1,1-Cyclopropanedicarboxylic acid Chemical Properties

Melting point:

134-136 °C(lit.)

Boiling point:

200.75°C (rough estimate)

Density 

1.3985 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: soluble1g/10 mL, clear, colorless

pka

1.82(at 25℃)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Soluble

BRN 

1864823

InChI

InChI=1S/C5H6O4/c6-3(7)5(1-2-5)4(8)9/h1-2H2,(H,6,7)(H,8,9)

InChIKey

FDKLLWKMYAMLIF-UHFFFAOYSA-N

SMILES

C1(C(O)=O)(C(O)=O)CC1

CAS DataBase Reference

598-10-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34

Safety Statements 

26-36-45-36/37/39

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29172090

MSDS

• Language:English Provider:1,1-Cyclopropanedicarboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,1-Cyclopropanedicarboxylic acid Usage And Synthesis

Chemical Properties

white to almost white crystalline powder

Uses

1,1-Cyclopropanedicarboxylic acid, is used as an inhibitor of 1-aminocyclopropane-1-carboxylic acid oxidase, was quantitated in Lycopersicum esculentum by HPLC-electrospray tandem mass spectrometry. Crystal and molecular structure of cyclopropane-1,1-dicarboxylic acid has been reported. Cyclopropane-1,1-dicarboxylic acid was used in the preparation of new heterocyclic derivatives of cyclopropane dicarboxylic acid containing thiadiazole and 1,2,4-triazole moieties. It was also used to prepare spiro-cyclopropyl metallocycles. It can also be used as a building block for the synthesis of a series of cyclopropanecarboxamides, having antifungal activity.

Uses

1,1-Cyclopropanedicarboxylic acid is used to prepare spiro-cyclopropyl metallocycles.1

General Description

Cyclopropane-1,1-dicarboxylic acid is a dicarboxylic acid. Cyclopropane-1,1-dicarboxylic acid, an inhibitor of 1-aminocyclopropane-1-carboxylic acid oxidase, was quantitated in Lycopersicum esculentum by HPLC-electrospray tandem mass spectrometry. Crystal and molecular structure of cyclopropane-1,1-dicarboxylic acid has been reported.

Synthesis

GENERAL STEPS: 15 g of diethyl malonate was dissolved in 187 ml of aqueous solution containing 50 μl NaOH at room temperature. Subsequently 21.3 g (93.8 mmol) of benzyltriethylammonium chloride was added and the resulting mixture was stirred for 10 minutes. To the reaction solution was added 12.3 g (65.47 mmol) of 1,2-dibromoethane and the reaction mixture continued to be stirred at room temperature for more than 18 hours. Upon completion of the reaction, the reaction mixture was neutralized by adding acid solution dropwise. The reaction mixture was washed with aqueous sulfuric acid solution and subsequently extracted with ethyl acetate. The organic phases were combined and the solvent was removed by distillation under reduced pressure to afford 6.2 g of a white solid product, 1,1-cyclopropanedicarboxylic acid, in 76.1% yield.

Purification Methods

Recrystallise the di-acid from CHCl3, EtOAc or *C6H6/Et2O/pet ether. It forms a monohydrate. [Nicolet & Satler J Am Chem Soc 49 2070 1927, Beilstein 9 II 512, 9 III 3795.]

References

[1] Organic Letters, 2015, vol. 17, # 11, p. 2618 - 2621
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3353 - 3358
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6674 - 6679
[4] Mendeleev Communications, 2014, vol. 24, # 6, p. 345 - 345
[5] Patent: WO2005/79812, 2005, A1. Location in patent: Page/Page column 51

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