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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
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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]
  • [(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.[2]
It can be also used to prepare 2-substituted adducts, which are important intermediates for the synthesis of ß-enaminones [3], polyhydroquinoline derivatives [4], 1,8-dioxo-dodecahydroxanthenes [5], spirocyclopentanols [6], oxathioles [7], and triquinanes.[8]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000423630
0000358088
0000358088
0000280084
0000280083

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Alkylation of Cyclic 1,3-Diketones
Thennati R, et al.
Synthetic Communications, 23, 3095-3095 (1993)
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)
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)
Xiao-Qing Zhao et al.
Talanta, 80(1), 242-245 (2009-09-29)
A rapid and sensitive flow injection fluorometry has been developed for the determination of formaldehyde based on the microwave on-line accelerating its Hantzsch reaction with cyclohexane-1,3-dione. Under the optimized conditions, the fluorescent intensity is proportional to formaldehyde content in the
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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