5-Bromo-2-(bromomethyl)pyrimidine 1193116-74-3 98% white to off-white crystalline solid pharmaceutical intermediate

1. Product Overview

5-Bromo-2-(bromomethyl)pyrimidine (CAS 1193116-74-3) is a bifunctional brominated pyrimidine derivative featuring a bromine substituent at the 5-position and a reactive bromomethyl group at the 2-position of the pyrimidine ring. Also referred to as Pyrimidine, 5-bromo-2-(bromomethyl)-, it serves as a versatile electrophilic building block in medicinal chemistry and heterocyclic synthesis. The compound typically appears as a white to off-white crystalline solid with a reported melting point of 55–57 °C, widely used for introducing the 5-bromo-2-pyrimidinyl moiety via nucleophilic substitution at the benzylic bromide and cross-coupling at the aryl bromide, making it a key intermediate for constructing pyrimidine-based active pharmaceutical ingredients (APIs) and agrochemicals.

2. Key Features and Advantages

• Bifunctional reactivity: aryl bromide supports Suzuki/Miyaura, Sonogashira cross-couplings; benzylic bromomethyl enables SN2 with amines, thiols, alcohols, and cyanides for library diversification.

• Pyrimidine core is a privileged heterocycle in drug discovery (kinase inhibitors, antivirals, antifolates), supporting rapid SAR exploration.

• High purity grade (≥98%) ensures clean conversion in multi-step pharmaceutical workflows with minimal halogen-related byproducts.

• Well-defined crystalline solid with mp 55–57 °C, facilitating handling, weighing, and QC by melting point and HPLC/NMR.

• Compatible with standard protecting-group and orthogonal synthesis strategies in nucleoside and heterocycle programs.

3. Main Applications

• Pharmaceutical intermediate for pyrimidine-based drug candidates, especially kinase inhibitors, antiviral and anticancer R&D.

• Building block for constructing 2-substituted-5-bromopyrimidines, fused pyrimido[4,5-d]pyrimidines, and purine analogs via sequential cross-coupling then SN2.

• Intermediate in custom synthesis and CRO/CDMO projects targeting novel N-heterocyclic libraries and nucleoside mimetics.

• Used in academic and industrial research for method development in Pd-catalyzed cross-couplings of dibromopyrimidines and benzylic functionalization.

• Precursor to 5-bromo-2-pyrimidinemethanol and derived ethers/amines through SN2 with hydroxide or nitrogen/oxygen nucleophiles.

4. Technical Specifications

5. Storage and Handling

Store in a cool, dry place at 2–8 °C in a tightly sealed, light-protected container under an inert atmosphere (nitrogen or argon) to prevent hydrolysis of the benzylic bromide and minimize darkening. For long-term storage, keep at –20 °C in desiccated conditions. Avoid contact with strong bases, nucleophiles, or moisture which can promote premature substitution or elimination. Handle in a well-ventilated area with standard PPE (lab coat, nitrile gloves, safety glasses). Reseal promptly after use. Under recommended conditions, shelf life is typically 12–24 months; periodic HPLC check advised due to benzylic bromide lability.

6. Safety Overview

Intended for research and synthetic use only; not for direct human or veterinary therapeutic administration. May cause irritation to eyes, skin, and respiratory tract upon contact or dust inhalation (GHS07, H302/H319). Brominated aromatics and alkyl bromides can be irritating and may be absorbed through skin; handle as a reactive halogenated organic intermediate with standard precautions. Prevent dust/vapor generation. In case of skin contact, wash thoroughly with soap and water; for eye contact, rinse cautiously with plenty of water and seek medical advice if irritation persists. Avoid contact with strong bases or metals. Dispose according to local regulations for halogenated organic laboratory chemicals. Always consult the latest SDS from the supplier before use.