Skip to Content
MilliporeSigma
All Photos(1)

Documents

190438

Sigma-Aldrich

(S)-(−)-2-Amino-3-phenyl-1-propanol

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

Sign Into View Organizational & Contract Pricing

Synonym(s):
L-Phenylalaninol
Linear Formula:
C6H5CH2CH(NH2)CH2OH
CAS Number:
Molecular Weight:
151.21
Beilstein/REAXYS Number:
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.)

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.

wgk_germany

WGK 3

ppe

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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service