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253197

Sigma-Aldrich

Dibenzo-24-crown-8

98%

Synonym(s):

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

Empirical Formula (Hill Notation):
C24H32O8
CAS Number:
14174-09-5
Molecular Weight:
448.51
Beilstein:
1693744
EC Number:
238-027-7
MDL number:
MFCD00005101
UNSPSC Code:
12352005
PubChem Substance ID:
24855301
NACRES:
NA.22

Assay

98%

mp

103-105 °C (lit.)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
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 =
Travis B Gasa et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(1), 106-116 (2008-12-17)
Paraquat bis(hexafluorophosphate) undergoes stepwise dissociation in acetone. All three species-the neutral molecule, and the mono- and dications-are represented significantly under the experimental conditions typically used in host-guest binding studies. Paraquat forms at least four host-guest complexes with dibenzo[24]crown-8. They are
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