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188832

Sigma-Aldrich

15-Crown-5

98%

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Synonym(s):
15C5, 1,4,7,10,13-Pentaoxacyclopentadecane
Empirical Formula (Hill Notation):
C10H20O5
CAS Number:
Molecular Weight:
220.26
Beilstein/REAXYS Number:
1618144
EC Number:
MDL number:
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.)

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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1 of 4

This Item
274984282790388424
15-Crown-5 98%

188832

15-Crown-5

18-Crown-6 ≥99.0%

274984

18-Crown-6

Benzo-15-crown-5 98%

282790

Benzo-15-crown-5

2-Hydroxymethyl-15-crown-5 95%

388424

2-Hydroxymethyl-15-crown-5

bp

93-96 °C/0.05 mmHg (lit.)

bp

-

bp

-

bp

135 °C/1.5 mmHg (lit.)

density

1.113 g/mL at 20 °C (lit.)

density

-

density

-

density

1.175 g/mL at 25 °C (lit.)

refractive index

n20/D 1.465 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.479 (lit.)

form

liquid

form

solid

form

-

form

viscous liquid

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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Description
Pricing

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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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)
Crown ethers for chemical analysis: A Review.
Yoshio M, et al.
Analytical Letters, 15(15), 1197-1276 (1982)
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 PVC-based benzo-15-crown-5 membrane sensor for cadmium
Srivastava SK, et al.
Electroanalysis, 8(10), 938-940 (1996)
15-Crown-5.
Parsons S, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(7), o3130-o3130 (2007)

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