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190438 Sigma-Aldrich

(S)-(−)-2-Amino-3-phenyl-1-propanol

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

Synonym: L-Phenylalaninol

  • CAS Number 3182-95-4

  • Linear Formula C6H5CH2CH(NH2)CH2OH

  • Molecular Weight 151.21

  •  Beilstein/REAXYS Number 2208238

  •  EC Number 221-674-4

  •  MDL number MFCD00004732

  •  PubChem Substance ID 24851436

  •  NACRES NA.22

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Properties

Related Categories Amino Alcohols, Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Organic Building Blocks More...
InChI Key   STVVMTBJNDTZBF-VIFPVBQESA-N
assay   98%
optical activity   [α]22/D −22.8°, c = 1.2 in 1 M HCl
optical purity   ee: 99% (HPLC)
mp   92-94 °C (lit.)

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.

Packaging

1, 10 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3259PSN1 8 / PGIII
WGK Germany 
3
RTECS 
UA6900000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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