2,4-Dichloropyrimidine [CAS No. 3934-20-1]

Empirical Formula (Hill Notation): C₄H₂Cl₂N₂

CAS Number: 3934-20-1

Molecular Weight: 148.98

Product ID: VV-002 Category: Pharmaceutical Intermediates

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Description

Description

General description

2,4-Dichloropyrimidine is a human skin sensitizer. It undergoes effective one-pot, regioselective double Suzuki coupling reaction to yield diarylated pyrimidines.

2,4-Dichloropyrimidine was used in the synthesis of medicinally important 4-aryl-5-pyrimidinylimidazole.

2,4-Dichloropyrimidine, also known as 2,4-DCP or simply dichloropyrimidine, is a heterocyclic organic compound with the chemical formula C4H2Cl2N2. It is a white to off-white crystalline powder that is soluble in organic solvents but insoluble in water. The compound belongs to the class of halogenated pyrimidines, which are widely used as intermediates in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.

Properties and Preparation

2,4-Dichloropyrimidine has a molecular weight of 148.98 g/mol and a melting point of 42-45 °C. Its boiling point is 237-238 °C at 760 mmHg, and its density is 1.44 g/cm3. The compound is stable under normal conditions but can decompose upon heating or exposure to light. It is a strong irritant to eyes and skin and can cause respiratory and digestive problems if ingested or inhaled.

2,4-Dichloropyrimidine can be prepared by various methods, such as chlorination of pyrimidine with sulfuryl chloride or phosphorus pentachloride, or direct chlorination of 2,4-dihydroxypyrimidine with thionyl chloride or phosphorus oxychloride. The yield and purity of the product depend on the reaction conditions, such as temperature, time, and stoichiometry, as well as the quality of the starting materials and the purification methods.

Application

2,4-Dichloropyrimidine is a versatile building block in the synthesis of various biologically active compounds, such as antiviral agents, fungicides, herbicides, and insecticides. It can be used as a precursor for the preparation of pyrimidine-based drugs, such as zaleplon, a hypnotic agent for the treatment of insomnia, and ralitoline, a nootropic agent for the enhancement of memory and cognition. It can also be used as a starting material for the synthesis of pyrimidine nucleosides and nucleotides, which are important components of DNA and RNA.

2,4-Dichloropyrimidine is also used as an intermediate in the manufacture of agrochemicals, such as chlorfenapyr, a broad-spectrum insecticide and acaricide, and flucarbazone, a herbicide for the control of grassy weeds in crops. It can also be used as a reagent in organic synthesis, such as the conversion of aldehydes and ketones to the corresponding pyrimidines, or the preparation of pyrimidine-2,4,6-triones by reaction with urea.