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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:
4292559
MDL number:
MFCD00216655
UNSPSC Code:
12352116
PubChem Substance ID:
24867627
NACRES:
NA.22

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

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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

440833-VAR:
440833-BULK:
440833-1G:
440833-5G:
440833-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG2565
MKBV5584V
MKBQ8102V
01109BD
07612AD

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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
Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2, 4, 6-trimethylphenylsulfinamide.
Davis FA, et al.
The Journal of Organic Chemistry, 68(18), 6894-6898 (2003)
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)
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)
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)
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Chromatograms

application for HPLC

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