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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:
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.)

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Askin, D. et al.
The Journal of Organic Chemistry, 57, 2771-2771 (1992)
Thompson, W.J. et al.
Tetrahedron Letters, 33, 2957-2957 (1992)
S Thaisrivongs et al.
Journal of medicinal chemistry, 36(8), 941-952 (1993-04-16)
A number of potential HIV protease inhibitory peptides that contain the dihydroxyethylene isostere were prepared and evaluated for their enzyme binding affinity and antiviral activity in cell cultures. From the template of a previously reported active peptide A, modifications at
View All Related Papers

Chromatograms

application for HPLC

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