2-Bromopyrimidine
[CAS# 4595-60-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Bromopyrimidine
• Name: 2-Bromopyrimidine
• Molecular Formula: C₄H₃BrN₂
• Molecular Weight: 158.98
• CAS Registry Number: 4595-60-2
• EC Number: 224-993-7
• SMILES: C1=CN=C(N=C1)Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 55-57 °C (Expl.)
• Index of Refraction: 1.568, Calc.^*
• Boiling Point: 249.9±23.0 °C (760 mmHg), Calc.^*, 62-64 °C (1.5 mmHg) (Expl.)
• Flash Point: 105.0±22.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Bromopyrimidine is an organic compound with the chemical formula C4H3BrN2. It belongs to the family of halogenated heterocyclic compounds, specifically a bromopyrimidine derivative, where the bromine atom is attached to the second carbon of the pyrimidine ring. Pyrimidine derivatives, like 2-bromopyrimidine, are essential intermediates in the synthesis of various pharmaceuticals, agrochemicals, and biologically active molecules. The compound was first synthesized in the early 20th century and has since found extensive use in both research and industrial applications.

The discovery of 2-bromopyrimidine is part of a broader effort to explore and develop halogenated heterocycles due to their diverse reactivity profiles and ability to participate in various chemical transformations. It is typically synthesized through halogenation of pyrimidine or other pyrimidine derivatives using bromine or bromine-containing reagents. This process introduces the bromine atom selectively at the second position of the pyrimidine ring, providing a versatile building block for further synthetic modifications.

In terms of applications, 2-bromopyrimidine is widely used in organic synthesis as a key intermediate. The bromine atom at the C-2 position allows for a variety of subsequent reactions, such as nucleophilic substitution, cross-coupling reactions, and metal-catalyzed transformations. These reactions are valuable for the construction of complex organic molecules. One prominent use of 2-bromopyrimidine is in the synthesis of pyrimidine-based drugs, including antiviral and anticancer agents. The compound can serve as a starting material for the preparation of diverse pharmaceutical molecules by incorporating other functional groups into the pyrimidine ring or substituting the bromine atom with other atoms or groups.

Moreover, 2-bromopyrimidine is an important reagent in the development of agrochemicals. Its ability to participate in reactions such as Suzuki and Heck couplings allows for the creation of novel pesticidal and herbicidal compounds. The compound's role as an intermediate in the synthesis of more complex pyrimidine derivatives has contributed to the development of several agrochemicals that offer improved efficacy and selectivity in controlling pests and weeds.

The use of 2-bromopyrimidine extends beyond pharmaceuticals and agrochemicals to include materials science. It has been explored as a precursor for the synthesis of functionalized polymers and materials with electronic or optical properties. The halogenated nature of 2-bromopyrimidine makes it valuable in the preparation of compounds for use in optoelectronic devices, where specific molecular interactions are required.

In summary, 2-bromopyrimidine is a highly versatile compound with significant applications in organic synthesis, pharmaceuticals, agrochemicals, and materials science. Its ability to undergo a variety of chemical transformations has made it an essential intermediate in the development of novel molecules with important biological and industrial properties. As research continues, the utility of 2-bromopyrimidine in drug discovery, materials engineering, and other fields is likely to expand further.

References

2021. Reaction of electron-deficient heterocycles with nucleophiles. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/

2017. Large-scale cobalt-catalyzed cross-couplings. Synthesis, 49(19).
DOI: 10.1055/s-0036-1588986