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331899

Sigma-Aldrich

(1R,2S)-(−)-2-Amino-1,2-diphenylethanol

99%

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About This Item

Linear Formula:
C6H5CH(NH2)CH(C6H5)OH
CAS Number:
23190-16-1
Molecular Weight:
213.28
Beilstein:
2806218
MDL number:
MFCD00074960
UNSPSC Code:
12352116
PubChem Substance ID:
24860006
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]25/D −7.0°, c = 0.6 in ethanol

mp

142-144 °C (lit.)

SMILES string

N[C@H]([C@H](O)c1ccccc1)c2ccccc2

InChI

1S/C14H15NO/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14,16H,15H2/t13-,14+/m0/s1

InChI key

GEJJWYZZKKKSEV-UONOGXRCSA-N

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Application

Chiral auxiliary used for Pd(II)-assisted chiral tandem alkylation and carbonylative coupling reactions.

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
MKCP2851
MKBS5389V
MKBJ5597V
MKBG4279V
MKBD4359

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J.J. Masters et al.
The Journal of Organic Chemistry, 58, 4547-4547 (1993)
J.J. Masters et al.
The Journal of Organic Chemistry, 56, 5666-5666 (1991)
Michael L Berger et al.
Bioorganic & medicinal chemistry, 17(9), 3456-3462 (2009-04-07)
We resolved 1,2-diphenylethylamine (DPEA) into its (S)- and (R)-enantiomer and used them as precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine, flexible homeomorphs of the NMDA channel blocker MK-801. We also describe the synthesis of the dicyclohexyl analogues of DPEA. These

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