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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

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-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

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ2769
MKCP5920
MKCK7030
MKCH0795
MKCF8575

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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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