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1,3-Cyclohexanedione

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1,3-Cyclohexanedione Basic information
Product Name:1,3-Cyclohexanedione
Synonyms:1,3-Benzenediol, dihydro-;Hydroresorcinol;Resorcinol, dihydro-;1,3-CYCHEXANEDIONE;1,3-cycloadipic ketone;1,3-CYCLOHEXANEDIONE, FOR FLUORESCENCE;1,3-Cyclohexanedione, 97+%;1,3-Cyclohexanedione,98%
CAS:504-02-9
MF:C6H8O2
MW:112.13
EINECS:207-980-0
Product Categories:ketone;Intermediates;Isotope Labelled Compounds;Analytical Chemistry;Carbonyl Group Labeling Reagents for Fluorescence HPLC;Fluorescence Detection (HPLC Labeling Reagents);HPLC Labeling Reagents;cyclic compounds;bc0001;Amidite
Mol File:504-02-9.mol
1,3-Cyclohexanedione Structure
1,3-Cyclohexanedione Chemical Properties
Melting point 101-105 °C (lit.)
Boiling point 170.05°C (rough estimate)
density 1,1 g/cm3
vapor pressure 0.018Pa at 25℃
refractive index 1.4576 (estimate)
storage temp. Store at +2°C to +8°C.
solubility Chloroform (Slightly), Methanol (Slightly)
form Powder
pka5.26(at 25℃)
color Pale yellow to beige
Water Solubility soluble
Merck 14,3178
BRN 385888
LogP0.461 at 21.4℃ and pH3.2
Surface tension69.9mN/m at 1.01g/L and 22℃
CAS DataBase Reference504-02-9(CAS DataBase Reference)
NIST Chemistry Reference1,3-Cyclohexanedione(504-02-9)
EPA Substance Registry System1,3-Cyclohexanedione (504-02-9)
Safety Information
Safety Statements 24/25
WGK Germany 3
RTECS GV0350000
8-21
TSCA Yes
HS Code 29142900
MSDS Information
ProviderLanguage
Dihydroresorcinol English
SigmaAldrich English
ACROS English
ALFA English
1,3-Cyclohexanedione Usage And Synthesis
Chemical Propertiespale yellow to beige powder
Uses1,3-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 ?-enaminones , polyhydroquinoline derivatives , 1,8-dioxo-dodecahydroxanthenes , spirocyclopentanols , oxathioles , and triquinanes.
Uses1,3-Cyclohexanedione is used in organic synthesis and pharmaceutical intermediates. It is the intermediate of herbicides sulcotrione and nitrosulfonone. It is also nitisinone intermediate.
DefinitionChEBI: 1,3-Cyclohexanedione is a cyclohexanedione carrying oxo substituents at positions 1 and 3. It is a beta-diketone and a cyclohexanedione.
Synthesis Reference(s)The Journal of Organic Chemistry, 30, p. 3206, 1965 DOI: 10.1021/jo01020a506
Purification MethodsCrystallise the dione from *benzene. Dissolve ~50g of the diol in 140mL of *C6H6 under N2, cool, collect the solid and dry it in a vacuum desiccator overnight. It is unstable and should be stored under N2 or Ar at ~0o. [Thompson Org Synth Coll Vol III 278 1955, Beilstein 7 IV 1985.]
Tag:1,3-Cyclohexanedione(504-02-9) Related Product Information
Cyclohexane 5,5-Dimethylhydroresorcinol(5,5-Dimethyl-1,3-Cyclohexanedione) 2,5-Hexanedione 5-(4-CHLOROPHENYL)-1,3-CYCLOHEXANEDIONE 5-PHENYLCYCLOHEXANE-1,3-DIONE 1,3-Cyclohexanedione, 2-methyl-,2-Methyl-1,3-cyclohexanedione, 98+% CYCLOHEXANEDIONE,1,4-Cyclohexanedione,98% 1,2-CYCLOHEXANEDIONE,1,2-Cyclohexanedione, 98+%,1,2-Cyclohexanedione,97% 4,4-Dimethyl-1,3-cyclohexanedione, GC 98% 5-ISOPROPYL-1,3-CYCLOHEXANEDIONE 2-ACETYL-1,3-CYCLOHEXANEDIONE 5-METHYLCYCLOHEXANE-1,3-DIONE 1,4-Dioxaspiro[4.5]decan-8-one 2-Ethyl-1,3-cyclopentanedione 1,2-CYCLOHEXANEDIONE DIOXIME 2-Methyl-1,3-cyclopentanedione 1,3-CYCLOHEXADIENE 1,3-Cyclohexanedione99%

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