CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID Chemical Properties

Melting point:

132-136℃

Boiling point:

378.6±35.0 °C(Predicted)

Density 

1.396±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Store at room temperature

solubility 

Chloroform, Methanol, Moderately Solubility in Water

form 

crystals

pka

pK1:4.43;pK2:6.67 (25°C)

Appearance

White to off-white Solid

BRN 

2049007

InChI

InChI=1/C7H10O4/c8-6(9)4-2-1-3-5(4)7(10)11/h4-5H,1-3H2,(H,8,9)(H,10,11)/t4-,5+

InChIKey

ASJCSAKCMTWGAH-SYDPRGILSA-N

SMILES

[C@@H]1(C(O)=O)CCC[C@@H]1C(O)=O |&1:0,7,r|

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

3

CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID Usage And Synthesis

Uses

(1R,2S)-rel-1,2-Cyclopentanedicarboxylic Acid is a Possible inhibitor of prolidase.

Synthesis

The general procedure for the synthesis of cis-1,2-cyclopentanedicarboxylic acid from ethyl 2-oxocyclohexanecarboxylate was as follows: bromine (112.8 g, 705.6 mmol) was slowly added dropwise to a solution of ethyl 2-oxocyclohexanecarboxylate (120 g, 705.6 mmol) dissolved in chloroform (360 ml) at 0 °C. The reaction mixture was stirred at room temperature overnight and then washed sequentially with sodium bicarbonate solution (2 x 200 ml) and brine (2 x 100 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated and the resulting residue was added slowly and dropwise to a pre-cooled aqueous solution of potassium hydroxide (168 g, 3 mol) (960 ml). The reaction mixture was continued to be stirred at 0 °C for 6 h and subsequently extracted with ether. The aqueous phase was adjusted to pH 5 with 4.0 M hydrochloric acid and extracted again with ether. All organic layers were combined, washed with brine (200 ml), dried, filtered and concentrated to give a yellow oil. The oil was crystallized by mixed solvent ethyl acetate/ether to give cis-1,2-cyclopentanedicarboxylic acid as colorless crystals (70 g, 63% yield). Mass spectrum (electrospray ionization): 159 [M + H]+.

References

[1] Tetrahedron Letters, 2007, vol. 48, # 4, p. 635 - 638
[2] Patent: WO2013/95275, 2013, A1. Location in patent: Page/Page column 35
[3] Journal of the American Chemical Society, 2000, vol. 122, # 50, p. 12610 - 12611
[4] Journal of Organic Chemistry, 1989, vol. 54, # 4, p. 817 - 824
[5] Journal of Organic Chemistry, 1961, vol. 26, p. 22 - 27

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