5-Bromoindan-1-amine: Properties, Handling & Lab Use Guide

5-bromoindan-1-amine is a halogenated bicyclic primary amine that serves as a versatile building block in medicinal chemistry, enabling diverse C–N bond-forming reactions and further functionalization through its aryl bromide handle.

Chemical Name

5-bromoindan-1-amine

Molecular Formula

C₉H₁₀BrN

Molecular Weight

212.09 g/mol

Functional Groups

Primary aliphatic amine; aryl bromide

Typical Appearance

Colorless to pale yellow liquid or low-melting solid

Key Applications

Medicinal chemistry intermediate; cross-coupling partner; chiral amine scaffold

Storage Conditions

Store under inert atmosphere at 2–8 °C, protected from light and moisture

Aladdin SKU

B678904

Chemical Identity and Physical Properties

5-Bromoindan-1-amine (SKU: B678904) is a bicyclic compound comprising a fused cyclopentane and benzene ring system — the indane scaffold — bearing a primary amine at the 1-position and a bromine substituent at the 5-position of the aromatic ring. Its molecular formula is C₉H₁₀BrN with a molecular weight of approximately 212.09 g/mol.

The compound possesses two complementary reactive sites: (1) a primary aliphatic amine (–NH₂) at the benzylic stereocenter, which is nucleophilic and readily participates in acylation, reductive amination, sulfonamide formation, and urea/carbamate synthesis; and (2) an aryl bromide, which is an excellent electrophilic handle for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig amination, and Negishi coupling.

The chiral center at C-1 means the compound can be obtained and used as a racemate or as enantiopure material, making it valuable for structure–activity relationship (SAR) studies where stereochemical configuration influences biological activity. Researchers should confirm the specific stereochemical form supplied (racemic vs. enantiopure) before use in chiral applications.

Synthetic Applications and Research Uses

5-Bromoindan-1-amine is widely employed as a bifunctional building block in pharmaceutical and agrochemical discovery programs. The dual reactivity of the amine and aryl bromide allows sequential or orthogonal functionalization strategies in multi-step synthesis.

Amide and Sulfonamide Formation: The primary amine reacts smoothly with activated carboxylic acids (acid chlorides, NHS esters, or via EDC/DCC-mediated coupling) and sulfonyl chlorides to afford amides and sulfonamides, respectively. These transformations are typically run in anhydrous dichloromethane or DMF with a suitable base (e.g., triethylamine or DIPEA) at 0 °C to room temperature.

Palladium-Catalyzed Cross-Coupling: The aryl bromide serves as an electrophilic coupling partner. Suzuki–Miyaura coupling with arylboronic acids installs biaryl motifs, while Buchwald–Hartwig amination introduces aryl amine diversity. Standard Pd(0) or Pd(II) precatalysts (e.g., Pd(PPh₃)₄, Pd₂(dba)₃) with appropriate phosphine ligands and base in toluene or dioxane are suitable conditions.

Reductive Amination: The amine can be converted to secondary or tertiary amines via condensation with aldehydes or ketones followed by reduction with NaBH₄, NaBH₃CN, or NaBH(OAc)₃.

Drug Discovery: The indanamine scaffold is present in several bioactive molecules and CNS-targeted drug candidates. 5-Bromoindan-1-amine provides a rigid, conformationally restricted amine surrogate compared to flexible aliphatic amines, which can improve selectivity and metabolic stability in lead optimization.

Safe Handling, Storage and Disposal

Personal Protective Equipment (PPE): Handle 5-bromoindan-1-amine in a well-ventilated fume hood. Wear nitrile gloves, a laboratory coat, and safety glasses. Primary amines can be sensitizers and irritants; avoid skin contact and inhalation of vapors or dust.

Storage: Store the compound under an inert atmosphere (nitrogen or argon) at 2–8 °C, away from light, heat, and moisture. Primary amines are susceptible to oxidation and carbamation by atmospheric CO₂; keep the container tightly sealed and use desiccant where appropriate. Check the supplier's certificate of analysis (CoA) for specific purity and recommended storage conditions.

Stability: The aryl bromide is stable under standard laboratory storage conditions. The free amine form may gradually yellow upon prolonged air exposure; if discoloration occurs, re-check purity by NMR or HPLC before use in sensitive reactions.

Disposal: Dispose of all waste containing this compound in accordance with local, national, and institutional regulations for halogenated organic waste. Do not pour down the drain. Consult your institution's Environmental Health and Safety (EHS) office for approved disposal procedures.

First Aid: In case of skin contact, wash thoroughly with soap and water. For eye contact, rinse with copious water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air immediately.

Quality, Purity and Analytical Verification

Aladdin Scientific supplies 5-bromoindan-1-amine (SKU: B678904) with a certificate of analysis (CoA) specifying purity determined by HPLC or GC. Researchers should request and review the CoA before use to confirm that purity meets the requirements of their intended application.

Identity Verification: The compound can be confirmed by ¹H NMR spectroscopy. Key signals include: aromatic protons of the brominated indane ring (~7.2–7.4 ppm), the methine proton at C-1 bearing the amine (~4.3–4.6 ppm, dd), methylene protons of the cyclopentane ring (~1.8–3.0 ppm), and the amine protons (broad, exchangeable). ¹³C NMR and mass spectrometry (ESI-MS, m/z ≈ 212/214 with the characteristic isotope pattern of one bromine) further confirm identity.

Enantiomeric Purity: For applications requiring specific stereochemistry, enantiomeric excess (ee) should be determined by chiral HPLC or polarimetry. Confirm with Aladdin Scientific or the manufacturer whether the supplied lot is racemic or enantiopure.

Moisture Sensitivity: Karl Fischer titration can be used to determine residual water content if moisture-sensitive downstream reactions are planned.

Ordering Information and Regulatory Compliance

5-Bromoindan-1-amine is available from Aladdin Scientific under SKU B678904. To place an order, visit the Aladdin Scientific website or contact your regional sales representative. Bulk quantities and custom packaging may be available upon request.

Regulatory Status: This compound is intended for research use only (RUO) and is not approved for human therapeutic, diagnostic, or veterinary use. It is not classified as a controlled substance under general schedules; however, researchers should verify the regulatory status in their jurisdiction before procurement, particularly for import/export across international borders.

Documentation: Safety Data Sheets (SDS) and certificates of analysis are available on the Aladdin Scientific product page. For GMP-grade or cGMP-sourced material, please contact Aladdin Scientific to discuss specific requirements.

Returns and Quality Issues: If the product does not meet the stated specifications, contact Aladdin Scientific customer service within the stated returns window. Retain the original packaging and CoA, as these will be required for any return or replacement process.

Frequently asked questions

What is the difference between racemic and enantiopure 5-bromoindan-1-amine, and does it matter for my experiment?

Racemic 5-bromoindan-1-amine contains equal amounts of (R)- and (S)-enantiomers, whereas enantiopure material contains predominantly one enantiomer (typically >95% ee). For achiral synthetic transformations such as amide coupling or Suzuki cross-coupling, the racemate is usually sufficient. However, for biological assays, receptor binding studies, or chiral catalyst development where stereochemistry influences activity or selectivity, enantiopure material is recommended. Always confirm the stereochemical form on the CoA before use.

How should I set up a Suzuki–Miyaura coupling using 5-bromoindan-1-amine as the aryl bromide partner?

A typical procedure uses Pd(PPh₃)₄ (2–5 mol%) or a Pd-PEPPSI complex as catalyst, an arylboronic acid (1.2–1.5 equiv), and K₂CO₃ or Cs₂CO₃ (2–3 equiv) as base in a mixture of dioxane/water (4:1) at 80–100 °C under nitrogen. The free amine does not typically interfere but may coordinate to palladium; if low yields are observed, protect the amine as its Boc carbamate prior to coupling and deprotect afterward. Monitor reaction progress by TLC or LC-MS.

What are the signs that my 5-bromoindan-1-amine has degraded, and can I still use it?

Signs of degradation include visible yellowing or browning of the sample, a change in odor, and the appearance of new peaks by HPLC or NMR compared to the original CoA. Primary amines can absorb CO₂ to form carbamic acid/carbamate species, and oxidation products may also form. If purity by HPLC drops below your application's threshold (typically <95% for medicinal chemistry), re-purification by column chromatography or recrystallization is recommended before use. Do not use visibly degraded material in quantitative biological assays without re-assaying purity.

Can 5-bromoindan-1-amine be used directly in reductive amination reactions?

Yes. The primary amine of 5-bromoindan-1-amine condenses with aldehydes or ketones to form an imine or iminium intermediate, which is then reduced to give a secondary or tertiary amine. NaBH(OAc)₃ in DCE or MeOH at room temperature is a mild and selective reductant suitable for most substrates. Avoid strongly acidic conditions that could also promote reduction of the aryl bromide if sensitive metal catalysts are present. Confirm product identity by MS and NMR.

References

1. Pharmablock Sciences (Nanjing), Inc. Product page: PBLJD0264, 5-bromoindan-1-amine. Retrieved from Pharmablock website.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for amine reactivity and cross-coupling reactions.)
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
4. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Rational Development of Practical Catalysts for Aromatic Carbon–Nitrogen Bond Formation. Acc. Chem. Res. 1998, 31, 805–818. doi:10.1021/ar9600650

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