What Is tert-Butyl 2-(4-Bromophenyl)propan-2-ylcarbamate?

tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate (SKU T692278) is an organic compound that combines two synthetically important functional groups in a single molecule: a tert-butoxycarbonyl (Boc) protected tertiary amine and a para-substituted aryl bromide. The Boc group is one of the most widely employed nitrogen-protecting groups in synthetic organic and medicinal chemistry, valued for its stability under basic and neutral conditions and its selective removability under mild acidic conditions (e.g., trifluoroacetic acid or HCl in dioxane). The aryl bromide moiety is a well-established electrophilic partner in transition-metal-catalyzed reactions.

The compound features a quaternary carbon center bearing the nitrogen, the bromophenyl ring, and two methyl groups, conferring steric rigidity that can be advantageous when designing conformationally constrained pharmacophores or ligands.

What Are the Key Synthetic Applications?

This compound serves as a dual-handle building block, enabling sequential or orthogonal transformations at either the aryl bromide or the Boc-protected nitrogen:

• Palladium-catalyzed cross-coupling: The aryl bromide is well-suited for Suzuki–Miyaura, Buchwald–Hartwig, Negishi, Stille, and Heck coupling reactions, allowing installation of diverse aryl, vinyl, or amino substituents on the phenyl ring.
• Amine liberation: Removal of the Boc group under acidic conditions (e.g., TFA/DCM or 4 M HCl in dioxane) releases the free tertiary amine, which can then participate in acylation, sulfonylation, reductive amination, or further coupling steps.
• Drug discovery intermediates: The quaternary carbon–nitrogen motif is encountered in CNS-active compounds and kinase inhibitor scaffolds, making this building block relevant to medicinal chemistry programs targeting such structural features.

These attributes make T692278 a flexible intermediate for constructing complex nitrogen-containing frameworks in a convergent synthetic strategy.

How Should This Compound Be Stored and Handled?

Storage: Store tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate in a tightly sealed container in a cool, dry, and well-ventilated area, protected from moisture and direct light. Carbamate compounds can be sensitive to prolonged exposure to humidity, which may promote slow hydrolysis of the Boc group over time.

Handling precautions: As with all fine chemical reagents, handle with appropriate personal protective equipment (PPE) including gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be performed in a fume hood. Consult the Safety Data Sheet (SDS) for detailed hazard information before use.

Waste disposal: Dispose of waste in accordance with local, regional, and national regulations governing organic chemical waste. Do not dispose of down drains or in municipal waste streams.

How to Order T692278 from Aladdin Scientific

tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate is available from Aladdin Scientific under SKU T692278. To place an order:

1. Search for the SKU or full product name on the Aladdin Scientific website.
2. Select the desired quantity and purity grade, then add to your cart.
3. Registered institutional and corporate accounts may access volume pricing and credit terms. Contact our sales team for bulk inquiries.
4. For questions about lead times, availability, certificates of analysis (CoA), or custom packaging, contact Aladdin Scientific customer service directly.

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