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331880

Sigma-Aldrich

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

99%

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About This Item

Linear Formula:
C6H5CH(NH2)CH(C6H5)OH
CAS Number:
23364-44-5
Molecular Weight:
213.28
Beilstein:
1212828
MDL number:
MFCD00074959
UNSPSC Code:
12352116
PubChem Substance ID:
24860005
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

optical activity

[α]25/D +7.0°, c = 0.6 in ethanol

mp

142-144 °C (lit.)

functional group

amine
hydroxyl
phenyl

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

331880-5G:
331880-VAR:
331880-1G:
331880-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM8476
MKCD5667
MKBZ7001V
MKBT4099V
MKBS8908V

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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)
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)
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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