| Identification | More | [Name]
2-Methyl-1,3-cyclohexanedione | [CAS]
1193-55-1 | [Synonyms]
1,3-DIMETHYLCYCLOADIPIC KETONE
2-MECHD
2-METHYL-1,3-CYCLOHEXANDIONE
2-METHYL-1,3-CYCLOHEXANEDIONE
2-METHYLCYCLOHEXANE-1,3-DIONE
NSC 54460
1-Methyl-2,6-cyclohexanedione
2-Methyl-1,3-cyclohexanedione, 98+%
1,3-Cyclohexanedione, 2-methyl-
2-METHYLCYCLOHEXANE-1,3-DIONE, 98+%
2-METHYL-1,3-CYCLOHEXANEDIONE (SEE 2625) | [EINECS(EC#)]
214-773-9 | [Molecular Formula]
C7H10O2 | [MDL Number]
MFCD00001587 | [Molecular Weight]
126.15 | [MOL File]
1193-55-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to salmon powder | [Melting point ]
206-208 °C (lit.) | [Boiling point ]
194.28°C (rough estimate) | [density ]
1.0579 (rough estimate) | [refractive index ]
1.4660 (estimate) | [storage temp. ]
0-6°C | [solubility ]
methanol: 0.1 g/mL, clear
| [form ]
Powder, Crystals or Crystalline Powder | [pka]
5.58±0.25(Predicted) | [color ]
Off-white to salmon to pale brown | [Water Solubility ]
INSOLUBLE | [Sensitive ]
Hygroscopic | [BRN ]
1281598 | [InChI]
1S/C7H10O2/c1-5-6(8)3-2-4-7(5)9/h5H,2-4H2,1H3 | [InChIKey]
VSGJHHIAMHUZKF-UHFFFAOYSA-N | [SMILES]
CC1C(=O)CCCC1=O | [LogP]
-0.390 (est) | [CAS DataBase Reference]
1193-55-1(CAS DataBase Reference) | [NIST Chemistry Reference]
1,3-Cyclohexanedione, 2-methyl-(1193-55-1) |
| Hazard Information | Back Directory | [Description]
2-methyl-1,3-Cyclohexanedione is a synthetic intermediate useful for pharmaceutical synthesis. | [Chemical Properties]
White to salmon powder | [Uses]
2-Methylcyclohexane-1,3-dione acts as a synthetic intermediate. It is an important starting material, exemplified in a formal synthesis of acorone. It is also used in Organic Synthesis, Pharmaceuticals, Agrochemicals. | [Uses]
An important starting material, exemplified in a formal synthesis of acorone.1 | [Synthesis]
In a reactor equipped with a stirrer, 300 parts of methanol, 56 parts of a 50% aqueous solution of dimethylamine and 56 parts of 1,3-cyclohexanedione were added and the mixture was warmed up to 30 °C. A 37% aqueous solution of formaldehyde was added dropwise over a period of 1 hour. After addition, the reaction solution was maintained at 40°C for 3 hours. The unreacted 1,3-cyclohexanedione content was monitored by HPLC to confirm the reaction endpoint. Subsequently, 10 portions of 5% palladium-carbon catalyst were added to the reaction mixture and the reaction was carried out at 30°C and atmospheric pressure with hydrogen gas passed for 15 hours. The unreacted 2-dimethylaminomethyl-1,3-cyclohexanedione content was detected by high performance liquid chromatography to confirm the completion of the reaction. At the end of the reaction, the catalyst was removed by filtration at 30 °C, 300 parts of water were added to the filtrate, methanol was removed by distillation, and the residue was adjusted with 35% hydrochloric acid to pH 6. The precipitate was collected by filtration, washed with water and dried at 70 °C to give 54.8 parts of 2-methyl-1,3-cyclohexanedione as dry cake (yield: 87.0%). HPLC analysis showed that the purity of 2-methyl-1,3-cyclohexanedione in the dry cake was 97.2%. The melting point of the dried cake was 206°-208°C (literature value: 207°-209°C). FD-MS analysis showed that the dried cake had a peak at m/z 126, which was consistent with the theoretical molecular weight. | [References]
[1] Patent: US5276198, 1994, A |
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