What Is 2-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazole?

2-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazole (SKU B732538) is a halogenated, N-protected imidazole derivative. The imidazole nitrogen at the N1 position bears a tetrahydropyranyl (THP) protecting group, which is introduced to prevent unwanted N–H reactivity and to improve solubility and stability during downstream synthetic operations.

The C-2 bromine atom serves as the primary reactive site, enabling the compound to participate in palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Negishi), copper-mediated coupling, or halogen–metal exchange (lithiation) to generate 2-imidazolyl organometallic intermediates.

This compound is commercially available from Aladdin Scientific (SKU B732538) and is intended for use as a synthetic building block in research-scale chemistry.

Physical and Chemical Properties

The compound has the molecular formula C₈H₁₁BrN₂O and a molecular weight of approximately 231.09 g/mol. It contains an aromatic imidazole ring fused with the reactivity imparted by the C-2 bromo substituent, and a non-aromatic THP ring at N1.

As a crystalline or low-melting solid (exact melting point should be confirmed from the Certificate of Analysis), it is expected to be soluble in common organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate, and dimethylformamide. Aqueous solubility is limited due to the lipophilic THP group.

The THP protecting group is acid-labile and can be removed under mildly acidic conditions (e.g., dilute HCl, p-TsOH, or acidic ion-exchange resin), regenerating the free N–H imidazole after the synthetic sequence is complete.

Synthetic Applications and Handling

Cross-coupling reactions: The C-2 bromine makes this compound a suitable electrophilic partner in transition-metal-catalyzed reactions. Palladium-catalyzed Suzuki–Miyaura coupling with aryl or heteroaryl boronic acids, and Negishi coupling with organozinc reagents, are well-established strategies for introducing carbon substituents at the C-2 position of the imidazole core.

Halogen–metal exchange: Treatment with n-BuLi or t-BuLi at low temperature (typically –78 °C) in anhydrous THF affords the 2-lithio-1-(THP)-imidazole intermediate, which can be quenched with various electrophiles (aldehydes, ketones, chlorosilanes, etc.).

Handling precautions: The compound should be handled under inert atmosphere (nitrogen or argon) to prevent moisture-induced hydrolysis of the THP protecting group. Standard laboratory PPE (gloves, safety glasses, lab coat) is required. As an organobromine compound, it should be treated as a potential irritant; consult the Safety Data Sheet (SDS) before use.

Storage: Store in a tightly sealed container in a cool, dry place away from light and moisture. Refrigeration (2–8 °C) is typically recommended to maximize shelf life. Confirm specific storage conditions on the product label and CoA.

Ordering and Quality Information

2-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazole is available from Aladdin Scientific under SKU B732538. Researchers should reference this SKU when placing orders to ensure correct product identification.

Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity (typically determined by GC, HPLC, or NMR), appearance, and physical constants. Customers are encouraged to review the CoA upon receipt to confirm product quality meets the requirements of their application.

For bulk quantities, custom synthesis inquiries, or technical support, contact Aladdin Scientific's customer service team directly through the official website or regional distributors.