440868

(R)-(+)-3-Chlorostyrene oxide

98%

• Synonym(s): (R)-(+)-(3-Chlorophenyl)oxirane
• Empirical Formula (Hill Notation): C₈H₇ClO
• CAS Number: 62600-71-9
• Molecular Weight: 154.59
• MDL number: MFCD00673317
• UNSPSC Code: 12352000

Properties

• assay: 98%
• optical activity: [α]20/D +21°, neat
• refractive index: n20/D 1.551 (lit.)
• bp: 67-68 °C/1 mmHg (lit.)
• density: 1.214 g/mL at 25 °C (lit.)
• SMILES string: Clc1cccc(c1)[C@@H]2CO2
• InChI: 1S/C8H7ClO/c9-7-3-1-2-6(4-7)8-5-10-8/h1-4,8H,5H2/t8-/m0/s1
• InChI key: YVMKRPGFBQGEBF-QMMMGPOBSA-N

Description

Application

Key chiral synthon for the preparation of the potent antidiabetic and antiobesity agent CL-316,243, a benzodioxole-containing phenethanolamine.[1] Ring opening of this chiral epoxide with amines produces amino alcohols which have been used as β-adrenergic agonists.[2]

Reactant involved in:

• Diastereoselective Wadsworth-Emmons cyclopropanation for synthesis of quaternaty cyclopropyl esters
• Synthesis of phenylethanolamine derivatives as β3-adrenergic receptor agonists
• Stereoselective ring-opening for synthesis of β-aryloxy-substituted alcohols and amines
• Synthesis of Biphenyl benzoic acid derivatives as β3-adrenergic receptor agonists
• Synthesis of (S)-2-, 3-, and 4-chlorostyrene oxides with epoxide hydrolase