2-Chloro-5-hydroxypyrimidine (CAS 4983-28-2) is a pyrimidine derivative with a chlorine atom at the 2-position and a hydroxyl group at the 5-position. Because these two functional groups react differently, the compound is a very useful bifunctional heterocyclic building block. The pyrimidine scaffold appears in many modern drugs and agrochemicals. In the laboratory, this compound is used to build molecules that need a pyrimidine core with an oxygen substituent at the 5-position and an attachment point at the 2-position, especially in medicinal chemistry research.
The 5-hydroxyl group behaves much like a phenol. It can be alkylated, turned into an ether through the Mitsunobu reaction, or converted into a triflate for cross-coupling. The 2-chlorine sits between the two ring nitrogen atoms, which activates it for nucleophilic aromatic substitution and palladium-catalysed coupling reactions. By choosing the right reaction sequence, researchers can functionalise both positions stepwise and selectively. This makes the compound a practical starting point for building analogue libraries, where many related structures must come from one common intermediate.
In Indonesia, this material is relevant to pharmaceutical and medicinal chemistry research groups at universities and to drug R&D laboratories. These teams design and synthesise new heterocyclic compounds as part of discovery and optimisation programmes. Supplied under the TCI brand, it gives Indonesian synthetic chemists a well-defined pyrimidine intermediate for small-scale exploratory synthesis, structure–activity relationship studies and academic projects. It works especially well where a single core needs to be modified in several directions over the course of a project.
Related TCI products
- Medicinal chemistry scaffold synthesis: the pyrimidine core is common in modern drugs, so this compound gives researchers a direct route to drug-like molecules with oxygen substitution at the 5-position.
- Nucleophilic aromatic substitution (SNAr): the 2-chlorine is activated by the two adjacent ring nitrogens, so amines, alkoxides and thiolates can displace it to add new substituents at the 2-position.
- Palladium-catalysed cross-coupling: the activated 2-chloro position can take part in palladium-catalysed coupling reactions, which lets chemists form new carbon–carbon or carbon–heteroatom bonds on the pyrimidine ring.
- O-functionalisation of the 5-hydroxyl group: the phenol-like hydroxyl can be alkylated, turned into an ether through the Mitsunobu reaction, or converted into a triflate that then serves as a second cross-coupling handle.
- Analogue library construction: because the two positions react differently and can be functionalised stepwise and selectively, one intermediate can produce a series of related compounds for structure–activity relationship studies.
| Brand | TCI (product code C3685) |
|---|---|
| CAS number | 4983-28-2 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | standard TCI pack sizes; please contact AMI Scientific for available options |
| Physical form | see the TCI product specification and certificate of analysis |
| Storage | follow the conditions on the TCI label and Safety Data Sheet (SDS) |
Store 2-Chloro-5-hydroxypyrimidine in its original, tightly closed TCI container, following the storage conditions on the product label and Safety Data Sheet. Keep it in a cool, dry, well-ventilated place away from direct sunlight, moisture and incompatible substances such as strong oxidising agents. Reseal the container promptly after each use to protect the contents from air and humidity. Handle the compound in a fume hood or another well-ventilated area, and wear standard laboratory protective equipment, including safety glasses, chemical-resistant gloves and a lab coat. Avoid creating dust and avoid contact with skin, eyes and clothing. Read the SDS before first use, and dispose of residues and contaminated materials according to institutional and local chemical waste regulations.
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