2,4-Dichloro-5-fluoropyrimidine[2]

Updated: 2026-09-18

Overview

2,4-Dichloro-5-fluoropyrimidine (CAS 131860-97-4) is a fluorinated pyrimidine compound primarily employed as a building block in medicinal chemistry. Its molecular structure features reactive chlorine and fluorine atoms at the 2,4 and 5 positions, respectively, enabling selective functionalization for drug development. As a versatile intermediate, it is particularly valuable in synthesizing nucleoside analogs and kinase inhibitors. The compound's commercial significance stems from its role in producing active pharmaceutical ingredients (APIs) for antiviral and oncology treatments, with demand driven by pharmaceutical R&D pipelines.

Physical and Chemical Properties

This crystalline solid exhibits moderate thermal stability with a melting point range of 60-65°C. Its low polarity results in good solubility in dichloromethane, tetrahydrofuran, and other aprotic solvents, while being sparingly soluble in water. The electron-withdrawing effects of chlorine and fluorine atoms enhance its reactivity in nucleophilic aromatic substitution (SNAr) reactions. This property is exploited in stepwise derivatization processes, where the 4-chloro position typically reacts first due to steric and electronic factors. Handling requires caution as it may decompose under prolonged exposure to moisture or heat.

Main Applications

In pharmaceutical manufacturing, 2,4-dichloro-5-fluoropyrimidine serves as a critical precursor for fluoropyrimidine-based drugs. It is extensively used to synthesize prodrugs like capecitabine metabolites and fluorouracil derivatives, which are cornerstone chemotherapeutic agents. Beyond oncology, the compound facilitates development of antiviral medications targeting viral polymerases. Recent applications include kinase inhibitor scaffolds for autoimmune disease treatments. Emerging research explores its utility in PET tracer synthesis and agrochemicals, though pharmaceutical applications dominate current industrial usage.

Safety and Storage

As a halogenated compound, this material requires strict safety protocols. It is classified as corrosive (Skin Corr. 1B) and causes severe skin burns/eye damage. Proper handling mandates nitrile gloves, chemical goggles, and Type 4 protective suits in ventilated enclosures. Storage recommendations include amber glass containers under nitrogen atmosphere at 2-8°C, with desiccants to prevent hydrolysis. Incompatible with strong oxidizers and bases. Spills should be neutralized with inert absorbents followed by professional disposal. SDS documentation must accompany all shipments per GHS regulations.

B2B Procurement Guide

Pharmaceutical-grade material typically commands 98-99% purity (HPLC), with stringent limits on related substances. Buyers should request COAs with detailed impurity profiles, residual solvent data, and chiral purity specifications when applicable. Reliable suppliers provide cGMP-compliant batches with full traceability and ICH stability data. For pilot-scale orders (1-10kg), lead times average 4-6 weeks. Bulk procurement (100kg+) may qualify for 15-25% discounts. Key evaluation criteria include supplier DMF filings, regulatory support documentation, and qualification of polymorphic forms for API integration.