190438

(S)-(−)-2-Amino-3-phenyl-1-propanol

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

• Synonym(s): L-Phenylalaninol
• 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

Properties

• 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

Description

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.

Safety Information

• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves