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440833

Sigma-Aldrich

(1S,2R)-(−)-cis-1-Amino-2-indanol

99%

Synonym(s):

(1S,2R)-(−)-cis-1-Amino-2-hydroxyindane

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About This Item

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

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

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General description

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

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.
  • Oxazaborolidine catalysts, which can catalyze the asymmetric reduction of aromatic ketones with high enantioselectivity.
  • (RS,1S,2R)-(-)-2,4,6-Trimethylbenzenesulfinic acid 1-(2,4,6-trimethylbenzenesulfonylamino)indan-2-yl ester.
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.

Physical properties

Useful chiral ligand for asymmetric synthesis.

Legal Information

Sold under license from Sterling Pharma Solutions Limited.

pictograms

Exclamation mark
GHS07

signalword

Warning

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7652
MKCG2565
MKBV5584V
MKBQ8102V
01109BD

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Karolina Ersmark et al.
Bioorganic & medicinal chemistry, 11(17), 3723-3733 (2003-08-07)
A series of C(2)-symmetric compounds with a mannitol-based scaffold has been investigated, both theoretically and experimentally, as Plm II inhibitors. Four different stereoisomers with either benzyloxy or allyloxy P1/P1' side chains were studied. Computational ranking of the binding affinities of
Cis-1-amino-2-indanol in asymmetric synthesis. Part I. A practical catalyst system for the enantioselective borane reduction of aromatic ketones.
Hong Y, et al.
Tetrahedron Letters, 35(36), 6631-6634 (1994)
Aldrichimica Acta, 31, 3-3 (1998)
Highly stereoselective asymmetric 6p-azaelectrocyclization utilizing the novel 7-alkyl substituted cis-1-amino-2-indanols: Formal synthesis of 20-epiuleine.
Tanaka K and Katsumura S.
Journal of the American Chemical Society, 124(33), 9660-9661 (2002)
Chemoenzymatic synthesis of (1S, 2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir.
Demir AS, et al.
Journal of Molecular Catalysis. B, Enzymatic, 9(4), 157-161 (2000)
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Chromatograms

application for HPLC

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