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| | 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester Basic information |
| Product Name: | 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester | | Synonyms: | DIMETHYL 1,4-CYCLOHEXANEDIONE-2,5-DICARBOXYLATE;DIMETHYL 2,5-DIOXO-1,4-CYCLOHEXANEDICARBOXYLATE;DIMETHYL 2,5-DIOXOCYCLOHEXANE-1,4-DICARBOXYLATE;SUCCINYLOSUCCINIC ACID DIMETHYL ESTER;2,5-DIOXO-1,4-CYCLOHEXANEDICARBOXYLIC ACID DIMETHYL ESTER;1,4-CYCLOHEXANEDIONE-2,5-DICARBOXYLIC ACID DIMETHYL ESTER;1,4-CYCLOHEXANEDICARBOXYLIC ACID, 2,5-DIOXO, DIMETHYL ESTER;4-cyclohexanedicarboxylicacid,2,5-dioxo-dimethylester | | CAS: | 6289-46-9 | | MF: | C10H12O6 | | MW: | 228.2 | | EINECS: | 228-528-9 | | Product Categories: | Pharmaceutical Intermediates;Pharmaceutical Intermediate | | Mol File: | 6289-46-9.mol |  |
| | 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester Chemical Properties |
| Melting point | 154-157 °C | | Boiling point | 330°C (rough estimate) | | density | 1.3792 (rough estimate) | | vapor pressure | 0-0.002Pa at 20-50℃ | | refractive index | 1.6000 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | form | Fine Crystalline Powder | | pka | 9.04±0.40(Predicted) | | color | White to light yellow-green | | Water Solubility | Soluble in water 0.0016 g/L. | | InChI | InChI=1S/C10H12O6/c1-15-9(13)5-3-8(12)6(4-7(5)11)10(14)16-2/h5-6H,3-4H2,1-2H3 | | InChIKey | MHKKFFHWMKEBDW-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)CC(=O)C(C(OC)=O)CC1=O | | LogP | 2.49 at 23℃ and pH7 | | CAS DataBase Reference | 6289-46-9(CAS DataBase Reference) | | EPA Substance Registry System | 1,4-Cyclohexanedicarboxylic acid, 2,5-dioxo-, 1,4-dimethyl ester (6289-46-9) |
| | 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester Usage And Synthesis |
| Chemical Properties | white to light yellow-green fine cryst. powder | | Uses | Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate is used in the production of pigments such as pigment red 122 and pigment violet 19. It also can react with 2,4-diamino-phenol to get 2,5-bis-(3-amino-4-hydroxy-phenylamino)-cyclohexa-1,4-diene-1,4-dicarboxylic acid dimethyl ester. | | Synthesis | General procedure for the synthesis of dimethyl succinosuccinate from methyl 4-chloroacetoacetate: Under stirring conditions, methyl 4-chloroacetoacetate (10 g, 0.06 mol) was slowly added to a mixed solution containing potassium carbonate (17 g, 0.12 mol) and DMSO (50 mL). The reaction mixture was first stirred at room temperature for 3 hours, then warmed to 60 °C and continued stirring for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with an appropriate amount of water and subsequently filtered. The filtrate was extracted with ether and the extract was dried over anhydrous magnesium sulfate and the solvent was removed by distillation to give a yellow crystal product (14 g, 52% yield) with a melting point of 152-153 °C. The structure of the product was confirmed by 1H NMR and 13C NMR spectra: 1H NMR (δ, ppm): 3.20 (s, 2H, CH2), 3.80 (s, 3H, CH3O), 3.90 (s, 3H, CH3O), 7.45 (s, 1H, CH=), 9.80 (s, 1H, OH), 12.10 (s, 1H, OH). 13C NMR (CDCl3, δ, ppm): 28.42, 52.33, 53.07, 95.94, 118.00, 120.05, 151.32, 168.00, 171.36. Elemental analytical results are in accordance with the theoretical values: measured (%): C 52.78, H 5.17; theoretical (C10H12O6, %): C 52.63, H 5.26. | | References | [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 1099 - 1101
[2] Zh. Org. Khim., 2017, vol. 53, # 7, p. 1084 - 1086,3 |
| | 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester Preparation Products And Raw materials |
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