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663336

Sigma-Aldrich

(1R,2R)-(−)-trans-1-Amino-2-indanol

97%

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About This Item

Empirical Formula (Hill Notation):
C9H11NO
CAS Number:
163061-73-2
Molecular Weight:
149.19
MDL number:
MFCD08275447
UNSPSC Code:
12352116
PubChem Substance ID:
24884630
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

optical activity

[α]/D -23.0°, c = 1 in ethanol

mp

142-146 °C

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-RKDXNWHRSA-N

Application

(1R,2R)-(−)-trans-1-Amino-2-indanol has been used as a starting material to prepare an indene-based chiral auxiliary, which is used in the aldol reaction.
It can also be used as:
  • A starting material in the synthesis of oxazoline-alcohol ligands, which are employed in the asymmetric addition reaction of diethylzinc to aldehydes.
  • A chiral test compound in the study of enantiomeric separation of chiral primary amines using supercritical fluid chromatography (SFC) and HPLC.

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

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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Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions
Osorio-Lozada A and Olivo HF
Organic Letters, 10(4), 617-620 (2008)
Comparison of enantiomeric separations and screening protocols for chiral primary amines by SFC and HPLC
Armstrong DW, et al.
LCGC North America, 32(17), 742-752 (2014)
Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement
Noel T, et al.
Tetrahedron Asymmetry, 20(17), 1962-1968 (2009)

Chromatograms

application for HPLC

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