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190438

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:
Molecular Weight:
151.21
Beilstein:
2208238
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

functional group

amine
hydroxyl
phenyl

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

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 Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 34, 2015-2015 (1993)
Chiral supramolecular metal-organic architectures from dinuclear copper complexes.
Pradeep CP and Das SK.
Polyhedron, 28(3), 630-636 (2009)
Tetrahedron, 49, 5237-5237 (1993)
Tetrahedron Letters, 34, 7081-7081 (1993)
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)

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