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331880

Sigma-Aldrich

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

99%

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Linear Formula:
C6H5CH(NH2)CH(C6H5)OH
CAS Number:
23364-44-5
Molecular Weight:
213.28
Beilstein:
1212828
MDL number:
MFCD00074959
PubChem Substance ID:
24860005
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+/m1/s1

InChI key

GEJJWYZZKKKSEV-KGLIPLIRSA-N

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Application

(1S,2R)-(+)-2-Amino-1,2-diphenylethanol can be used:
  • To prepare vanadium(V) Schiff base complexes, which are used as catalysts in the oxidation of sulfides and olefins.
  • To prepare chiral selectors, which are immobilized on aminated silica gel, applicable as chiral stationary phase in HPLC.
  • To immobilize on the frame of α-zirconium phosphate to yield layered zirconium phosphonates, which are used in the heterogeneous catalysis.
  • As a chiral auxiliary in the preparation of homopropargylic alcohols from aliphatic and aromatic aldehydes.

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

Regulatory Information

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Vanadium (V) complexes with chiral tridentate Schiff base ligands derived from 1S, 2R (+)-2-amino-1, 2-diphenylethanol and with acetohydroxamate co-ligand: Synthesis, characterization and catalytic activity in the oxidation of prochiral sulfides and olefins
Romanowski G, et al.
J. Mol. Catal. A: Chem., 381, 148-160 (2014)
Zirconium phosphonate immobilized chiral amino alcohol for heterogeneous enantioselective addition of diethylzinc to benzaldehyde
Zheng B, et al.
Catalysis Communications, 8(12), 1923-1928 (2007)
Asymmetric indium-mediated synthesis of homopropargylic alcohols
Hirayama LC, et al.
Tetrahedron Letters, 47(29), 5173-5176 (2006)
Chuan-Qi Yin et al.
Chirality, 21(4), 442-448 (2008-07-26)
A chiral selector was prepared through the reaction between (1S,2R)-(+)-2-amino-1,2-diphenylethanol and phenyl isocyanate. This selector was immobilized on aminated silica gel, respectively, with bifunctional group linkers of 1,4-phenylene diisocyanate, methylene-di-p-phenyl diisocyanate, and terephthaloyl chloride to produce corresponding three chiral stationary
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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