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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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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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)
Márkó Grabarics et al.
The Analyst, 145(19), 6313-6333 (2020-07-28)
In the past decade, ion mobility spectrometry (IMS) in combination with mass spectrometry (IM-MS) became a widely employed technique for the separation and structural characterization of ionic species in the gas phase. Similarly to chromatography, where studies on the mechanism
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