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

• ChemBase ID: 19291
• Molecular Formular: C9H13NO
• Molecular Mass: 151.20562
• Monoisotopic Mass: 151.09971404
• SMILES: C(c1ccccc1)[C@@H](N)CO
• 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-/m1/s1
• InChIKey: STVVMTBJNDTZBF-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-phenylpropan-1-ol
• IUPAC Traditional name: (R)-2-amino-3-phenylpropanol
• Synonyms: (R)-2-Amino-3-phenylpropan-1-ol; (βR)-β-Amino-benzenepropanol; D-2-Amino-3-phenyl-1-propanol; ((1R)-1-Hydroxymethyl-2-phenylethyl)amine; (2R)-2-Amino-3-phenyl-1-propanol; (R)-(+)-2-Amino-3-phenyl-1-glycinol; (R)-2-Amino-1-hydroxy-3-phenylpropane; (R)-2-Benzylethanolamine; D-Phenylalaninol; (R)-(+)-2-Amino-3-phenyl-1-propanol; (R)-2-Amino-3-phenyl-1-propanol; D-Phenylalaninol; (R)-2-Amino-3-phenyl-propan-1-ol; D-Phenylalaninol; (2R)-2-Amino-1-hydroxy-3-phenylpropane; (2R)-2-Amino-3-phenylpropan-1-ol; (R)-(+)-2-Amino-3-phenyl-1-propanol; H-D-Phe-ol; D-苯丙氨醇; (R)-(+)-2-氨基-3-苯基-1-丙醇; (R)-2-氨基-3-苯基-1-丙醇; D-苯丙氨醇

Database IDs

• CAS Number: 5267-64-1
• EC Number: 226-086-1
• MDL Number: MFCD00064298
• Beilstein Number: 4665408; 2208239
• PubChem SID: 24887259; 24857160; 160982598
• PubChem CID: 853475

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Light Yellow Solid
• Melting Point: 89-94°C; 89-95°C; 91-92 °C; 92-93°C; 93-95 °C(lit.)
• Optical Rotation: [α]/D +22.8°, c = 1.2 in 1 M HCl; [α]20/D +23±2°, c = 5% in ethanol; +23 2 (c=5 in ethanol)

Safety Information

• Storage Warning: Air Sensitive; Corrosive/Air Sensitive/Store under Argon; IRRITANT
• 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: false; 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: ≥97.0% (NT); 95%; 98%
• Grade: purum
• Optical Purity: enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: C6H5CH2CH(NH2)CH2OH
• Empirical Formula (Hill Notation): C9H13NO

DETAILS

Sigma Aldrich - 284491

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 78115

Other Notes
Chiral β-amino alcohol; oxidation of the N-protected compound to the aldehyde1; Resolving agent for acids and aldehydes2,3; The corresponding oxazolidinone is used as auxiliary in stereocontrolled aldol and alkylation reactions4,5

Toronto Research Chemicals - P319515

Enantiomer of L-Phenylalaninol, an inhibitor of intestinal Phenylalanine absorption.

REFERENCES

• Myllymaki, M., et al.: Eur. J. Med. Chem., 44, 4179 (2009)
• Whitby, L., et al.; Bioorg. Med. Chem. Lett., 19, 3771 (2009)
• Has been used as a chiral auxiliary for asymmetric Michael reactions: J. Org. Chem., 50, 3863 (1985).