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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:
33100-27-5
Molecular Weight:
220.26
Beilstein:
1618144
EC Number:
251-379-6
MDL number:
MFCD00005110
UNSPSC Code:
12352005
PubChem Substance ID:
24851323
NACRES:
NA.22
Pricing and availability is not currently available.

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.[1] 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.[2][3][4]

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).[4]  
  • In the allylic alkylation of allyl acetates by malonates with palladium complex catalysts.[5]

15-Crown-5 is a crown ether that is generally used as a ligand in coordination chemistry.[6] It shows the ability to complexes with alkali metal ions.[7][8]

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Product No.
Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8186
BCCM8187
BCCL6997
BCCJ9009
BCCJ3924

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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)
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 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)
15-Crown-5.
Parsons S, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(7), o3130-o3130 (2007)
View All Related Papers

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Is the 15-crown-5 ether packaged under inert atmosphere?

    1 answer

    1. Product 188832 is packaged under inert gas. It is recommended to store under inert gas, as well.

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