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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:
3182-95-4
Molecular Weight:
151.21
Beilstein:
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 Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

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

190438-1G:
190438-10G:
190438-BULK:
190438-VAR:

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’.

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Tetrahedron Letters, 34, 7081-7081 (1993)
Tetrahedron, 49, 5237-5237 (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)
Tripeptide LY301621 and its diastereomers as methicillin potentiators against methicillin resistant Staphylococcus aureus.
Bid CN, et al.
The Journal of Antibiotics, 50(3), 283-285 (1997)
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