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| | 1,3-Cyclohexanedione Basic information |
| Product Name: | 1,3-Cyclohexanedione | | Synonyms: | Dihydro-1,3-benzenediol;NSC 57477;1,3-Cyclohexanedione, 97% 500GR;1,3-Cyclohexanedione 97%;1,3-Cyclohexanedione SynonyMs Cyclohexane-1,3-dione;1,3-Cyclohexanedione, 97+%, may cont. up to 1% NaCl;1,3-Cyclohexanedione [for HPLC Labeling];1,3-Diketocyclohexane | | 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 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 | | pka | 5.26(at 25℃) | | color | Pale yellow to beige | | Water Solubility | soluble | | Merck | 14,3178 | | BRN | 385888 | | InChI | 1S/C6H8O2/c7-5-2-1-3-6(8)4-5/h1-4H2 | | InChIKey | HJSLFCCWAKVHIW-UHFFFAOYSA-N | | SMILES | O=C1CCCC(=O)C1 | | LogP | 0.461 at 21.4℃ and pH3.2 | | Surface tension | 69.9mN/m at 1.01g/L and 22℃ | | CAS DataBase Reference | 504-02-9(CAS DataBase Reference) | | NIST Chemistry Reference | 1,3-Cyclohexanedione(504-02-9) | | EPA Substance Registry System | 1,3-Cyclohexanedione (504-02-9) |
| Safety Statements | 24/25 | | WGK Germany | 3 | | RTECS | GV0350000 | | F | 8-21 | | TSCA | TSCA listed | | HS Code | 29142900 | | Storage Class | 13 - Non Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Chronic 3
Eye Dam. 1 |
| | 1,3-Cyclohexanedione Usage And Synthesis |
| Chemical Properties | pale yellow to beige powder | | Uses | 1,3-Cyclohexanedione is used in organic synthesis and pharmaceutical intermediates. It is the intermediate of herbicides sulcotrione and nitrosulfonone. It is also nitisinone intermediate. | | Uses | 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 -enaminones , polyhydroquinoline derivatives , 1,8-dioxo-dodecahydroxanthenes , spirocyclopentanols , oxathioles , and triquinanes. | | Definition | ChEBI: 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 | | Synthesis | 1,3-cyclohexanedione is made by combining resorcinol with sodium formate in water using 5% palladium on carbon in water at a pH of 5-11. After the completion of the reaction, the catalyst is separated by filtration. Next, a sufficient amount of concentrated HCl is added to lower the pH of the mixture to about 3, and the reaction is cooled and stirred for an additional 0.5-4.0 hours. Optionally, sodium chloride may be added to facilitate recovery of 1,3-cyclohexanedione.
 | | Purification Methods | Crystallise 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.] |
| | 1,3-Cyclohexanedione Preparation Products And Raw materials |
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