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194905

Sigma-Aldrich

12-Crown-4

98%

Synonym(s):

1,4,7,10-Tetraoxacyclododecane

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About This Item

Empirical Formula (Hill Notation):
C8H16O4
CAS Number:
294-93-9
Molecular Weight:
176.21
Beilstein:
1363064
EC Number:
206-036-5
MDL number:
MFCD00005103
UNSPSC Code:
12352005
PubChem Substance ID:
24851661
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.463 (lit.)

bp

61-70 °C/0.5 mmHg (lit.)

mp

16 °C (lit.)

density

1.089 g/mL at 25 °C (lit.)

SMILES string

C1COCCOCCOCCO1

InChI

1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2

InChI key

XQQZRZQVBFHBHL-UHFFFAOYSA-N

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General description

12-Crown-4 is a crown ether generally used as a ligand in coordination chemistry. It is also known as lithium ionophore because of its strong chelating property specific to lithium cation.

Application

12-Crown-4 can be used as:
  • A promoter in the synthesis of poly(diethylsiloxane) (PDES) from monomer hexaethylcyclotrisiloxane using NaOH as a catalyst via anionic ring-opening polymerization.
  • As an additive in the preparation of triarylmethane derivatives by palladium-catalyzed cross coupling reaction of aryl bromides with diarylmethane derivatives.
  • A phase transfer catalyst in organic synthesis.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H330

Hazard Classifications

Acute Tox. 1 Inhalation

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Preparation of poly (diethylsiloxane) with the NaOH/12-crown-4 catalyst
Hedden RC and Cohen C
Polymer, 41(18), 6975-6979 (2000)
Zehra Edis et al.
Pathogens (Basel, Switzerland), 8(4) (2019-10-30)
Antimicrobial agents containing symmetrical triiodides complexes with halogen bonding may release free iodine molecules in a controlled manner. This happens due to interactions with the plasma membrane of microorganisms which lead to changes in the structure of the triiodide anion.
Mazhar Ali Abbasi et al.
Sensors (Basel, Switzerland), 12(11), 15424-15437 (2012-12-04)
In this study honeycomb-like NiO nanostructures were grown on nickel foam by a simple hydrothermal growth method. The NiO nanostructures were characterized by field emission electron microscopy (FESEM), high resolution transmission electron microscopy (HRTEM) and X-ray diffraction (XRD) techniques. The
Multilayered ion-imprinted membranes with high selectivity towards Li+ based on the synergistic effect of 12-crown-4 and polyether sulfone
Lu J, et al.
Applied Surface Science, 427, 931-941 (2018)
Changna Yin et al.
Rapid communications in mass spectrometry : RCM, 34(9), e8719-e8719 (2020-01-04)
The poly(ethylene oxide) (PEO)-alkali metal cation interaction is widely used in many areas. The conformation of the PEO-alkali metal cation complex has been studied extensively, but the conformational mechanism is still unclear. Simulations have been used to explain the mechanism
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