2-Chloro-4-Pyridinecarboxylic Acid CAS 6313-54-8

2-Chloro-4-pyridinecarboxylic acid is an organic compound with CAS 6313-54-8 and chemical formula C6H4ClNO2. Usually white or light yellow powder with a slight irritating odor. Slightly soluble in water, slightly soluble in ethanol, insoluble in ether. Stable at room temperature, but may decompose under high temperature or exposure to light. The structure contains a free carboxyl unit and a chlorine atom. Due to the electron deficiency of the pyridine ring, this substance can undergo a series of nucleophilic substitution reactions under the attack of strong nucleophilic reagents, resulting in a series of dechlorinated functionalized products. It is a pyridine derivative that can combine with acidic substances to form salts. It can be used as an intermediate in organic synthesis and pharmaceutical chemistry, and is often used for structural modification and synthesis of drug molecules and bioactive molecules. For example, relevant literature has reported that this substance can be used in the synthesis of high camptothecin derivatives with anticancer activity.

2,6-Dichloroisoniacin is obtained through chlorination reaction, followed by chlorination reaction to obtain 2-chloroisoniacin, which is then synthesized through directed dechlorination reaction.

Step 1: Chlorination reaction to obtain 2,6-dichloroisononicotinic acid:

(1) Under appropriate reaction conditions, react isoniacin with chlorinating agents (such as sulfoxide chloride). The function of a chlorinating agent is to replace the hydrogen atom in isoniacin with the chlorine atom.

(2) After the reaction is completed, 2,6-dichloroisonotinic acid is obtained through appropriate separation and purification methods (such as distillation, crystallization, etc.). The product of this step is 2,6-dichloroisonotinic acid.

C₆H₃Cl₂NO₂ + HCl → 2,6-Dichloroisonicotinic acid hydrochloride

Step 2: Chlorination reaction to obtain 2-chloroisoniatinic acid:

(1) React the 2,6-dichloroisonotinic acid obtained in the previous step with a chlorinating agent again. This time, the action of the chlorinating agent is to selectively replace one chlorine atom in 2,6-dichloroisononicotinic acid with another chlorine atom, thereby forming 2-chloroisonicotinic acid.

(2) After the reaction is completed, 2-chloroisonicotinic acid is also obtained through appropriate separation and purification methods. The product of this step is 2-chloroisonicotinic acid.

2,6-Dichloroisoniazid hydrochloride + HCl → C₆H₄ClNO₂

Step 3: Preparation of 2-chloroisonicotinic acid through directed dechlorination reaction:

(1) React the 2-chloroisonicotinic acid obtained in the previous step with a directed dechlorination agent. The function of directional dechlorination agent is to selectively remove chlorine atoms from 2-chloroisoniacin, thereby obtaining the target product 2-chloroisoniacin.

(2) After the reaction is completed, pure 2-chloroisonicotinic acid is obtained through appropriate separation and purification methods. The product of this step is the target 2-Chloro-4-pyridinecarboxylic acid.

C₆H₄ClNO₂ + directional dechlorination agent → C₆H₄ClNO₂

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2-Chloro-4-pyridinecarboxylic acid has a wide range of applications in chemistry. The following is a detailed description of all its uses in chemistry:
1. Organic synthesis
It is an important intermediate in organic synthesis. It can participate in various organic reactions, such as esterification, amidation, alkylation, etc., thereby constructing various complex organic molecules. By transforming and modifying its functional groups, compounds with different structures and properties can be synthesized, providing rich synthesis routes and strategies for organic synthesis.
2. Analytical Chemistry
It also has applications in analytical chemistry. It can be used as a fluorescent probe, chromatographic separator, etc. for chemical analysis. For example, by utilizing the fluorescence properties of 2-Chloro 4-pyridinecarboxylic acid, highly sensitive fluorescent probes can be designed for detecting pollutants in the environment, metabolites in living organisms, and more. In addition, it can also serve as a chromatographic separation agent for the separation and analysis of complex samples.
3. Electrochemistry
It also has certain applications in the field of electrochemistry. It can be used as a battery material, capacitor material, etc. for electrochemical energy storage and conversion. For example, by utilizing the redox properties of 2-Chloro 4 pyridinecarboxylic acid, high-performance battery materials can be designed to improve the energy storage density and cycling stability of the battery. In addition, it can also be used to synthesize capacitor materials, improving the performance and service life of capacitors.

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