2-Chloropyrimidine
[CAS# 1722-12-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Chloropyrimidine
• Name: 2-Chloropyrimidine
• Molecular Formula: C₄H₃ClN₂
• Molecular Weight: 114.53
• CAS Registry Number: 1722-12-9
• EC Number: 217-020-2
• SMILES: C1=CN=C(N=C1)Cl

Properties

• Melting point: 66 ºC
• Boiling point: 75-76 ºC (10 mmHg)
• Flash point: 98 ºC

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H315-H317-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

2-Chloropyrimidine is an important chemical compound with a wide range of applications in both industrial and pharmaceutical chemistry. This compound, characterized by a chlorine atom substituted at the 2-position of the pyrimidine ring, is a valuable building block in the synthesis of various chemical entities.

The discovery of 2-chloropyrimidine dates back to the early 20th century when pyrimidine derivatives were first explored for their potential in medicinal chemistry and organic synthesis. Pyrimidine itself is a six-membered aromatic ring containing two nitrogen atoms at positions 1 and 3, and its derivatives have been found to exhibit diverse biological activities. The introduction of a chlorine atom at position 2 further modifies the electronic and steric properties of the pyrimidine ring, enhancing its utility in chemical synthesis.

2-Chloropyrimidine is used extensively as an intermediate in the synthesis of pharmaceuticals. Its reactivity allows it to participate in various chemical reactions, making it a key component in the preparation of more complex molecules. For example, 2-chloropyrimidine can be employed in nucleophilic substitution reactions, where the chlorine atom is replaced by various nucleophiles to form a range of substituted pyrimidine derivatives. These derivatives are then used in the development of drugs with specific therapeutic properties.

In the pharmaceutical industry, 2-chloropyrimidine serves as a precursor for the synthesis of antiviral, anticancer, and anti-inflammatory agents. The compound is involved in the synthesis of drugs such as zidovudine, an antiretroviral medication used in the treatment of HIV, and other important therapeutics. The ability to modify the pyrimidine ring through substitution reactions allows chemists to create compounds with targeted biological activities.

Additionally, 2-chloropyrimidine is used in the synthesis of agrochemicals. It acts as a building block in the preparation of herbicides and pesticides, where its reactivity contributes to the formation of active agricultural chemicals. The versatility of 2-chloropyrimidine in these applications is due to its ability to form various derivatives that exhibit specific biological activities against pests and weeds.

The compound is also employed in materials science, where it is used to synthesize functional materials such as polymers and dyes. The presence of the chlorine atom in 2-chloropyrimidine enhances the material’s properties, such as its stability and solubility, which are crucial for the development of high-performance materials.

Overall, 2-chloropyrimidine is a versatile and valuable chemical intermediate with significant applications in drug discovery, agricultural chemistry, and materials science. Its role as a key building block in the synthesis of a variety of compounds underscores its importance in both industrial and research settings.

References

2021. Palladium-catalyzed Hiyama cross-couplings of 2-chloro pyrimidines with organosilanes. Chemical Papers, 76(3).
DOI: 10.1007/s11696-021-02044-5

2023. Synthesis of azinyl azolyl pyrimidines as new hybrid N,N,N-tridentate ligands for coordination chemistry. Chemistry of Heterocyclic Compounds, 59(9).
DOI: 10.1007/s10593-023-03253-4

2019. Synthesis of 2-(pyrrolidin-1-yl)pyrimidines by reactions of N-(4,4-diethoxybutyl)pyrimidin-2-amine with (hetero)aromatic C-nucleophiles. Chemistry of Heterocyclic Compounds, 55(6).
DOI: 10.1007/s10593-019-02489-3.