Tert-Butyl 3-Bromophenethylcarbamate: Handling & Usage Guide

Tert-Butyl 3-Bromophenethylcarbamate is a Boc-protected amine building block featuring a meta-bromophenethyl scaffold, widely employed as a versatile intermediate in palladium-catalyzed cross-coupling reactions and pharmaceutical synthesis workflows.

Product Name

Tert-Butyl 3-Bromophenethylcarbamate

SKU

T729179

Functional Groups

Aryl bromide, Boc-protected amine (carbamate)

Primary Application

Synthetic intermediate for cross-coupling and medicinal chemistry

Protecting Group

tert-Butoxycarbonyl (Boc)

Recommended Storage

Cool, dry, well-ventilated area; away from moisture and light

Chemical Identity and Structure

Tert-Butyl 3-Bromophenethylcarbamate consists of a 3-bromophenethylamine core in which the primary amine is protected as a tert-butyl carbamate (Boc) group. The molecule therefore presents two orthogonal reactive handles: (1) the aryl C–Br bond, amenable to palladium- or nickel-catalyzed cross-coupling transformations such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings; and (2) the Boc-protected amine, which can be cleanly deprotected under mild acidic conditions (e.g., TFA in DCM, or 4 M HCl in dioxane) to reveal the free primary amine for subsequent functionalization.

The meta-substitution pattern of the bromine on the phenyl ring distinguishes this compound from its ortho- and para-isomers and can influence the electronic and steric environment in downstream coupling products, making it a useful tool for structure–activity relationship (SAR) studies in medicinal chemistry programs.

Handling and Safety Guidelines

When working with Tert-Butyl 3-Bromophenethylcarbamate, observe standard laboratory safety precautions for organic reagents containing an aryl bromide moiety:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves, laboratory coat, and safety glasses or goggles at all times during handling.
• Ventilation: Perform weighing and solution preparation in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.
• Skin and Eye Contact: Avoid direct contact. In case of skin contact, wash thoroughly with soap and water. For eye contact, irrigate immediately with copious water and seek medical attention.
• Waste Disposal: Dispose of all waste, including contaminated solvents and solids, in accordance with local, institutional, and governmental regulations for halogenated organic waste.

Always consult the current Safety Data Sheet (SDS) supplied by Aladdin Scientific before use. Specific hazard classifications and first-aid measures are detailed therein.

Storage and Stability

To maintain the integrity and purity of Tert-Butyl 3-Bromophenethylcarbamate over its shelf life, the following storage practices are recommended:

• Temperature: Store at room temperature or under cool conditions (2–8 °C if long-term stability is required). Avoid prolonged exposure to elevated temperatures.
• Moisture: Keep the container tightly sealed and protected from atmospheric moisture, as carbamate functionality can be susceptible to hydrolysis under prolonged wet conditions.
• Light: Store away from direct light to prevent potential photodegradation of the aryl bromide moiety.
• Container integrity: Upon receipt, inspect the container for damage and verify the lot certificate of analysis (CoA) to confirm purity meets specification before use.

If the compound has been stored properly and signs of discoloration or decomposition are observed, perform analytical verification (e.g., TLC, NMR, or HPLC) before committing the material to a critical synthesis step.

Typical Applications in Synthesis

Tert-Butyl 3-Bromophenethylcarbamate serves as a multifunctional building block in several synthetic contexts:

1. Palladium-catalyzed cross-coupling: The aryl bromide is a reliable electrophilic partner in Suzuki–Miyaura (with aryl/vinyl boronic acids), Negishi (organozinc), Sonogashira (terminal alkynes), and Buchwald–Hartwig (amine) couplings. Standard Pd(0) or Pd(II) precatalysts (e.g., Pd(PPh₃)₄, Pd₂(dba)₃, or XPhos Pd G3) are commonly employed.
2. Boc deprotection and downstream amide/sulfonamide formation: Treatment with TFA (20–50% v/v in DCM) or HCl (4 M in dioxane) liberates the free amine, enabling acylation, sulfonylation, reductive amination, or urea formation in fragment-based drug discovery campaigns.
3. Medicinal chemistry and SAR exploration: The meta-bromophenethylamine scaffold appears in various pharmacophores; this Boc-protected derivative allows parallel synthesis of focused libraries targeting receptors or enzymes of interest.
4. Halogen–metal exchange: The aryl bromide can undergo lithiation (n-BuLi, −78 °C) for subsequent reaction with electrophiles, providing access to meta-substituted phenethylamine derivatives not easily accessible via direct synthesis.

Quality and Ordering Information

Tert-Butyl 3-Bromophenethylcarbamate is available from Aladdin Scientific under SKU T729179. Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity and identity data. Researchers are encouraged to:

• Request the CoA and SDS at the time of ordering or download them directly from the Aladdin Scientific product page.
• Confirm that the purity level stated on the CoA meets the requirements of the intended application prior to use.
• Contact Aladdin Scientific technical support for bulk quantities, custom packaging, or questions regarding specific analytical data.

For questions about reagent specifications, grades, and purity standards applicable to this compound, refer to the 试剂的规格、级别和纯度 resources available through Aladdin Scientific customer support channels.

Frequently asked questions

How should I deprotect the Boc group in Tert-Butyl 3-Bromophenethylcarbamate?

The Boc group is routinely removed under acidic conditions: treatment with 20–50% trifluoroacetic acid (TFA) in dichloromethane (DCM) at room temperature for 30–60 minutes, or with 4 M HCl in dioxane, typically affords the free amine in high yield. The resulting amine salt should be neutralized prior to further reactions if needed.

Which cross-coupling reactions are compatible with the aryl bromide in this compound?

The aryl bromide in Tert-Butyl 3-Bromophenethylcarbamate is compatible with a range of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (boronic acids/esters), Negishi (organozinc), Sonogashira (terminal alkynes), and Buchwald–Hartwig amination. Standard Pd(0) or Pd(II) precatalysts and appropriate ligands should be selected based on the coupling partner and desired transformation.

What are the recommended storage conditions to ensure long-term stability?

Store Tert-Butyl 3-Bromophenethylcarbamate in a tightly sealed container in a cool, dry, and well-ventilated area away from direct light and moisture. For extended storage periods, refrigeration at 2–8 °C is advisable. Verify compound integrity by analytical methods (TLC, NMR, or HPLC) if any discoloration or physical change is observed before use.

Is Tert-Butyl 3-Bromophenethylcarbamate suitable for use in medicinal chemistry library synthesis?

Yes, its dual reactive handles — the aryl bromide for cross-coupling and the Boc-protected amine for subsequent functionalization — make it well suited for parallel and combinatorial synthesis of focused compound libraries. The meta-bromo substitution provides a differentiated regiochemical profile relative to ortho- and para-isomers, supporting systematic SAR exploration.

References

1. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
2. Hartwig, J. F. Palladium-catalyzed amination of aryl halides and related reactions. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002.
3. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, NJ, 2007.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.