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Sigma-Aldrich

(S)-(−)-2-Amino-3-phenyl-1-propanol

98%, optical purity ee: 99% (HPLC)

Synonym(s):

L-Phenylalaninol

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About This Item

Linear Formula:
C6H5CH2CH(NH2)CH2OH
CAS Number:
3182-95-4
Molecular Weight:
151.21
Beilstein/REAXYS Number:
2208238
EC Number:
221-674-4
MDL number:
MFCD00004732
UNSPSC Code:
12352116
PubChem Substance ID:
24851436
NACRES:
NA.22

assay

98%

form

solid

optical activity

[α]22/D −22.8°, c = 1.2 in 1 M HCl

optical purity

ee: 99% (HPLC)

mp

92-94 °C (lit.)

SMILES string

N[C@H](CO)Cc1ccccc1

InChI

1S/C9H13NO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2/t9-/m0/s1

InChI key

STVVMTBJNDTZBF-VIFPVBQESA-N

Related Categories

General description

(S)-(-)-2-Amino-3-phenyl-1-propanol is a chiral amino alcohol.

Application

(S)-(-)-2-Amino-3-phenyl-1-propanol can undergo condensation with 5-nitro­salicylaldehyde to form (S)-2-[(1-benzyl-2-hydroxy­ethyl­imino)meth­yl]-4-nitro­phenol, a new chiral Schiff base. It reacts with substituted salicylaldehydes to form tridentate chiral Schiff base ligands, which can form H-bonded chiral supramolecular metal-organic architectures. It can also be used in the synthesis of an unnatural tripeptide, which can enhance the antimicrobial activity of methicillin against methicillin resistant Staphylococcus aureus.
Reacts with nitriles to form oxazolines which are useful in Pd-catalyzed allylic substitution. Also employed in amidation for chiral resolution and NADH modeling.

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Intramolecular hydrogen transfer in (S)-2-[(1-benzyl-2-hydroxyethylimino) methyl]-4-nitrophenol, a new chiral Schiff base.
Pradeep CP.
Acta Crystallographica Section E, Structure Reports Online, 61(11), o3825-o3827 (2005)
Tetrahedron Letters, 34, 7081-7081 (1993)
Chiral supramolecular metal-organic architectures from dinuclear copper complexes.
Pradeep CP and Das SK.
Polyhedron, 28(3), 630-636 (2009)
Tetrahedron Letters, 34, 2015-2015 (1993)
Violetta Constantinou-Kokotou et al.
Journal of peptide science : an official publication of the European Peptide Society, 11(7), 431-435 (2005-01-07)
2-Oxoamides based on long chain beta-amino acids were synthesized. 1-Benzyl substituted long chain amines, needed for such synthesis, were synthesized starting from Boc-phenylalaninol. The oxidative conversion of a phenyl group to a carboxyl group was used as the key transformation
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