(2S)-2-amino-3-phenylpropan-1-ol

• ChemBase ID: 4059
• Molecular Formular: C9H13NO
• Molecular Mass: 151.20562
• Monoisotopic Mass: 151.09971404
• SMILES: N[C@H](CO)Cc1ccccc1
• Canonical SMILES: OC[C@H](Cc1ccccc1)N
• InChI: 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
• InChIKey: STVVMTBJNDTZBF-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-phenylpropan-1-ol
• IUPAC Traditional name: L-phenylalaninol
• Synonyms: (S)-2-Amino-3-phenyl-1-propanol; L-Phenylalaninol; L-Phenylalaninol; (S)-(-)-2-Amino-3-phenyl-1-propanol; (S)-(-)-2-Amino-3-phenyl-1-propanol; H-Phe-ol; (βS)-β-Amino-benzenepropanol; ((1S)-1-Hydroxymethyl-2-phenylethyl)amine; (2S)-2-Amino-3-phenyl-1-propanol; (S)-(-)-2-Amino-3-phenyl-1-glycinol; (S)-2-Amino-1-hydroxy-3-phenylpropane; (R)-2-Amino-3-phenylpropanol; L-2-Amino-3-phenyl-1-propanol; L-2-Amino-3-phenylpropan-1-ol; (S)-(-)-2-Amino-3-phenyl-1-propanol; L-Phenylalaninol; (S)-2-Benzylethanolamine; (S)-beta-Aminobenzenepropanol; 2-Amino-3-phenyl-1-propanol; (S)-2-氨基-3-苯基-1-丙醇; L-苯丙氨醇; L-苯丙氨醇; (S)-(-)-2-氨基-3-苯基-1-丙醇; L-苯丙胺醇

Database IDs

• CAS Number: 3182-95-4
• EC Number: 221-674-4
• MDL Number: MFCD00004732
• Beilstein Number: 2208238
• PubChem SID: 24851436; 160967493; 46507788
• PubChem CID: 447213

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.116403
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.221748
• LogD (pH = 7.4): -1.2180183
• Log P: 0.7573405
• Molar Refractivity: 45.2489 cm^3
• Polarizability: 17.932344 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.61
• LOG S: -1.17
• Solubility (Water): 1.03e+01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Ethyl Acetate; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 68-70°C; 89-94°C; 90-93 °C; 92-94 °C(lit.)
• Optical Rotation: [α]20/D -23±2°, c = 5% in ethanol; [α]22/D -22.8°, c = 1.2 in 1 M HCl; -23 (c=5 in ethanol)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Air Sensitive
• RTECS: UA6900000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3259; UN3259
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3259 8/PG 3

Product Information

• Purity: ≥99.0% (NT); 98%
• Grade: puriss.
• Optical Purity: ee: 99% (HPLC); enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: C6H5CH2CH(NH2)CH2OH
• Empirical Formula (Hill Notation): C9H13NO

DETAILS

DrugBank - DB04484

Drug information: experimental

Sigma Aldrich - 190438

Packaging
1, 10 g in glass bottle
Application
Reacts with nitriles to form oxazolines which are useful in Pd-catalyzed allylic substitution.1,2 Also employed in amidation for chiral resolution3 and NADH modeling.4,5

Toronto Research Chemicals - P319520

Inhibits the intestinal absorption of Phenylalanine, making it a prospective treatment for phenylketonuria.

REFERENCES

• Shimomura, K., et al.: J. Biochem., 78, 269 (1975)
• Ambler, J., et al.: Bioorg. Med. Chem. Lett., 9, 737 (1975)