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| | 1,1-Cyclopropanedicarboxylic acid monomethyl ester Basic information |
| Product Name: | 1,1-Cyclopropanedicarboxylic acid monomethyl ester | | Synonyms: | Cyclopropane-1,1-dicarboxylic acid Monoethyl ester;Cyclopropane-1,1-dicarboxylicacid,Methy;CYCLOPROPANE-1,1-DICARBOXYLIC ACID, METHYL ESTER;1,1-CYCLOPROPANEDICARBOXYLIC ACID MONOMETHYL ESTER;1,1-CYCLOPROPANEDICARBOXYLIC ACID-1-METHYL ESTER;1,1-Cyclopropanedicarboxylicacid,monomethylester(9CI);Cyclopropane-1,1-dicarboxylic acid monomethyl ester, 97%;1,1-Cyclopropanedicarboxylic acid-1-methyl e | | CAS: | 113020-21-6 | | MF: | C6H8O4 | | MW: | 144.13 | | EINECS: | | | Product Categories: | CARBOXYLICESTER;API intermediates | | Mol File: | 113020-21-6.mol |  |
| | 1,1-Cyclopropanedicarboxylic acid monomethyl ester Chemical Properties |
| Melting point | 47-51°C | | Boiling point | 85-87°C/0.2mm | | density | 1.419 | | Fp | 104 °C | | storage temp. | Sealed in dry,Room Temperature | | form | crystalline solid | | pka | 3.37±0.20(Predicted) | | color | White | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C6H8O4/c1-10-5(9)6(2-3-6)4(7)8/h2-3H2,1H3,(H,7,8) | | InChIKey | IZYOHLOUZVEIOS-UHFFFAOYSA-N | | SMILES | C1(C(O)=O)(C(OC)=O)CC1 |
| Hazard Codes | Xi,T | | Risk Statements | 25-52 | | Safety Statements | 45 | | RIDADR | UN2811 | | HazardClass | IRRITANT | | HS Code | 2917200090 |
| | 1,1-Cyclopropanedicarboxylic acid monomethyl ester Usage And Synthesis |
| Uses | 1,1-Cyclopropanedicarboxylic acid monomethyl ester is used as a pharmaceutical intermediate. | | Synthesis | 1. KOH (42 mg, 0.75 mmol) was added to a methanolic solution of dimethyl cyclopropane-1,1-dicarboxylate (100 mg, 0.63 mmol).
2. The reaction mixture was stirred at room temperature for 4 hours.
3. After completion of the reaction, the solvent was removed by concentration under reduced pressure.
4. The residue was diluted with water and acidified with concentrated hydrochloric acid to pH<2.
5. The acidified aqueous phase was extracted with dichloromethane (3 x 10 mL).
6. The organic phases are combined and dried over anhydrous sodium sulfate.
7. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give cyclopropane-1,1-dicarboxylic acid monomethyl ester (65 mg, 71% yield) as a white solid. | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2188 - 2193
[2] Patent: US2009/239848, 2009, A1. Location in patent: Page/Page column 33
[3] Patent: WO2012/74761, 2012, A1. Location in patent: Page/Page column 20-21
[4] Organic Letters, 2011, vol. 13, # 16, p. 4180 - 4183
[5] Patent: EP1577301, 2005, A1. Location in patent: Page/Page column 148 |
| | 1,1-Cyclopropanedicarboxylic acid monomethyl ester Preparation Products And Raw materials |
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