Chemical Identity and Physical Properties

(1S,2R)-(-)-cis-1-Amino-2-indanol (CAS 136030-00-7) is a bicyclic amino alcohol featuring an indane (2,3-dihydro-1H-indene) core with a primary amino group at C-1 and a hydroxyl group at C-2 in a cis relative configuration. The rigid indane framework enforces a well-defined spatial relationship between the two polar functional groups, making the molecule particularly valuable as a chiral scaffold.

Key physical and chemical parameters include a molecular formula of C₉H₁₁NO and a molecular weight of approximately 149.19 g/mol. The compound is typically obtained as a white to off-white crystalline solid. It is soluble in common polar organic solvents such as methanol, ethanol, and dichloromethane, and exhibits limited solubility in nonpolar solvents. The compound is levorotatory, with a negative optical rotation ([α]_D) consistent with its (1S,2R) absolute configuration. Researchers should consult the specific lot certificate of analysis supplied by Aladdin Scientific for precise melting point, optical rotation, and purity data.

Role as a Chiral Auxiliary and Ligand in Asymmetric Synthesis

The combination of a primary amine and a secondary alcohol on a conformationally restricted indane ring positions (1S,2R)-(-)-cis-1-amino-2-indanol as a powerful chiral auxiliary and ligand in asymmetric catalysis. The two heteroatom donors can chelate metal centers or hydrogen-bond to substrates, transmitting chirality efficiently to prochiral reaction partners.

Representative applications include:

• Chiral oxazaborolidine catalysts: Condensation of the amino alcohol with boronic acid derivatives generates chiral oxazaborolidines (CBS-type catalysts), which are employed in the asymmetric borane reduction of prochiral ketones to yield enantioenriched secondary alcohols.
• Chiral ligand design: The compound serves as a starting material for bidentate N,O-ligands used in transition-metal-catalyzed asymmetric reactions, including asymmetric hydrogenation and cyclopropanation.
• Diastereoselective alkylation auxiliaries: Amide or sulfonamide derivatives of the amino group can direct enantioselective transformations at adjacent carbon centers.

The rigid cis-fused ring system provides excellent facial selectivity, which is a key advantage over more flexible acyclic amino alcohol auxiliaries.

Applications in Pharmaceutical and Medicinal Chemistry

(1S,2R)-(-)-cis-1-Amino-2-indanol gained prominence as a key chiral building block in the synthesis of HIV protease inhibitors. Most notably, it is a structural component in the preparation of Indinavir (Crixivan®), an antiretroviral drug developed for the treatment of HIV/AIDS. In this context, the amino alcohol moiety contributes to the pharmacophore of the inhibitor and its stereochemistry is critical for potency and selectivity against the HIV-1 protease active site.

Beyond antiviral applications, the compound serves as a versatile enantiopure synthon for medicinal chemistry programs targeting a range of biological activities. Its well-defined stereochemistry, commercial availability in high enantiomeric excess, and the synthetic handles offered by the amine and hydroxyl groups make it an attractive starting point for structure–activity relationship (SAR) studies. Researchers in medicinal chemistry commonly incorporate indanol amino alcohol-derived substructures into libraries of drug candidates.

Handling, Storage, and Safety Considerations

As with all fine chemicals and research reagents, appropriate laboratory safety practices should be followed when handling (1S,2R)-(-)-cis-1-Amino-2-indanol. The compound contains a primary amine and may be irritating to skin, eyes, and the respiratory tract. Personnel should wear appropriate personal protective equipment (PPE) including gloves, safety glasses, and lab coat. Work in a well-ventilated area or fume hood is recommended.

For storage, the compound should be kept in a tightly sealed container away from moisture, heat, and incompatible materials such as strong acids, strong oxidizers, and reactive acylating agents. Storage at room temperature or under refrigeration (2–8 °C) in a dry environment is generally appropriate, though researchers should refer to the Aladdin Scientific product label and Safety Data Sheet (SDS) for lot-specific recommendations.

To preserve enantiopurity and chemical integrity over time, minimize exposure to atmospheric moisture and light. Always consult the current SDS provided with the product before use.

Ordering and Availability from Aladdin Scientific

(1S,2R)-(-)-cis-1-Amino-2-indanol is available from Aladdin Scientific under SKU A117276. Aladdin Scientific supplies this enantiopure reagent to research laboratories, pharmaceutical companies, and academic institutions worldwide. The product is offered with a certificate of analysis (CoA) detailing purity, optical rotation, and other quality parameters for each lot.

For bulk quantities, custom packaging, or specific purity requirements, researchers and procurement professionals are encouraged to contact Aladdin Scientific's technical sales team. Aladdin Scientific is committed to providing consistent quality and reliable supply of chiral building blocks to support demanding synthetic and medicinal chemistry programs.