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440841

Sigma-Aldrich

(1R,2S)-(+)-cis-1-Amino-2-indanol

99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H11NO
CAS Number:
136030-00-7
Molecular Weight:
149.19
Beilstein/REAXYS Number:
2803743
MDL number:
MFCD00216656
UNSPSC Code:
12352116
PubChem Substance ID:
24867628
NACRES:
NA.22

assay

99%

form

solid

optical activity

[α]22/D +63°, c = 0.2 in chloroform

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+/m0/s1

InChI key

LOPKSXMQWBYUOI-DTWKUNHWSA-N

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Application

This cis-aminoindanol and its antipode have been used in the preparation of a series of potent HIV-1 protease inhibitory peptides. Also, they have served as chiral ligands in the catalytic asymmetric reduction of prochiral ketones with boranes.

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
BCCF2856
BCBZ5228
BCBS1995V
BCBJ4621V
WXBB6699V

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Askin, D. et al.
The Journal of Organic Chemistry, 57, 2771-2771 (1992)
D'Aniello, F. et al.
The Journal of Organic Chemistry, 59, 3762-3762 (1994)
Dorsey, B.D. et al.
Tetrahedron Letters, 34, 1851-1851 (1993)
Thompson, W.J. et al.
Tetrahedron Letters, 33, 2957-2957 (1992)
W J Thompson et al.
Journal of medicinal chemistry, 35(10), 1685-1701 (1992-05-15)
By tethering of a polar hydrophilic group to the P1 or P1' substituent of a Phe-based hydroxyethylene isostere, the antiviral potency of a series of HIV protease inhibitors was improved. The optimum enhancement of anti-HIV activity was observed with the
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Chromatograms

application for HPLC

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