194905
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:
Molecular Weight:
176.21
Beilstein:
1363064
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
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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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