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ChemicalBook--->CAS DataBase List--->1461-96-7

1461-96-7

1461-96-7 Structure

1461-96-7 Structure
IdentificationBack Directory
[Name]

CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID
[CAS]

1461-96-7
[Synonyms]

cis-Cyclopentanedicarboxylic acid
cis-Cyclopentane-1,2-dicarboxylic
CIS-1,2-CYCLOPENTANEDICARBOXYLIC ACID
CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID
1,2-Cyclopentanedicarboxylic acid, cis-
(±)-cis-Cyclopentane-1,2-dicarboxylicaci
(1R)-Cyclopentane-1β,2β-dicarboxylic acid
(1R,2S)-1,2-Cyclopentanedicarboxylic acid
(1R,2S)-cyclopentane-1,2-dicarboxylic acid
(+/-)-cis-Cyclopentane-1,2-dicarboxylic acid
rel-(1R,2S)-1,2-Cyclopentanedicarboxylic acid
(1R,2S)-rel-1,2-Cyclopentanedicarboxylic Acid
rel-(1R,2S)-cyclopentane-1,2-dicarboxylic acid
1,2-Cyclopentanedicarboxylic acid, (1R,2S)-rel-
TIANFU-CHEM - CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID
(+/-)-cis-Cyclopentane-1,2-dicarboxylic acid >=97.0% (GC)
[Molecular Formula]

C7H10O4
[MDL Number]

MFCD01311172
[MOL File]

1461-96-7.mol
[Molecular Weight]

158.15
Chemical PropertiesBack Directory
[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 DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/38
[Safety Statements ]

26
[WGK Germany ]

3
Hazard InformationBack Directory
[Uses]

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

Possible inhibitor of prolidase.
[Synthesis]

Ethyl 2-oxocyclohexanecarboxylate

1655-07-8

CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID

1461-96-7

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
Spectrum DetailBack Directory
[Spectrum Detail]

CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID(1461-96-7)1HNMR
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