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Merck

253197

Sigma-Aldrich

Dibenzo-24-crown-8

98%

Sinónimos:

2,3,14,15-Dibenzo-1,4,7,10,13,16,19,22-octaoxacyclotetracosa-2,14-diene, 6,7,9,10,12,13,20,21,23,24,26,27-Dodecahydrodibenz[b,n]-1,4,7,10,13,16,19,22-octaoxacyclotetracosane

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About This Item

Fórmula empírica (notación de Hill):
C24H32O8
Número de CAS:
Peso molecular:
448.51
Beilstein/REAXYS Number:
1693744
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

103-105 °C (lit.)

functional group

ether

SMILES string

C1COCCOc2ccccc2OCCOCCOCCOc3ccccc3OCCO1

InChI

1S/C24H32O8/c1-2-6-22-21(5-1)29-17-13-25-9-10-27-15-19-31-23-7-3-4-8-24(23)32-20-16-28-12-11-26-14-18-30-22/h1-8H,9-20H2

InChI key

UNTITLLXXOKDTB-UHFFFAOYSA-N

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General description

Dibenzo-24-crown-8 is a macrocyclic compound that is used as a versatile reagent in organic synthesis due to its ability to form complexes with metal ions and enhance their solubility and reactivity. It is also used as a phase-transfer catalyst in various organic reactions, such as the synthesis of organic carbonates and the alkylation of phenols.

Application

Dibenzo-24-crown-8 can be used as a molecular transporter in the formation of [1]rotaxanes with thiazolium-based mono- and tris-branched ammonium ions. It is also used as a co-solvent and phase-transfer catalyst for cesium fluoride, to the development of a more efficient anhydrous fluorinating system for organic synthesis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Nozar Moradi et al.
Analytica chimica acta, 1108, 118-128 (2020-03-31)
Most attributes of the bulk materials, especially in the solid-state, are directly dictated by a manner by which the molecules are ordered. Thus, it is expected that the possibility of controlling these structural orders would allow predominating some particular physical
Mateusz Woźny et al.
Dalton transactions (Cambridge, England : 2003), 48(19), 6546-6557 (2019-04-24)
[2]rotaxanes composed of a dibenzo-24-crown-8 wheel (DB24C8) and an axle containing two metal-complexing tetraazamacrocyclic units linked with a p-xylylene bridge, coordinating the same or different metal ions (Ni and/or Cu) are described. A symmetric di-Ni rotaxane crystallizes in the monoclinic
T Gallagher et al.
Acta crystallographica. Section B, Structural science, 47 ( Pt 3), 362-368 (1991-06-01)
The crystal structures of the dipotassium and the mixed sodium/potassium picrate complexes with the crown ether dibenzo-24-crown-8 (DB24C8) were solved and found to be nearly identical. (I): NaK-pic2(DB24C8), [NaK(C6H2N3O7)2(C24H32O8)]. Mr = 966.8, triclinic, P1, a = 8.164 (2), b =
Jian-Min Zhao et al.
The Journal of organic chemistry, 73(17), 6800-6806 (2008-08-05)
The triptycene-based macrotricyclic host containing two dibenzo-[24]-crown-8 moieties has been found to form stable 1:1 or 1:2 complexes in different complexation modes with different functional paraquat derivatives and secondary ammonium salts in solution and in the solid state. Consequently, the
Xiaofan Ji et al.
Journal of the American Chemical Society, 135(1), 74-77 (2012-12-25)
A supramolecular cross-linked network was fabricated and demonstrated to act as a multiple fluorescent sensor. It was constructed from a fluorescent conjugated polymer and a bisammonium salt cross-linker driven by dibenzo[24]crown-8/secondary ammonium salt host-guest interactions. Compared with the conjugated polymer

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