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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

Pricing and availability is not currently available.

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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1 of 4

This Item
PHR3192L012900019346
Lactitol United States Pharmacopeia (USP) Reference Standard

1356687

Lactitol

Lactitol pharmaceutical secondary standard, certified reference material

PHR3192

Lactitol

Lactitol analytical standard

19346

Lactitol

grade

pharmaceutical primary standard

grade

certified reference material, pharmaceutical secondary standard

grade

pharmaceutical primary standard

grade

analytical standard

format

neat

format

-

format

neat

format

neat

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical

application(s)

pharmaceutical (small molecule)

application(s)

cleaning products
cosmetics
food and beverages
personal care

API family

lactitol

API family

lactitol

API family

lactitol

API family

-

mp

95-98 °C (lit.)

mp

95-98 °C (lit.)

mp

95-98 °C (lit.)

mp

-

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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Pictograms

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Signal Word

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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