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M39105

Sigma-Aldrich

3-Methyl-2-cyclohexenone

98%, Stabilized

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About This Item

Linear Formula:
CH3C6H7(=O)
CAS Number:
Molecular Weight:
110.15
Beilstein/REAXYS Number:
1560601
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

98%

refractive index

n20/D 1.494 (lit.)

bp

199-200 °C (lit.)

density

0.971 g/mL at 25 °C (lit.)

SMILES string

CC1=CC(=O)CCC1

InChI

1S/C7H10O/c1-6-3-2-4-7(8)5-6/h5H,2-4H2,1H3

InChI key

IITQJMYAYSNIMI-UHFFFAOYSA-N

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Application

3-Methyl-2-cyclohexenone is an insect sex pheromone of the Douglas-fir beetle. It can be used as a starting material:
  • In the total synthesis of (−)-ar-tenuifolene, a naturally occurring aromatic sesquiterpene.
  • To synthesize an organic building block 2-trimethylsilyl-3-methyl-cyclohexenone.
  • In the total synthesis of natural diterpenoids (+)-taiwaniaquinone H and (+)-dichroanone.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

154.4 °F

flash_point_c

68 °C

ppe

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


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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Catalytic enantioselective total synthesis of (−)-ar-Tenuifolene
Shaw K, et al.
Tetrahedron Letters, 61(20), 151850-151850 (2020)
Cyclic α-Acylvinyl Anionic Synthons: A Novel Synthesis of 2-Trimethylsilyl-3-methyl-cyclohexenone by the Wurtz-Fittig Coupling Reaction
Jyothi D and HariPrasad S
Synthetic Communications, 39(5), 875-879 (2009)
Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H
Li L-Q, et al.
Tetrahedron Letters, 55(43), 5960-5962 (2014)
Chemical transformation of 1, 8-cineole: synthesis of seudenone, an insect pheromone
Silvestre AJD, et al.
Industrial Crops and Products, 12(1), 53-56 (2000)
Aldrichimica Acta, 16, 41-41 (1983)

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