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Merck
CN

15145

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

≥98.0% (AT)

Synonym(s):

(−)-Bis[(S)-α-methylbenzyl]amine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C16H19N · HCl
CAS Number:
40648-92-8
Molecular Weight:
261.79
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
57647325
MDL number:
MFCD00216671
Beilstein/REAXYS Number:
4723969

Key Documents

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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

SMILES string

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

InChI key

ZBQCLJZOKDRAOW-IODNYQNNSA-N

assay

≥98.0% (AT)

form

solid

optical activity

[α]20/D −73±2°, c = 3% in ethanol

mp

~260 °C

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.

Other Notes

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW7771
BCBL3348V
1393865
1255184
1265053

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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)
N.S. Simpkins
Chemical Society Reviews, 19, 335-335 (1990)
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