1,2-Cyclopentanedicarboxylic acid
[CAS# 50483-99-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 1,2-Cyclopentanedicarboxylic acid
• Synonyms: NSC 139994
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• CAS Registry Number: 50483-99-3
• EC Number: 633-363-4
• SMILES: C1CC(C(C1)C(=O)O)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 161-162 ºC
• Index of Refraction: 1.535, Calc.^*
• Boiling Point: 378.6±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 196.9±22.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H315-H318-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

1,2-Cyclopentanedicarboxylic acid is a chemical compound with a bicyclic structure, consisting of a five-membered cyclopentane ring with two carboxyl groups (-COOH) attached to the 1 and 2 positions. This compound is part of a class of chemicals known as dicarboxylic acids, which are important in organic chemistry due to their versatile reactivity and role as intermediates in various chemical processes.

The discovery of 1,2-cyclopentanedicarboxylic acid dates back to early studies on the synthesis of bicyclic carboxylic acids, where researchers were exploring new ways to modify the properties of organic acids by incorporating cyclic structures. Over time, the compound was recognized for its potential in diverse applications, particularly due to its ability to undergo a range of chemical reactions that are of interest to both industrial and academic chemists.

In organic synthesis, 1,2-cyclopentanedicarboxylic acid serves as an important intermediate in the preparation of various compounds. It can undergo a variety of reactions, including esterification, decarboxylation, and reduction, which are useful in the production of other chemical substances. The two carboxyl groups in the molecule make it an ideal candidate for cross-linking reactions, which are critical in the synthesis of polymers and other complex organic compounds. Additionally, the compound can be used to introduce functional groups into larger molecular structures, contributing to the creation of new materials with specific desired properties.

In the field of materials science, 1,2-cyclopentanedicarboxylic acid has been explored for its potential in the synthesis of biodegradable polymers. Polymers derived from dicarboxylic acids such as 1,2-cyclopentanedicarboxylic acid exhibit useful characteristics like improved flexibility, strength, and environmental compatibility. The compound has also been examined as a monomer in the production of copolymers, which find applications in packaging, coatings, and adhesives.

Furthermore, the compound has been studied for its potential as a precursor in the preparation of metal-organic frameworks (MOFs) and other coordination compounds. MOFs are a class of materials composed of metal ions coordinated to organic ligands, and they have garnered significant attention in recent years for their applications in gas storage, catalysis, and separation technologies. The carboxyl groups in 1,2-cyclopentanedicarboxylic acid provide a useful functional group for coordinating with metal centers, enabling the formation of stable and highly porous structures.

In addition to its synthetic and industrial uses, 1,2-cyclopentanedicarboxylic acid has also been of interest in the study of reaction mechanisms and catalysis. The compound’s unique structure allows it to participate in various catalytic reactions, particularly those involving metal catalysis, where the carboxylate group can interact with metal centers to facilitate reaction steps. This property has led to its exploration as a ligand in catalytic systems designed to promote organic transformations.

Overall, 1,2-cyclopentanedicarboxylic acid is a valuable compound in organic chemistry with applications ranging from the synthesis of polymers and materials to its role as a precursor in the preparation of coordination compounds and catalysts. Its versatile reactivity, due to the presence of two carboxyl groups on a bicyclic ring, makes it a key intermediate in the development of various chemical processes and materials. Further research and development in this area are likely to continue, leading to the discovery of additional uses for this important compound.

References

2018. Comprehensive optimization of precursor-directed production of BC194 by Streptomyces rochei MB037 derived from the marine sponge Dysidea arenaria. Applied Microbiology and Biotechnology, 102(20).
DOI: 10.1007/s00253-018-9237-5

2014. Safety Risk Categorization of Organic Extractables Associated with Polymers used in Packaging, Delivery and Manufacturing Systems for Parenteral Drug Products. Pharmaceutical Research, 31(11).
DOI: 10.1007/s11095-014-1523-z

2011. One-Dimensional Hydrogen-Bonded Infinite Chain from Nickel(II) Tetraaza Macrocyclic Complex and 1,2-Cyclopentanedicarboxylate Ligand. International Journal of Molecular Sciences, 12(4).
DOI: 10.3390/ijms12042232