440841
(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:
Molecular Weight:
149.19
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2803743
Assay:
99%
Form:
solid
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
SMILES string
N[C@H]1[C@@H](O)Cc2ccccc12
InChI key
LOPKSXMQWBYUOI-DTWKUNHWSA-N
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
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Thompson, W.J. et al.
Tetrahedron Letters, 33, 2957-2957 (1992)
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)
S D Young et al.
Journal of medicinal chemistry, 35(10), 1702-1709 (1992-05-15)
A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides
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