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188832 Sigma-Aldrich

15-Crown-5

98%

Synonym: 1,4,7,10,13-Pentaoxacyclopentadecane, 15C5

  • CAS Number 33100-27-5

  • Empirical Formula (Hill Notation) C10H20O5

  • Molecular Weight 220.26

  •  Beilstein/REAXYS Number 1618144

  •  EC Number 251-379-6

  •  MDL number MFCD00005110

  •  PubChem Substance ID 24851323

  •  NACRES NA.22

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Properties

Related Categories Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Synthetic Reagents
Quality Level   200
assay   98%
refractive index   n20/D 1.465 (lit.)
bp   93-96 °C/0.05 mmHg (lit.)
density   1.113 g/mL at 20 °C (lit.)
SMILES string   O1CCOCCOCCOCCOCC1
InChI   1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
InChI key   VFTFKUDGYRBSAL-UHFFFAOYSA-N

Description

General description

15-Crown-5 is a crown ether generally used as a ligand in coordination chemistry because of its strong chelating property with certain alkali cations to form complexes. Some derivatives of 15-crown-5 are used as sensors and probes in different physical-chemical processes, phase-transfer reactions, and selective capture of ions for separation and transport.

Application

15-Crown-5 can be used:     
•  As a phase transfer catalyst for the preparation of polyphenylacetylene (PPA) by anionic polymerization of phenylacetylene with sodium amide (NaNH2).  
•  In the allylic alkylation of allyl acetates by malonates with palladium complex catalysts.

15-Crown-5 is a crown ether that is generally used as a ligand in coordination chemistry. It shows the ability to complexes with alkali metal ions.

Packaging

1, 5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
SB0200000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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901584 15-Crown-5 solution, 1 M in THF

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