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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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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)
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)
Alkylation of Cyclic 1,3-Diketones
Thennati R, et al.
Synthetic Communications, 23, 3095-3095 (1993)
M T Zanni et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(20), 11265-11270 (2001-09-20)
The power of two-dimensional (2D) IR spectroscopy as a structural method with unprecedented time resolution is greatly improved by the introduction of IR polarization conditions that completely eliminate diagonal peaks from the spectra and leave only the crosspeaks needed for
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