1-Chloropyrrolo[1,2-a]pyrazine
[CAS# 136927-64-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 1-Chloropyrrolo[1,2-a]pyrazine
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• CAS Registry Number: 136927-64-5
• EC Number: 866-397-5
• SMILES: C1=CN2C=CN=C(C2=C1)Cl

Properties

• Density: 1.35±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.653, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-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.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1-Chloropyrrolo[1,2-a]pyrazine is a notable compound in the realm of heterocyclic chemistry, characterized by a fused bicyclic structure consisting of a pyrrole and a pyrazine ring, with a chlorine substituent at the 1-position. Its molecular formula is C7H6ClN2, and its unique structural attributes have drawn attention for various applications, particularly in medicinal chemistry and material science.

The discovery of 1-chloropyrrolo[1,2-a]pyrazine emerged from the systematic exploration of substituted pyrrole and pyrazine derivatives, which have long been recognized for their diverse biological activities. Researchers sought to synthesize compounds that could potentially interact with a range of biological targets while also possessing favorable pharmacological profiles. The incorporation of a chlorine atom into the structure not only enhances the compound's reactivity but also introduces specific electronic properties that can influence its biological activity.

One significant application of 1-chloropyrrolo[1,2-a]pyrazine is its role as a precursor in the synthesis of bioactive molecules. The chlorine atom serves as a versatile handle for further chemical modifications, allowing researchers to create a library of derivatives with varied biological activities. These derivatives can be screened for potential therapeutic effects, particularly against diseases such as cancer, inflammation, and bacterial infections. The unique bicyclic framework of 1-chloropyrrolo[1,2-a]pyrazine contributes to its potential as a pharmacophore in drug design.

In addition to its medicinal applications, 1-chloropyrrolo[1,2-a]pyrazine is being investigated for its utility in materials science. The compound’s ability to form conjugated systems makes it a candidate for the development of organic electronic materials. Researchers are exploring the optoelectronic properties of compounds based on the pyrrolo[1,2-a]pyrazine structure, with applications in organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The presence of the chlorine substituent may enhance the solubility and stability of these materials, further promoting their use in practical applications.

Moreover, 1-chloropyrrolo[1,2-a]pyrazine has been the subject of studies aimed at understanding its mechanism of action at a molecular level. Investigating how this compound interacts with biological macromolecules, such as proteins and nucleic acids, is crucial for elucidating its potential therapeutic pathways. This understanding can facilitate the rational design of more effective analogs and provide insights into the development of new therapeutic strategies.

In summary, 1-chloropyrrolo[1,2-a]pyrazine is a significant compound with a promising future in both medicinal chemistry and materials science. Its unique bicyclic structure, combined with the presence of a chlorine substituent, offers numerous opportunities for further exploration and development. As research progresses, this compound is expected to play a vital role in the discovery of new therapeutic agents and innovative materials.

References

2021. Buchwald-Hartwig reaction: an update. Monatshefte für Chemie - Chemical Monthly, 152(10).
DOI: 10.1007/s00706-021-02834-3