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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/REAXYS Number:
1363064
EC Number:
206-036-5
MDL number:
MFCD00005103
UNSPSC Code:
12352005
PubChem Substance ID:
24851661
NACRES:
NA.22

Quality Level

100

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.)

functional group

ether

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

signalword

Danger

hcodes

H330

Hazard Classifications

Acute Tox. 1 Inhalation

Storage Class

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

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL2187
MKCL0309
MKCD8846
MKBV7773V
MKBS0785V

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Ana I Ojeda-Amador et al.
Dalton transactions (Cambridge, England : 2003), 46(19), 6392-6403 (2017-05-04)
The structural chemistry of eleven donor complexes of the important Brønsted base potassium 1,1,1,3,3,3-hexamethyldisilazide (KHMDS) has been studied. Depending on the donor, each complex adopted one of five general structural motifs. Specifically, in this study the donors employed were toluene
Preparation of poly (diethylsiloxane) with the NaOH/12-crown-4 catalyst
Hedden RC and Cohen C
Polymer, 41(18), 6975-6979 (2000)
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
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.
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)
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