(1S,2R)-2-phenylcyclopropane-1-carboxylic acid

• ChemBase ID: 90337
• Molecular Formular: C10H10O2
• Molecular Mass: 162.1852
• Monoisotopic Mass: 162.06807956
• SMILES: OC(=O)[C@@H]1[C@@H](C1)c1ccccc1
• Canonical SMILES: OC(=O)[C@H]1C[C@H]1c1ccccc1
• InChI: InChI=1S/C10H10O2/c11-10(12)9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6H2,(H,11,12)/t8-,9-/m0/s1
• InChIKey: AHDDRJBFJBDEPW-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-2-phenylcyclopropane-1-carboxylic acid
• IUPAC Traditional name: (1S,2R)-2-phenylcyclopropane-1-carboxylic acid
• Synonyms: (1R,2R)-rel-2-Phenyl-cyclopropanecarboxylic Acid; (+/-)-trans-2-Phenyl-1-cyclopropanecarboxylic Acid; NSC 40846; rac trans-2-Phenylcyclopropanecarboxylic Acid; (1R,2R)-2-Phenylcyclopropane-1-carboxylic acid; trans-2-Phenylcyclopropane-1-carboxylic acid

Database IDs

• CAS Number: 939-90-2
• MDL Number: MFCD00001292
• PubChem SID: 162077154
• PubChem CID: 736144

CALCULATED PROPERTIES

• Acid pKa: 4.537067
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.970621
• LogD (pH = 7.4): -0.8014964
• Log P: 1.9772736
• Molar Refractivity: 44.6865 cm^3
• Polarizability: 17.472937 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol
• Apperance: Off-White Solid
• Melting Point: 86-88°C

Safety Information

• Storage Warning: Irritant

DETAILS

Toronto Research Chemicals - P319685

Intermediate in the production of 2C receptor agonists.

REFERENCES

• Mahindroo, N., et al.: J. Med. Chem., 52, 4277 (2009)