1,1-Cyclopropanedicarboxylic acid monomethyl ester Chemical Properties

Melting point:

47-51°C

Boiling point:

85-87°C/0.2mm

Density 

1.419

Flash point:

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

Safety Information

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(113020-21-6)Related Product Information

• Folic acid
• Methyl 2-iodobenzoate
• Methyl formate
• Methyl acrylate
• Tris(trimethylsilyl)phosphate
• Methyl benzoate
• Methylparaben
• Cyclopropane
• Methyl anthranilate
• Olibanum oil
• BUTYL OLEATE
• Dimethyl succinate
• Trimethoxymethane
• Citric acid
• Ascoric Acid
• Diethyl 1,1-cyclopropanedicarboxylate
• 1,1-CYCLOPROPANEDICARBOXYLIC ACID MONOETHYL ESTER
• Methyl chloroformate