Description

(5-Bromo-2-chloropyrimidin-4-yl)methanol (CAS No. 1785541-95-8) is a high-purity halogenated pyrimidine derivative with the molecular formula C₅H₄BrClN₂O. This compound is a valuable heterocyclic building block for pharmaceutical and agrochemical research, particularly in the synthesis of nucleoside analogs and kinase inhibitors. The presence of both bromo and chloro substituents on the pyrimidine ring enhances its reactivity in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings. The hydroxymethyl group at the 4-position offers further functionalization potential via esterification or oxidation. Supplied as an off-white to pale yellow crystalline powder with ≥95% purity (HPLC), it is ideal for medicinal chemistry and structure-activity relationship (SAR) studies. Store under inert conditions at 2-8°C to ensure stability.

Properties

• CAS Number: 1785541-95-8
• Complexity: 116
• IUPAC Name: (5-bromo-2-chloro-pyrimidin-4-yl)methanol
• InChI: InChI=1S/C5H4BrClN2O/c6-3-1-8-5(7)9-4(3)2-10/h1,10H,2H2
• InChI Key: WXVPZWWUFMDLML-UHFFFAOYSA-N
• Exact Mass: 221.91955
• Molecular Formula: C5H4BrClN2O
• Molecular Weight: 223.45
• SMILES: C1=C(C(=NC(=N1)Cl)CO)Br
• Topological: 46
• Monoisotopic Mass: 221.91955
• Synonyms: (5-Bromo-2-chloropyrimidin-4-yl)methanol, 1785541-95-8, 102-019-0, 4-Pyrimidinemethanol, 5-bromo-2-chloro-, KWC54195, G88713

Application

This compound serves as a versatile intermediate in drug discovery, particularly for modifying pyrimidine cores in kinase inhibitor development. It is used in the synthesis of antiviral and anticancer agents due to its ability to act as a scaffold for targeted modifications. Researchers also employ it in fragment-based ligand design for probing enzyme active sites. Its halogenated structure makes it suitable for palladium-catalyzed cross-coupling reactions to generate diverse libraries for high-throughput screening.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Dam. 1 (100%)
• STOT SE 3 (100%)

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