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Description
TCI D4122 2,4-Dichloro-5-iodopyrimidine is a heterocyclic synthesis raw material that carries three halogen substituents at different positions on the pyrimidine ring: chlorine at positions 2 and 4, and iodine at position 5. The pyrimidine ring itself is one of the most important scaffolds in medicinal chemistry, since it is present in nucleic acid bases and in a very large number of marketed drugs. In the laboratory, this compound serves as a core framework that can be built up step by step into complex molecules, particularly for the development of kinase inhibitors and antiviral compounds.
The principal value of this compound lies in the orthogonal reactivity of its three halogens, a property highly prized by synthetic chemists. The chlorine at position 4 is generally the most reactive toward nucleophilic aromatic substitution and can be displaced by amines first under mild temperatures, followed by the chlorine at position 2 under more forcing conditions. Meanwhile, the carbon–iodine bond at position 5 is an ideal partner for palladium-catalysed cross-coupling reactions such as Suzuki, Sonogashira, and Heck, because iodine is the best leaving group in the oxidative addition step. This controllable reaction sequence allows chemists to introduce three different substituents onto a single ring in a planned order.
In Indonesian laboratories, this building block is typically used by university research groups, medicinal chemistry laboratories, and pharmaceutical research and development units that construct substituted pyrimidine libraries. It suits work where a single starting scaffold must be diversified into several analogues for structure–activity studies. Because the material is supplied by TCI as a catalogue building block, it fits routine bench-scale synthesis, method development, and small-scale exploratory chemistry rather than production-scale processes.
Laboratory Applications
- Kinase inhibitor development: the pyrimidine core is a recurring motif in kinase-targeting molecules, and the three differentiated halogens allow the required substituent pattern to be assembled in a planned sequence.
- Antiviral compound synthesis: the pyrimidine ring relates directly to nucleic acid bases, making this scaffold a practical entry point for building nucleobase-like analogues in antiviral research programmes.
- Selective nucleophilic aromatic substitution: the position-4 chlorine reacts first with amines under mild temperatures, so chemists can install one amine cleanly before addressing the position-2 chlorine.
- Palladium-catalysed cross-coupling: the carbon–iodine bond at position 5 undergoes Suzuki, Sonogashira, and Heck couplings efficiently because iodine is the best leaving group for oxidative addition.
- Analogue library construction: a single scaffold can be diversified into many derivatives by varying the three substitution steps, supporting structure–activity relationship studies from one common intermediate.
Specifications
- Brand: TCI
- CAS number: 13544-44-0
- Chemical name: 2,4-Dichloro-5-iodopyrimidine
- Product code: D4122
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes: available in TCI catalogue pack sizes; please confirm the required size when ordering
- Storage: store as indicated on the manufacturer's label and accompanying documentation
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from heat, direct sunlight, moisture, and incompatible materials, following the storage conditions stated on the manufacturer's label. Keep the compound in its original supplier container, or in a clean, tightly sealed amber glass container if transferred, and label it clearly. Handle only in a fume hood using appropriate personal protective equipment, including safety goggles, chemical-resistant gloves, and a laboratory coat. Avoid inhalation of dust and any contact with skin and eyes. Halogenated heterocycles should be weighed carefully to minimise dust generation, and containers should be returned to storage promptly after use. Consult the manufacturer's Safety Data Sheet before handling, and dispose of residues and contaminated materials as halogenated chemical waste according to applicable laboratory waste procedures.
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