440833

(1S,2R)-(−)-cis-1-Amino-2-indanol

99%

• Synonym(s): (1S,2R)-(−)-cis-1-Amino-2-hydroxyindane
• Empirical Formula (Hill Notation): C₉H₁₁NO
• CAS Number: 126456-43-7
• Molecular Weight: 149.19
• Beilstein/REAXYS Number: 4292559
• MDL number: MFCD00216655
• UNSPSC Code: 12352116
• PubChem Substance ID: 24867627
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 99%
• form: powder
• optical purity: ee: 99% (GLC)
• mp: 118-121 °C (lit.)
• functional group: hydroxyl
• SMILES string: N[C@@H]1[C@H](O)Cc2ccccc12
• InChI: 1S/C9H11NO/c10-9-7-4-2-1-3-6(7)5-8(9)11/h1-4,8-9,11H,5,10H2/t8-,9+/m1/s1
• InChI key: LOPKSXMQWBYUOI-BDAKNGLRSA-N

Description

General description

(1S,2R)-(-)-cis-1-Amino-2-indanol is a main constituent of indinavir, a potent HIV (human immunodeficiency virus) protease inhibitor.[1]

Application

1S,2R)-(-)-cis-1-Amino-2-indanol may be used to prepare:

• (-)-1,2,5,6-Tetrahydropyridine by reacting with methyl (E,E)-4-oxo-2-[(2,6,6-trimethylcyclohex-1-enyl)vinyl}but-2-enoate.[2]
• Oxazaborolidine catalysts, which can catalyze the asymmetric reduction of aromatic ketones with high enantioselectivity.[3]
• (R_S,1S,2R)-(-)-2,4,6-Trimethylbenzenesulfinic acid 1-(2,4,6-trimethylbenzenesulfonylamino)indan-2-yl ester.[4]

Used to prepare a mannitol-based scaffold in the study of Plasmepsin II inhibition. Aspartic proteases such as plasmepsins I and II are of interest as targets for new, potential anti-malarials.[5]

Physical properties

Useful chiral ligand for asymmetric synthesis.[6]

Legal Information

Sold under license from Sterling Pharma Solutions Limited.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves