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

• Quality Level: 100
• 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

Description

General description

(S)-(-)-2-Amino-3-phenyl-1-propanol is a chiral amino alcohol.[1]

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.[2] It reacts with substituted salicylaldehydes to form tridentate chiral Schiff base ligands, which can form H-bonded chiral supramolecular metal-organic architectures.[1] 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.[3]

Reacts with nitriles to form oxazolines which are useful in Pd-catalyzed allylic substitution.[4][5] Also employed in amidation for chiral resolution[6] and NADH modeling.[7][8]

Safety Information

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