(1alpha,2alpha,4alpha)-1,2,4-Cyclohexanetricarboxylic acid
[CAS# 76784-95-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: (1alpha,2alpha,4alpha)-1,2,4-Cyclohexanetricarboxylic acid
• Synonyms: (1S,2R,4R)-cyclohexane-1,2,4-tricarboxylic acid
• Molecular Formula: C₉H₁₂O₆
• Molecular Weight: 216.19
• CAS Registry Number: 76784-95-7
• EC Number: 680-210-2
• SMILES: C1C[C@@H]([C@@H](C[C@@H]1C(=O)O)C(=O)O)C(=O)O

Properties

• Solubility: Soluble (61 g/L) (25 ºC), Calc.^*
• Density: 1.509±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 168-172 ºC^**
• Index of Refraction: 1.555, Calc.^*
• Boiling Point: 470.1±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 252.2±25.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Isoda, Sumiro; Chemical & Pharmaceutical Bulletin 1980, V28(8), P2337-46.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

(1alpha,2alpha,4alpha)-1,2,4-Cyclohexanetricarboxylic acid is a cyclic compound with three carboxyl groups attached to a cyclohexane ring. The structure of this compound consists of a six-membered cyclohexane ring with three carboxylic acid groups at the 1, 2, and 4 positions of the ring. This chemical substance has garnered interest in various fields due to its unique molecular structure and the potential applications that it offers in organic chemistry and material science.

The discovery of (1alpha,2alpha,4alpha)-1,2,4-cyclohexanetricarboxylic acid can be traced back to studies on cyclohexane derivatives, particularly those that involve functional groups such as carboxylic acids. Research on cyclohexane-based compounds has been ongoing for many years, with the goal of developing materials that exhibit specific properties such as enhanced stability, solubility, and reactivity. The incorporation of three carboxyl groups into a cyclohexane ring provides a structure that can participate in various chemical reactions, making it an interesting compound for synthesis and industrial applications.

One of the primary applications of (1alpha,2alpha,4alpha)-1,2,4-cyclohexanetricarboxylic acid is in the field of organic synthesis, where it is used as an intermediate in the preparation of various compounds. The carboxyl groups attached to the cyclohexane ring allow for a wide range of chemical modifications, including esterification, amidation, and metal complexation. These reactions make the compound a versatile building block in the synthesis of more complex molecules that can be used in pharmaceuticals, agrochemicals, and other specialized materials.

In particular, (1alpha,2alpha,4alpha)-1,2,4-cyclohexanetricarboxylic acid is used in the preparation of metal-organic frameworks (MOFs), which are materials that have gained significant attention for their applications in gas storage, catalysis, and separation processes. The presence of carboxyl groups in the molecule allows it to coordinate with metal ions, forming stable complexes that can be used to create MOFs with specific properties. These materials are highly porous and can be tailored for a variety of uses, including in the capture of greenhouse gases, such as carbon dioxide, or in the storage of hydrogen and other gases.

Furthermore, (1alpha,2alpha,4alpha)-1,2,4-cyclohexanetricarboxylic acid is also used in the field of polymer chemistry. By reacting with other monomers, it can form copolymers that have improved mechanical properties, thermal stability, and resistance to chemical degradation. These copolymers can be used in applications ranging from packaging materials to automotive components, where durability and performance are essential.

In addition to its applications in materials science, the compound has potential uses in the field of pharmaceuticals. The three carboxyl groups on the cyclohexane ring enable the compound to interact with biological systems in various ways. For example, it can act as a ligand for metal ions in biological environments, potentially influencing the activity of metal-dependent enzymes. As such, researchers are exploring its potential as a therapeutic agent or as a part of drug delivery systems.

The compound also holds promise in the agricultural sector, where it can be utilized in the design of new pesticides or herbicides. The ability to modify the structure of (1alpha,2alpha,4alpha)-1,2,4-cyclohexanetricarboxylic acid allows for the development of molecules that can specifically target pests or undesirable plant growth while minimizing environmental impact.

In conclusion, (1alpha,2alpha,4alpha)-1,2,4-cyclohexanetricarboxylic acid is a versatile chemical compound with a broad range of applications in organic synthesis, materials science, pharmaceuticals, and agriculture. Its unique structure and reactivity make it a valuable building block for the creation of new materials and molecules with tailored properties, and ongoing research continues to uncover additional uses for this important chemical substance.