(2R)-2-(3-chlorophenyl)oxirane

• ChemBase ID: 77520
• Molecular Formular: C8H7ClO
• Molecular Mass: 154.59358
• Monoisotopic Mass: 154.01854252
• SMILES: O1C[C@H]1c1cc(ccc1)Cl
• Canonical SMILES: Clc1cccc(c1)[C@@H]1CO1
• InChI: InChI=1S/C8H7ClO/c9-7-3-1-2-6(4-7)8-5-10-8/h1-4,8H,5H2/t8-/m0/s1
• InChIKey: YVMKRPGFBQGEBF-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(3-chlorophenyl)oxirane
• IUPAC Traditional name: (2R)-2-(3-chlorophenyl)oxirane
• Synonyms: (R)-(3-Chlorophenyl)oxirane; (R)-(+)-3-Chlorostyrene oxide 99%; (R)-(+)-(3-Chlorophenyl)oxirane; (R)-(+)-3-Chlorostyrene oxide; (R)-(+)-3-Chlorostyrene oxide; (R)-(+)-(3-Chlorophenyl)oxirane; (R)-(+)-(3-氯苯基)环氧乙烷; (R)-(+)-3-氯环氧苯乙烷

Database IDs

• CAS Number: 62600-71-9
• MDL Number: MFCD00673317
• Beilstein Number: 3588590
• PubChem SID: 162042392; 24855719; 24880095
• PubChem CID: 10898919

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.3413093
• LogD (pH = 7.4): 2.3413093
• Log P: 2.3413093
• Molar Refractivity: 40.1311 cm^3
• Polarizability: 15.834716 Å^3
• Polar Surface Area: 12.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 67-68 °C/1 mmHg(lit.)
• Flash Point: 206.6 °F; 97 °C
• Density: 1.214 g/mL at 25 °C(lit.); 1.217 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.551; n20/D 1.551(lit.)
• Optical Rotation: [α]20/D +19°, neat; [α]20/D +21°, neat; [α]20/D -11.7±2°, c = 1.8% in chloroform

Safety Information

• Storage Warning: Irritant/Moisture Sensitive/Store under Nitrogen
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥95.0% (HPLC); ≥97.5% (GC); 98%
• Grade: produced by BASF; purum
• Optical Purity: enantiomeric excess: ≥97.5%
• Empirical Formula (Hill Notation): C8H7ClO

DETAILS

Sigma Aldrich - 726699

Packaging
5, 25 g in glass bottle
Legal Information
ChiPros is a registered trademark of BASF SE

Sigma Aldrich - 440868

Application
Key chiral synthon for the preparation of the potent antidiabetic and antiobesity agent CL-316,243, a benzodioxole-containing phenethanolamine.8 Ring opening of this chiral epoxide with amines produces amino alcohols which have been used as β-adrenergic agonists.9
Reactant involved in:
• Diastereoselective Wadsworth-Emmons cyclopropanation for synthesis of quaternaty cyclopropyl esters1
• Synthesis of phenylethanolamine derivatives as β3-adrenergic receptor agonists2,3
• Stereoselective ring-opening for synthesis of β-aryloxy-substituted alcohols and amines4
• Synthesis of Biphenyl benzoic acid derivatives as β3-adrenergic receptor agonists5,6
• Synthesis of (S)-2-, 3-, and 4-chlorostyrene oxides with epoxide hydrolase7

Sigma Aldrich - 563382

Packaging
1 g in glass bottle
Application
Reactant involved in:
• Diastereoselective Wadsworth-Emmons cyclopropanation for synthesis of quaternaty cyclopropyl esters1
• Synthesis of phenylethanolamine derivatives as β3-adrenergic receptor agonists2,3
• Stereoselective ring-opening for synthesis of β-aryloxy-substituted alcohols and amines4
• Synthesis of Biphenyl benzoic acid derivatives as β3-adrenergic receptor agonists5,6
• Synthesis of (S)-2-, 3-, and 4-chlorostyrene oxides with epoxide hydrolase7

Sigma Aldrich - 26008

Other Notes
Chiral building block; preparation of a novel β-adrenergic agonist1,2