6-Bromo-2,3-dihydro-1H-inden-5-ol: Properties & Applications
6-Bromo-2,3-dihydro-1H-inden-5-ol: Properties & Applications
6-Bromo-2,3-dihydro-1H-inden-5-ol is a halogenated indanol derivative that serves as a versatile building block in organic synthesis, particularly in the preparation of pharmaceutically relevant scaffolds.
- IUPAC Name
- 6-Bromo-2,3-dihydro-1H-inden-5-ol
- SKU
- B728513
- Molecular Formula
- C9H9BrO
- Core Scaffold
- Indane (2,3-dihydro-1H-indene)
- Key Functional Groups
- Phenolic hydroxyl (–OH) and aryl bromide (C–Br)
- Primary Use
- Synthetic intermediate and building block in medicinal chemistry
Chemical Structure and Properties
6-Bromo-2,3-dihydro-1H-inden-5-ol belongs to the indane family of compounds, featuring a partially saturated bicyclic framework in which a cyclopentane ring is fused to a benzene ring. The molecule carries two key functional groups on the aromatic ring: a phenolic hydroxyl group at position 5 and a bromine substituent at position 6. These adjacent substituents confer distinct reactivity patterns and influence the compound's physical properties.
The phenolic –OH group renders the molecule weakly acidic and capable of hydrogen-bond donation and acceptance, which is important for solubility modulation and target engagement in drug design. The aryl bromide at C-6 is an excellent handle for transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Sonogashira, and Buchwald–Hartwig couplings, making this compound a highly valuable synthetic intermediate.
Synthesis and Synthetic Utility
The indane core present in 6-Bromo-2,3-dihydro-1H-inden-5-ol can be accessed through several established routes, including Friedel–Crafts cyclization of appropriate arylpropyl precursors or catalytic hydrogenation of indene derivatives. Selective bromination of the parent 2,3-dihydro-1H-inden-5-ol at the 6-position, guided by the directing effects of the hydroxyl group, is a straightforward approach to introduce the halogen handle.
Once in hand, this building block participates in a broad range of transformations. The C–Br bond undergoes oxidative addition with Pd(0) and Ni(0) catalysts, enabling fragment coupling with aryl-, heteroaryl-, vinyl-, and alkynyl partners. The phenol can be selectively protected as an ether, ester, or carbonate prior to cross-coupling, or converted to a triflate to serve as an additional electrophilic coupling partner. This orthogonal reactivity makes the compound particularly attractive for multi-step synthesis campaigns.
Research and Medicinal Chemistry Applications
The indane scaffold is found in a number of biologically active compounds and approved drugs, underscoring the pharmaceutical relevance of indane-based building blocks. The combination of the lipophilic indane ring system with a phenolic hydroxyl group and an aryl bromide provides a privileged starting point for the exploration of structure–activity relationships (SAR) in drug discovery programs.
6-Bromo-2,3-dihydro-1H-inden-5-ol is particularly useful in programs targeting enzymes and receptors that recognize phenolic or biaryl motifs. It can serve as a precursor to biaryl- or heteroaryl-substituted indanol derivatives, which are commonly explored as kinase inhibitors, protease inhibitors, and GPCR modulators. Researchers in total synthesis may also employ this compound as a key fragment in the construction of natural product analogues bearing an indane or indanol subunit.
Handling, Storage, and Safety Considerations
As with all organobromine compounds bearing a reactive phenol, standard laboratory precautions should be observed when handling 6-Bromo-2,3-dihydro-1H-inden-5-ol. Personal protective equipment including nitrile gloves, safety glasses, and a laboratory coat should be worn at all times. Operations that may generate dust or aerosols should be conducted in a well-ventilated fume hood.
The compound should be stored in a tightly sealed container, away from light, heat, and moisture. A cool, dry environment (typically 2–8 °C or as specified on the product label) is recommended for long-term stability. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use for detailed hazard information, first-aid measures, and disposal guidance.
Frequently asked questions
What makes 6-Bromo-2,3-dihydro-1H-inden-5-ol useful as a synthetic building block?
The compound contains two orthogonally reactive functional groups: a phenolic hydroxyl that can be protected, alkylated, or converted to a triflate, and an aryl bromide that enables a wide range of palladium- and nickel-catalyzed cross-coupling reactions. This dual reactivity allows chemists to elaborate the molecule in multiple directions within a synthetic sequence.
How should I store 6-Bromo-2,3-dihydro-1H-inden-5-ol to maintain its stability?
Store the compound in a tightly sealed container under cool, dry, and dark conditions, typically at 2–8 °C or as indicated on the Aladdin Scientific product label. Protecting the material from moisture and light helps prevent hydrolysis of the aryl bromide and oxidative degradation of the phenol. Always refer to the current SDS for specific storage recommendations.
Which cross-coupling reactions are compatible with the aryl bromide in this compound?
The aryl C–Br bond in 6-Bromo-2,3-dihydro-1H-inden-5-ol is compatible with several well-established palladium-catalyzed cross-coupling protocols, including Suzuki–Miyaura (with boronic acids/esters), Sonogashira (with terminal alkynes), Heck (with alkenes), and Buchwald–Hartwig (with amines) reactions. Nickel-catalyzed variants may also be applicable depending on the reaction conditions employed.
What is the molecular formula and molecular weight of 6-Bromo-2,3-dihydro-1H-inden-5-ol?
The molecular formula of 6-Bromo-2,3-dihydro-1H-inden-5-ol is C9H9BrO. The exact molecular weight can be calculated from atomic masses (C: 12.011, H: 1.008, Br: 79.904, O: 15.999) and is approximately 213.07 g/mol; please verify the precise value against the current Aladdin Scientific certificate of analysis.
References
- March, J.; Smith, M. B. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed.; Wiley: Hoboken, NJ, 2013.
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
- Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
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