4H,2-3H2,1H3

InChI key

CHCCBPDEADMNCI-UHFFFAOYSA-N

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General description

3-Methyl-2-cyclopentenone undergoes reduction in presence of triethylammonium formate and palladium catalyst to form saturated ketone. It undergoes B(C6F5)3 catalyzed hydrosilation to yield complex reaction mixtures of 1,2 addition products and oligomers.

Application

3-Methyl-2-cyclopentenone was used in the synthesis of 2-hydroxy-3-methyl-2-cyclopentenone.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

149.0 °F - closed cup

flash_point_c

65 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


Certificates of Analysis (COA)

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A new synthesis of cyclopentenones: dihydrojasmone.
Hendrickson JB and Palumbo PS.
The Journal of Organic Chemistry, 50(12), 2110-2112 (1985)
Palladium-catalyzed reductions of. alpha.,. beta.-unsaturated carbonyl compounds, conjugated dienes, and acetylenes with trialkylammonium formates.
Cortese NA and Heck NA.
The Journal of Organic Chemistry, 43(20), 3985-3987 (1978)
B(C6F5)3 catalyzed hydrosilation of enones and silyl enol ethers.
Blackwell JM, et al.
Tetrahedron, 58(41), 8247-8254 (2002)

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