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15145

Sigma-Aldrich

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

≥98.0% (AT)

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Synonym(s):
(−)-Bis[(S)-α-methylbenzyl]amine hydrochloride
Empirical Formula (Hill Notation):
C16H19N · HCl
CAS Number:
40648-92-8
Molecular Weight:
261.79
Beilstein:
4723969
MDL number:
MFCD00216671
UNSPSC Code:
12352116
PubChem Substance ID:
57647325
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.

Other Notes

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

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

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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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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