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15145

Sigma-Aldrich

(−)-Bis[(S)-1-phenylethyl]amine hydrochloride

≥98.0% (AT)

Synonym(s):
(−)-Bis[(S)-α-methylbenzyl]amine hydrochloride
Empirical Formula (Hill Notation):
C16H19N · HCl
CAS Number:
Molecular Weight:
261.79
Beilstein:
4723969
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

≥98.0% (AT)

form

solid

optical activity

[α]20/D −73±2°, c = 3% in ethanol

mp

~260 °C

SMILES string

Cl.C[C@H](N[C@@H](C)c1ccccc1)c2ccccc2

InChI

1S/C16H19N.ClH/c1-13(15-9-5-3-6-10-15)17-14(2)16-11-7-4-8-12-16;/h3-14,17H,1-2H3;1H/t13-,14-;/m0./s1

InChI key

ZBQCLJZOKDRAOW-IODNYQNNSA-N

Application

(−)-Bis[(S)-1-phenylethyl]amine hydrochloride can be used:
  • To prepare phosphoramidite (Feringa) ligand named (R)-2,2′-binaphthoyl-(S,S)-di-(1-phenylethyl)aminoylphosphine.
  • As a chiral amphiphilic cation to encapsulate polyoxometalates, which act as supramolecular assemblies employed in the asymmetric oxidation of sulfides.
  • As a chiral shift agent in the determination of enantiomeric purity of tris(tetrachlorobenzenediolato) phosphate(V) anion using 31P NMR.

Packaging

5, 25 g in glass bottle

Other Notes

The corresponding chiral lithium amide is used as base for the enantioselective deprotonation of ketones.

Certificate of Analysis

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Certificate of Origin

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More documents

Quotes and Ordering

Supramolecular assembly of chiral polyoxometalate complexes for asymmetric catalytic oxidation of thioethers
Wang Y, et al.
Journal of Materials Chemistry, 22(18), 9181-9188 (2012)
Large-scale synthesis and resolution of trisphat [tris (tetrachlorobenzenediolato) phosphate (v)] anion
Favarger F, et al.
The Journal of Organic Chemistry, 69(24), 8521-8524 (2004)
P.J. Cox et al.
Tetrahedron Asymmetry, 2, 1-1 (1991)
(R)-2, 2′-Binaphthoyl-(S, S)-DI (1-phenylethyl) aminophosphine. Scalable protocols for the syntheses of phosphoramidite (feringa) ligands
Smith CR, et al.
Organic Syntheses, 85, 238-238 (2008)
T. Honda et al.
Tetrahedron Asymmetry, 4, 1475-1475 (1993)

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