(S)-5-Bromo-2,3-dihydro-1H-inden-1-amine: Properties & Uses
(S)-5-Bromo-2,3-dihydro-1H-inden-1-amine: Properties & Uses
(S)-5-Bromo-2,3-dihydro-1H-inden-1-amine is a enantiomerically enriched chiral primary amine building block featuring a brominated indane scaffold, widely valued in asymmetric synthesis and pharmaceutical intermediate chemistry.
- IUPAC Name
- (S)-5-Bromo-2,3-dihydro-1H-inden-1-amine
- Core Scaffold
- Indane (2,3-dihydro-1H-indene)
- Functional Groups
- Primary amine (–NH₂), aryl bromide (C–Br)
- Stereocentre Configuration
- (S)-configuration at C-1 of the indane ring
- Role in Synthesis
- Chiral building block and pharmaceutical intermediate
- Key Reactivity
- Amine coupling, reductive amination, cross-coupling via C–Br bond
- Storage Recommendation
- Store under inert atmosphere, cool and dry conditions
Chemical Structure and Sterochemistry
(S)-5-Bromo-2,3-dihydro-1H-inden-1-amine belongs to the indanamine family of compounds. The indane (2,3-dihydro-1H-indene) core is a bicyclic system comprising a cyclopentane ring fused to a benzene ring. In this compound, a primary amine group (–NH₂) is installed at the C-1 position of the cyclopentane ring, and a bromine atom is substituted at the C-5 position of the aromatic ring.
The (S)-designation refers to the absolute configuration at the single stereocentre located at C-1. Enantiopure or enantiomerically enriched forms of such cyclic amines are of considerable importance in medicinal chemistry, where the two enantiomers of a chiral drug candidate may exhibit substantially different pharmacological profiles. The rigid bicyclic scaffold restricts conformational flexibility, which can be advantageous for achieving selective target binding.
Physicochemical Properties and Handling
(S)-5-Bromo-2,3-dihydro-1H-inden-1-amine contains two chemically distinct reactive sites: the primary amine and the aryl bromide. As a primary amine, the compound is a moderate base and nucleophile, susceptible to oxidation and moisture. The aryl bromide provides a handle for transition-metal-catalysed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings.
Researchers should handle the compound under an inert atmosphere (nitrogen or argon) when performing moisture- or air-sensitive transformations. Storage in a cool, dry environment away from strong oxidising agents and acids is recommended to maintain compound integrity. Standard personal protective equipment including gloves, eye protection, and appropriate laboratory coat should be used when working with this reagent, consistent with general amine and organobromine compound handling practices.
Applications in Synthesis and Medicinal Chemistry
Chiral indanamines are recognised as valuable scaffolds in drug discovery and development. The combination of a primary amine and an aryl bromide on an enantiomerically defined bicyclic framework makes (S)-5-Bromo-2,3-dihydro-1H-inden-1-amine a versatile building block for constructing complex molecules.
Typical synthetic applications include: (1) acylation or sulfonylation of the amine to introduce amide or sulfonamide linkages; (2) reductive amination to access secondary and tertiary amine derivatives; (3) palladium-catalysed cross-coupling at the C–Br position to introduce aryl, heteroaryl, or vinyl groups; and (4) use as a chiral ligand precursor or resolving agent in asymmetric synthesis. These transformations collectively enable the construction of structurally diverse, enantiopure intermediates relevant to CNS, oncology, and other therapeutic areas where cyclic amine pharmacophores are prevalent.
Quality, Purity and Procurement Considerations
For research applications, the enantiomeric excess (ee) and chemical purity of chiral building blocks are critical quality attributes. Researchers should confirm specifications including chemical purity (typically assessed by HPLC or GC), enantiomeric excess (assessed by chiral HPLC), and identity (confirmed by NMR and/or mass spectrometry) before use in enantioselective synthesis.
Aladdin Scientific supplies (S)-5-Bromo-2,3-dihydro-1H-inden-1-amine (SKU: B731644) to support synthetic chemistry and pharmaceutical research workflows. Procurement teams should verify lot-specific certificates of analysis for purity and ee data, and ensure appropriate cold-chain or ambient shipping conditions are specified based on the compound's stability requirements. For bulk quantities or custom specifications, contacting Aladdin's technical support team is recommended.
Frequently asked questions
What is the significance of the (S)-configuration in this indanamine compound?
The (S)-designation specifies the absolute stereochemistry at the C-1 stereocentre of the indane ring. In medicinal chemistry, enantiomers of a chiral compound can exhibit markedly different biological activities, selectivities, and pharmacokinetic profiles; therefore, using the defined (S)-enantiomer ensures reproducibility and relevance in enantioselective research applications.
What types of chemical reactions can be performed using (S)-5-Bromo-2,3-dihydro-1H-inden-1-amine?
This compound offers dual reactivity: the primary amine can undergo acylation, reductive amination, sulfonylation, and condensation reactions, while the aryl bromide enables palladium-catalysed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig amination, and Negishi coupling, making it a versatile bifunctional building block.
How should (S)-5-Bromo-2,3-dihydro-1H-inden-1-amine be stored to maintain stability?
The compound should be stored in a cool, dry location under an inert atmosphere (nitrogen or argon) and away from strong oxidising agents, strong acids, and moisture. Sealing the container after each use and following the storage conditions specified on the product certificate of analysis will help preserve enantiomeric integrity and chemical purity over time.
What purity and enantiomeric excess specifications should I look for when ordering this compound?
Researchers should request a certificate of analysis (CoA) confirming chemical purity (typically ≥95% or higher by HPLC/GC) and enantiomeric excess (ee) determined by chiral HPLC, along with identity confirmation by NMR or mass spectrometry. For critical asymmetric synthesis applications, higher ee values are essential to avoid stereochemical contamination of the final product.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for amine reactivity and cross-coupling chemistry.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. General reference for stereochemistry of cyclic amines and chiral building blocks.
- Nugent, T. C. (Ed.) Chiral Amine Synthesis: Methods, Developments and Applications. Wiley-VCH, 2010. Reference for asymmetric synthesis of chiral amines including indanamine scaffolds.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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