2,3-Pyrazinecarboxylic anhydride
[CAS# 4744-50-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2,3-Pyrazinecarboxylic anhydride
• Synonyms: Furo[3,4-b]pyrazine-5,7-dione
• Molecular Formula: C₆H₂N₂O₃
• Molecular Weight: 150.09
• CAS Registry Number: 4744-50-7
• EC Number: 225-260-4
• SMILES: C1=CN=C2C(=N1)C(=O)OC2=O

Properties

• Melting point: 210 ºC (dec.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2,3-Pyrazinecarboxylic anhydride is a significant compound in the field of organic chemistry, characterized by its unique chemical structure and potential applications in various industrial and research areas. This compound is an anhydride derived from 2,3-pyrazinecarboxylic acid, featuring a cyclic structure with an anhydride functional group. Its synthesis and utility have garnered considerable interest due to its distinct properties and reactivity.

The discovery of 2,3-pyrazinecarboxylic anhydride can be traced back to efforts in organic synthesis aimed at exploring the reactivity and utility of pyrazine derivatives. Pyrazinecarboxylic acids and their anhydrides have been studied for their potential applications in pharmaceuticals, agrochemicals, and materials science. The anhydride form of 2,3-pyrazinecarboxylic acid was developed through a process that typically involves the dehydration of the corresponding carboxylic acid. This dehydration can be achieved using various dehydrating agents, resulting in the formation of the anhydride.

The primary application of 2,3-pyrazinecarboxylic anhydride lies in its role as a reagent in organic synthesis. Its reactivity as an anhydride makes it valuable for introducing pyrazinecarboxyl groups into various molecules. This application is particularly relevant in the synthesis of complex organic compounds where pyrazine functionalities are required. The anhydride can react with nucleophiles, such as alcohols or amines, to form esters or amides, respectively. These reactions are crucial in the development of pharmaceuticals and other bioactive compounds.

In the pharmaceutical industry, 2,3-pyrazinecarboxylic anhydride has been explored for its potential role in the synthesis of bioactive molecules. The ability to modify pyrazine structures by incorporating different functional groups via anhydride reactions can lead to the development of new drugs with enhanced efficacy or novel mechanisms of action. Researchers have investigated its use in synthesizing compounds with potential antimicrobial, antiviral, or anticancer properties.

In addition to its pharmaceutical applications, 2,3-pyrazinecarboxylic anhydride is also used in materials science. The compound can serve as a precursor for the synthesis of polymeric materials and advanced materials with specific properties. For instance, it may be used in the preparation of pyrazine-containing polymers or as a building block for creating materials with unique electronic or optical properties.

The synthesis of 2,3-pyrazinecarboxylic anhydride involves several key steps, including the preparation of the starting pyrazinecarboxylic acid and its subsequent dehydration. This process requires precise control of reaction conditions to ensure the formation of the anhydride with high purity and yield. The resulting compound is then characterized using techniques such as spectroscopy and chromatography to confirm its structure and quality.

In summary, 2,3-pyrazinecarboxylic anhydride is an important compound in organic chemistry with diverse applications in pharmaceuticals and materials science. Its reactivity as an anhydride makes it a valuable reagent for the synthesis of various bioactive and functionalized compounds. Ongoing research continues to explore its full range of applications and potential in developing new materials and therapeutic agents.