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563382

Sigma-Aldrich

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

Synonym(s):

(R)-(+)-(3-Chlorophenyl)oxirane

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About This Item

Empirical Formula (Hill Notation):
C8H7ClO
CAS Number:
62600-71-9
Molecular Weight:
154.59
MDL number:
MFCD00673317
UNSPSC Code:
12352005
PubChem Substance ID:
24880095
NACRES:
NA.22

optical activity

[α]20/D +19°, neat

refractive index

n20/D 1.551 (lit.)

bp

67-68 °C/1 mmHg (lit.)

density

1.214 g/mL at 25 °C (lit.)

functional group

chloro
ether

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

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Application

(R)-(+)-3-Chlorostyrene oxide may be used as an intermediate for the synthesis of 4-aminopiperidine based human β3-adrenergic receptor (AR) agonists.
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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

206.6 °F - closed cup

Flash Point(C)

97 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
12717CE
09008CE
06614MD
11001LD
04518KD

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4-Aminopiperidine ureas as potent selective agonists of the human ? 3-Adrenergic receptor.
Ashwell MA, et al.
Bioorganic & Medicinal Chemistry Letters, 11(24), 3123-3127 (2001)

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