2-Cyanopyrimidine
[CAS# 14080-23-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Cyanopyrimidine
• Name: 2-Cyanopyrimidine
• Synonyms: 2-Pyrimidinecarbonitrile
• Molecular Formula: C₅H₃N₃
• Molecular Weight: 105.10
• CAS Registry Number: 14080-23-0
• EC Number: 604-202-5
• SMILES: C1=CN=C(N=C1)C#N

Properties

• Melting point: 40-44 °C
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H317
• Safety Statements: P261-P264-P270-P272-P280-P301+P316-P302+P352-P321-P330-P333+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Cyanopyrimidine is a heterocyclic organic compound with a pyrimidine ring substituted by a cyano group at the second position. It belongs to the family of nitrile-containing heterocycles, which are widely used as intermediates in the synthesis of more complex molecules. The discovery of 2-cyanopyrimidine can be traced to early studies on nitrogen-containing heterocycles, where the introduction of functional groups like nitriles was explored for enhancing the reactivity and versatility of these compounds in chemical transformations.

The structure of 2-cyanopyrimidine is based on a six-membered ring consisting of four carbon atoms and two nitrogen atoms at positions 1 and 3, characteristic of pyrimidine. The nitrile (-C≡N) group attached to the second carbon in the ring plays a crucial role in the reactivity of this molecule. This functional group increases the electrophilicity of the pyrimidine ring, making it a useful intermediate in organic synthesis. Its ability to participate in various chemical reactions makes it an attractive building block for the synthesis of pharmaceuticals, agrochemicals, and other biologically active compounds.

In medicinal chemistry, 2-cyanopyrimidine has gained attention due to its role as a scaffold in the development of drugs and enzyme inhibitors. Pyrimidine derivatives, including those with cyano groups, are often used as core structures in the design of antitumor, antiviral, and antibacterial agents. The nitrile group in 2-cyanopyrimidine can undergo further chemical modifications to introduce various pharmacophoric groups, enhancing the compound's activity and selectivity against biological targets. As a result, 2-cyanopyrimidine derivatives have been studied for their potential in cancer treatment and as inhibitors of kinases and other enzymes critical for disease processes.

In addition to pharmaceutical applications, 2-cyanopyrimidine is used as an intermediate in the synthesis of dyes, pigments, and other fine chemicals. Its reactive nitrile group makes it suitable for nucleophilic substitution, reduction, and cyclization reactions, allowing for the construction of a wide variety of heterocyclic compounds. These reactions are particularly valuable in the preparation of advanced materials and specialty chemicals that find use in electronics, coatings, and polymer industries.

The compound is also employed in the field of agrochemicals, where pyrimidine derivatives have shown efficacy as herbicides, fungicides, and insecticides. 2-Cyanopyrimidine can serve as a precursor for the synthesis of biologically active compounds that target specific enzymes or receptors in plants and pests, contributing to more effective and sustainable agricultural practices.

Safety considerations are important when handling 2-cyanopyrimidine, as the compound can be harmful if inhaled or absorbed through the skin. Appropriate safety measures, such as using protective equipment and working in a well-ventilated area, should be followed to minimize exposure.

In summary, 2-cyanopyrimidine is a versatile compound that plays a significant role in organic synthesis and drug development. Its applications in pharmaceuticals, agrochemicals, and materials science highlight its importance as a building block for designing biologically active and industrially relevant compounds.

References

2023. Computational studies of closely related 2-cyanopyrimidine, pyrimidine-2-carboximidamide and 2,4,6-tris(2-pyrimidyl)-1,3,5-triazine with a potency against SARS-CoV-2. Monatshefte fÜr Chemie - Chemical Monthly, 154(12), 1399-1411.
DOI: 10.1007/s00706-023-03133-9

2023. Synthesis and Antimicrobial Activity of Some New Pyrimidine Nucleosides and Their Analogs. Russian Journal of Organic Chemistry, 59(1), 165-173.
DOI: 10.1134/s1070428023010116

1956. Heteroarylierungen mit quartärsubstituierten Pyrimidinsalzen. Monatshefte fÜr Chemie, 87(5), 708-717.
DOI: 10.1007/bf00917846