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| | 2,4-Dibromoglutaric acid dimethyl ester Basic information |
| Product Name: | 2,4-Dibromoglutaric acid dimethyl ester | | Synonyms: | Pentanedioic acid, 2,4-dibromo-, dimethyl ester;Pentanedioic acid, 2,4-dibromo-, 1,5-dimethyl ester;1,5-dimethyl 2,4-dibromopentanedioate;2,4-Dibromo-Pentanedioic Acid Dimethyl Ester(WX630083);2,4-Dibromoglutaric acid dimethyl ester;2,4-Dibromopentanedioic acid 1,5-dimethyl ester;Dimethyl 2,4-dibromoglutarate;Dimethyl 2,4-dibromopentanedioate | | CAS: | 869-09-0 | | MF: | C7H10Br2O4 | | MW: | 317.96 | | EINECS: | | | Product Categories: | | | Mol File: | 869-09-0.mol |  |
| | 2,4-Dibromoglutaric acid dimethyl ester Chemical Properties |
| Melting point | 45 °C | | Boiling point | 151-153 °C(Press: 11 Torr) | | density | 1.7612 g/cm3 | | storage temp. | Sealed in dry,Room Temperature | | Appearance | Pink to red Liquid | | InChI | InChI=1S/C7H10Br2O4/c1-12-6(10)4(8)3-5(9)7(11)13-2/h4-5H,3H2,1-2H3 | | InChIKey | ZBBXTTCCOXKVJB-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C(Br)CC(Br)C(OC)=O |
| | 2,4-Dibromoglutaric acid dimethyl ester Usage And Synthesis |
| Synthesis | The general procedure for the synthesis of dimethyl cis-azetidine-2,4-dicarboxylate (CAS:31358-13-1) from 2,4-dibromopentanedioic acid is as follows:
Example 3: Preparation of dimethyl cis-azetidine-2,4-dicarboxylate
1. 1.14 g (3.93 mmol) of 2,4-dibromopentanedioic acid, 1 mL of methanol, 1.2 mL of carbon tetrachloride (CCl4), and 1 drop of concentrated hydrochloric acid were mixed.
2. The reaction mixture was refluxed in the presence of sulfuric acid for 8 hours.
3. Upon completion of the reaction, an aqueous post-treatment is performed: extraction with dichloromethane (CH2Cl2) and saturated sodium bicarbonate (NaHCO3) solution.
4. The organic phase was filtered through a silica gel column and the solvent was evaporated to give 0.87 g (70% yield) of dimethyl 2,4-dibromoglutarate.
Product characterization data:
1H NMR (CDCl3): δ 3.82 (s, 6H); dl-isomer: δ 4.53 (dd, 2H, J = 6.5, 8 Hz), 2.68 (dd, 2H, J = 6.5, 8 Hz); endo isomer: δ 4.41 (t, 2H, J = 7.5 Hz), 2.89 (dt, 1H, J = 7.5 (t), 14.5 (d Hz), 2.64 (dt, 1H, J = 7.5(t), 14.5(d)Hz); dl/meso = 3:1.
IR (neat, cm-1): 3004, 2955, 1740, 1437, 1300, 1267, 1215, 1156, 851. | | References | [1] Patent: US4946839, 1990, A
[2] Patent: US4990504, 1991, A |
| | 2,4-Dibromoglutaric acid dimethyl ester Preparation Products And Raw materials |
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