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343447

Sigma-Aldrich

5-Isopropyl-1,3-cyclohexanedione

99% (GC)

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Linear Formula:
(CH3)2CHC6H7(=O)2
CAS Number:
Molecular Weight:
154.21
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

99% (GC)

form

solid

mp

63-65 °C (lit.)

shipped in

dry ice

SMILES string

[H]O[H].CC(C)C1CC(=O)CC(=O)C1

InChI

1S/C9H14O2.H2O/c1-6(2)7-3-8(10)5-9(11)4-7;/h6-7H,3-5H2,1-2H3;1H2

InChI key

JYJVWRORYGGPHA-UHFFFAOYSA-N

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1 of 4

This Item
38490361267125423
vibrant-m

343447

5-Isopropyl-1,3-cyclohexanedione

vibrant-m

38490

5,5-Dimethyl-1,3-cyclohexanedione

vibrant-m

361267

cis-1,2-Cyclohexanediol

vibrant-m

125423

1,4-Cyclohexanedione

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

mp

63-65 °C (lit.)

mp

146-148 °C (lit.)

mp

97-101 °C (lit.)

mp

77-78.5 °C (lit.)

form

solid

form

-

form

-

form

solid

shipped in

dry ice

shipped in

-

shipped in

-

shipped in

-

General description

5-Isopropyl-1,3-cyclohexanedione is a cyclic 1,3-diketone. It can be prepared by condensation of isobutylideneacetone with ethyl malonate. 5-Isopropyl-1,3-cyclohexanedione on methylation with methyl iodide yields 5-isopropyl-2-methyl-1,3-cyclohexanedione. A multistep-synthesis of 5-isopropyl-1,3-cyclohexanedione involving aldol condensation, Dieckmann-type annulation, ester hydrolysis and decarboxylation is reported.

Application

5-Isopropyl-1,3-cyclohexanedione may be used as starting reagent for the synthesis of carvotanacetone analogs. It may be used in the preparation of monocyclic terepenes. It may be used in the synthesis of 2H-pyrans, via reaction with α,β-unsaturated aldehydes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Monocyclic Terpenes from Cyclic 1, 3-Diketones1.
Frank RL and Hall Jr HK.
Journal of the American Chemical Society, 72(4), 1645-1648 (1950)
A Multistep Synthesis Featuring Classic Carbonyl Chemistry for the Advanced Organic Chemistry Laboratory.
Duff DB, et al.
Journal of Chemical Education, 89(3), 406-408 (2011)
Microwave-Assisted Solvent and Catalyst Free Synthesis of 2H-Pyrans.
Edayadulla N and Lee YR.
Bull. Korean Chem. Soc., 34(10), 2963-2963 (2013)

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