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C101605

Sigma-Aldrich

1,3-Cyclohexanedione

97%

Synonym(s):

Dihydroresorcinol

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About This Item

Linear Formula:
C6H8(=O)2
CAS Number:
504-02-9
Molecular Weight:
112.13
Beilstein:
385888
EC Number:
207-980-0
MDL number:
MFCD00001585
UNSPSC Code:
12352100
PubChem Substance ID:
24892301
NACRES:
NA.22

Assay

97%

form

powder

contains

1-3% sodium chloride as stabilizer

mp

101-105 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C1CCCC(=O)C1

InChI

1S/C6H8O2/c7-5-2-1-3-6(8)4-5/h1-4H2

InChI key

HJSLFCCWAKVHIW-UHFFFAOYSA-N

Gene Information

human ... ACHE(43) , BCHE(590) , CES1(1066)

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Application

1,3-Cyclohexanedione can be used as a building block in the synthesis of:
  • 9-substituted 1,8-dioxo-xanthenes by reacting with unactivated aldehydes via aldol condensation/ Michael addition reaction.
  • [(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives by treating with phthalhydrazide, aromatic propargyloxy aldehydes, and azides via a four-component condensation reaction.
It can be also used to prepare 2-substituted adducts, which are important intermediates for the synthesis of ß-enaminones , polyhydroquinoline derivatives , 1,8-dioxo-dodecahydroxanthenes , spirocyclopentanols , oxathioles , and triquinanes.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Clean synthesis of 1, 8-dioxo-dodecahydroxanthene derivatives catalyzed by polyaniline-p-toluenesulfonate salt in aqueous media
John A, et al.
J. Mol. Catal. A: Chem., 248(1-2), 121-125 (2006)
Combining click-multicomponent reaction: one-pot synthesis of triazolyl methoxy-phenyl indazolo [2, 1-b] phthalazine-trione derivatives
Salehi P, et al.
Molecular Diversity, 16(2), 231-240 (2012)
K7 [PW11CoO40]-catalyzed one-pot synthesis of polyhydroquinoline derivatives via the Hantzsch three component condensation
Heravi MM, et al.
J. Mol. Catal. A: Chem., 264(1-2), 50-52 (2007)
Ytterbium triflate catalyzed synthesis of ?-enaminones
Epifano F, et al.
Tetrahedron Letters, 48(15), 2717-2720 (2007)
Reactions of methylated 5-chloro-1,2,3-thiadiazolium salts with cyclohexane-1,3-diones: X-ray crystal structure analysis of the thiapentalenic products
Gerrit L, et al.
Journal of the Chemical Society. Perkin Transactions 1, 3051-3051 (1993)
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