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188832

Sigma-Aldrich

15-Crown-5

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H20O5
CAS Number:
Molecular Weight:
220.26
Beilstein:
1618144
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.465 (lit.)

bp

93-96 °C/0.05 mmHg (lit.)

density

1.113 g/mL at 20 °C (lit.)

functional group

ether

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

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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.

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Pictograms

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Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Crown ethers for chemical analysis: A Review.
Yoshio M, et al.
Analytical Letters, 15(15), 1197-1276 (1982)
Intrinsic affinities of alkali cations for 15-crown-5 and 18-crown-6: bond dissociation energies of gas-phase M+? crown ether complexes.
More M, et al.
Journal of the American Chemical Society, 121(2), 417-423 (1999)
A PVC-based benzo-15-crown-5 membrane sensor for cadmium
Srivastava SK, et al.
Electroanalysis, 8(10), 938-940 (1996)
Mechanistic and synthetic studies in catalytic allylic alkylation with palladium complexes of 1-(2-diphenylphosphino-1-naphthyl) isoquinoline
Brown JM, et al.
Tetrahedron, 50(15), 4493-4506 (1994)
A comparative study of the structure and luminescence of mono-and dinuclear crown-ether lanthanide complexes
de Souza KMN, et al.
Journal of Luminescence, 170, 571-587 (2016)

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