| Identification | Back Directory | [Name]
1,1-Cyclopropanedicarboxylic acid monomethyl ester | [CAS]
113020-21-6 | [Synonyms]
Cyclopropane-1,1-dicarboxylicacid,Methy
1,1-Cyclopropanedicarboxylic acid-1-methyl e
1-(methoxycarbonyl)cyclopropanecarboxylic acid
CYCLOPROPANE-1,1-DICARBOXYLIC ACID, METHYL ESTER
1,1-CYCLOPROPANEDICARBOXYLIC ACID-1-METHYL ESTER
1-(Methoxycarbonyl)cyclopropane-1-carboxylic acid
Cyclopropane-1,1-dicarboxylic acid Monoethyl ester
1,1-CYCLOPROPANEDICARBOXYLIC ACID MONOMETHYL ESTER
1,1-Cyclopropanedicarboxylicacid,monomethylester(9CI)
Cyclopropane-1,1-dicarboxylic acid monomethyl ester, 97% | [Molecular Formula]
C6H8O4 | [MDL Number]
MFCD06800496 | [MOL File]
113020-21-6.mol | [Molecular Weight]
144.13 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [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 |
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