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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

Quality Level

100

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 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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ6500
MKCP6464
MKCM0848
MKCK5935
MKCH3056

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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
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
Chhanda Mukhopadhyay et al.
Organic & biomolecular chemistry, 10(7), 1434-1439 (2012-01-04)
"Three methylene spacer" bis(benzimidazolium) derivatives act as a new template for threading dibenzo-24-crown-8 into [2]pseudorotaxanes. In this Article we sought to unveil the difference in the extent of threading of various "three methylene spacer" bis-benzimidazolium moieties based on differences in
Frédéric Coutrot et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(21), 5186-5190 (2009-02-21)
Molecular machines boarding now! Molecular machines containing dibenzo[24]crown-8 (DB24C8) and based on an anilinium and a pyridinium amide station have been prepared. The DB24C8 shuttles upon variation of pH and interacts differently with the pyridinium amide station depending on its
Lei Fang et al.
Journal of the American Chemical Society, 131(20), 7126-7134 (2009-05-08)
A versatile synthetic strategy, which was conceived and employed to prepare doubly threaded, bistable [c2]daisy chain compounds, is described. Propargyl and 1-pentenyl groups have been grafted onto the stoppers of [c2]daisy chain molecules obtained using a template-directed synthetic protocol. Such
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