190438
(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
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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
Certificates of Analysis (COA)
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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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