(1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol

• ChemBase ID: 78415
• Molecular Formular: C9H11NO
• Molecular Mass: 149.18974
• Monoisotopic Mass: 149.08406398
• SMILES: N[C@@H]1[C@@H](Cc2ccccc12)O
• Canonical SMILES: N[C@@H]1[C@H](O)Cc2c1cccc2
• InChI: 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
• InChIKey: LOPKSXMQWBYUOI-BDAKNGLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol
• IUPAC Traditional name: (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol
• Synonyms: (1S,2R)-(-)-cis-1-Amino-2-hydroxyindane; (1S,2R)-(-)-cis-1-Amino-2-indanol; (1S,2R)-(-)-1-Amino-2,3-dihydro-1H-inden-2-ol; (1S,2R)-(-)-1-Aminoindan-2-ol; (1S,2R)-(-)-1-Amino-2-hydroxyindane; (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol; (1S,2R)-(-)-顺式-1-氨基-2-茚满醇; (1S,2R)-(-)-顺式-1-氨基-2-茚醇; (1S,2R)-(-)-cis-1-氨-2茚醇

Database IDs

• CAS Number: 126456-43-7
• MDL Number: MFCD00216655
• Beilstein Number: 4292559
• PubChem SID: 24867627; 162043182
• PubChem CID: 9866743

CALCULATED PROPERTIES

• Acid pKa: 14.380486
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.3743553
• LogD (pH = 7.4): -1.1841465
• Log P: 0.5683349
• Molar Refractivity: 43.4737 cm^3
• Polarizability: 17.190062 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 117-118°C; 118-121 °C(lit.); 118-121°C; 118-122 °C
• Optical Rotation: [α]20/D -61°, c = 0.5 in chloroform; [α]20/D -64±5°, c = 0.2% in chloroform; -61 (c=0.5 in chloroform)
• Hydrophobicity(logP): 0.348

Safety Information

• Storage Warning: Air Sensitive; Irritant
• RTECS: NK7525500
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN3259
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95%; 97%; 99%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C9H11NO

DETAILS

Sigma Aldrich - 440833

Application
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.2
Packaging
1, 5, 25 g in glass bottle
Legal Information
Sold under license from Shasun Chemicals and Drugs Limited.
Physical properties
Useful chiral ligand for asymmetric synthesis.1

Sigma Aldrich - 08243

Other Notes
Chiral building block for preparing HIV protease inhibitors1; Chiral ligand: oxazaborolidine-cat. asymmetric reduction of ketones2,3