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158399

Sigma-Aldrich

Dibenzo-18-crown-6

98%

Synonym(s):

2,3,11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene, 6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecene, DB18C6

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About This Item

Empirical Formula (Hill Notation):
C20H24O6
CAS Number:
14187-32-7
Molecular Weight:
360.40
Beilstein:
1162153
EC Number:
238-041-3
MDL number:
MFCD00005098
UNSPSC Code:
12352005
PubChem Substance ID:
24849732
NACRES:
NA.22

Assay

98%

mp

162-164 °C (lit.)

SMILES string

C1COc2ccccc2OCCOCCOc3ccccc3OCCO1

InChI

1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2

InChI key

YSSSPARMOAYJTE-UHFFFAOYSA-N

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General description

Dibenzo-18-crown-6 is a macrocyclic ligand used in the selective binding and extraction of alkali metal cations in solution phase.

Application

Phase-transfer catalyst employed in monoazaporphyrin syntheses. Agent used for ion transfer across membranes and as a synthon for preparation of liquid crystal polyesters.

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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Binding selectivity of dibenzo-18-crown-6 for alkali metal cations in aqueous solution: A density functional theory study using a continuum solvation model
Chang Min C et al.
Chemistry Central Journal, 6, 1-8 (2012)
Tetrahedron Letters, 36, 1567-1567 (1995)
Acta Polym., 45, 308-308 (1994)
Solvent influence upon complex formation between dibenzo-18-crown-6 with the Y3+ metal cation in pure and binary mixed organic solvents
GH Rounaghi et al.
Journal of Chemical and Engineering Data, 56, 2836-2840 (2011)
Ying Han et al.
The Journal of organic chemistry, 77(5), 2422-2430 (2012-02-11)
A new triptycene-derived macrotricyclic host containing two dibenzo-[18]-crown-6 moieties was synthesized and shown to form 1:1 complexes with paraquat derivatives in solution, in which the guests all thread the central cavity of the host. However, it was interestingly found that
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