(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine; (2R)-2-hydroxy-2-phenylacetic acid

• ChemBase ID: 167375
• Molecular Formular: C17H17F2NO3
• Molecular Mass: 321.3185864
• Monoisotopic Mass: 321.11764985
• SMILES: c1cc(c(cc1[C@H]1[C@@H](C1)N)F)F.c1cccc(c1)[C@@H](O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](c1ccccc1)O.N[C@@H]1C[C@H]1c1ccc(c(c1)F)F
• InChI: InChI=1S/C9H9F2N.C8H8O3/c10-7-2-1-5(3-8(7)11)6-4-9(6)12;9-7(8(10)11)6-4-2-1-3-5-6/h1-3,6,9H,4,12H2;1-5,7,9H,(H,10,11)/t6-,9+;7-/m01/s1
• InChIKey: GUESUQPLVFMJIT-KLTOLQSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine; (2R)-2-hydroxy-2-phenylacetic acid
• IUPAC Traditional name: (-)-mandelic acid; (1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine
• Synonyms: (αR)-α-Hydroxybenzeneacetic Acid compd. with (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine; (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate

Database IDs

• CAS Number: 376608-71-8
• PubChem SID: 162261508
• PubChem CID: 9944965

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.3724298
• LogD (pH = 7.4): -0.5111565
• Log P: 1.6242863
• Molar Refractivity: 42.1294 cm^3
• Polarizability: 15.938919 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 158-162°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D446035

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine is an intermediate in the preparation of orally active reversible P2Y12 receptor antagonists for the prevention of thrombosis.

REFERENCES

• Springthorpe, B. et al.: Bioorg. Med. Chem. Lett., 17, 6013 (2007)