M39105
3-Methyl-2-cyclohexenone
98%, Stabilized
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About This Item
Linear Formula:
CH3C6H7(=O)
CAS Number:
Molecular Weight:
110.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
214-769-7
Beilstein/REAXYS Number:
1560601
MDL number:
Assay:
98%
InChI key
IITQJMYAYSNIMI-UHFFFAOYSA-N
InChI
1S/C7H10O/c1-6-3-2-4-7(8)5-6/h5H,2-4H2,1H3
SMILES string
CC1=CC(=O)CCC1
assay
98%
refractive index
n20/D 1.494 (lit.)
bp
199-200 °C (lit.)
density
0.971 g/mL at 25 °C (lit.)
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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.
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
154.4 °F - closed cup
flash_point_c
68 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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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)
Catalytic enantioselective total synthesis of (−)-ar-Tenuifolene
Shaw K, et al.
Tetrahedron Letters, 61(20), 151850-151850 (2020)
Aldrichimica Acta, 16, 41-41 (1983)
Shoichiro Horita et al.
Chembiochem : a European journal of chemical biology, 16(3), 440-445 (2015-02-03)
(4R,6R)-Actinol can be stereo-selectively synthesized from ketoisophorone by a two-step conversion using a mixture of two enzymes: Candida macedoniensis old yellow enzyme (CmOYE) and Corynebacterium aquaticum (6R)-levodione reductase. However, (4S)-phorenol, an intermediate, accumulates because of the limited substrate range of
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