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282790

Sigma-Aldrich

Benzo-15-crown-5

98%

Synonym(s):

2,3,5,6,8,9,11,12-Octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin, 2,3-Benzo-1,4,7,10,13-pentaoxacyclopentadecane, Benzo15C5, Monobenzo-15-crown-5

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About This Item

Empirical Formula (Hill Notation):
C14H20O5
CAS Number:
14098-44-3
Molecular Weight:
268.31
Beilstein/REAXYS Number:
1624106
EC Number:
237-947-6
MDL number:
MFCD00005945
UNSPSC Code:
12352005
PubChem Substance ID:
24857070
NACRES:
NA.22

assay

98%

mp

78-80 °C (lit.)

functional group

ether

SMILES string

C1COCCOc2ccccc2OCCOCCO1

InChI

1S/C14H20O5/c1-2-4-14-13(3-1)18-11-9-16-7-5-15-6-8-17-10-12-19-14/h1-4H,5-12H2

InChI key

FNEPSTUXZLEUCK-UHFFFAOYSA-N

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General description

Benzo-15-crown-5 is a macrocyclic compound that belongs to the class of crown ethers. It is used as a ligand in metal-catalyzed reactions to enhance the reactivity and selectivity by coordinating with metal cations. For instance, it has been utilized in certain metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Stille reactions, to improve the efficiency and selectivity of the transformations. Benzo-15-crown is also employed as a phase-transfer catalyst in organic synthesis.

Application

Benzo-15-crown-5 can be used as a reactant in the synthesis of a phenol-based benzo-15-crown-5 ether resin. The resulting resin further used for lithium isotope separation, which relies on the selective absorption of the Li-6 isotope.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
U4241
U3044
STBJ6217
STBJ3272
STBJ3161

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J Patrick Shupp et al.
Dalton transactions (Cambridge, England : 2003), 46(28), 9163-9171 (2017-07-05)
We report the synthesis, interconversions and X-ray structures of a set of [mFe-nS]-type carbonyl clusters (where S = S
Li-Jing Du et al.
Food chemistry, 262, 118-128 (2018-05-13)
In this study, dispersive micro solid phase extraction (DMSPE) combined with ultrahigh-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry method was established to extract and determine sudan dyes and their metabolites in real samples. The crown ether microfunctionalized
Shinzo Kagabu et al.
Bioorganic & medicinal chemistry letters, 19(11), 2947-2948 (2009-05-05)
Imidacloprid (IMI) derivatives conjugated with benzo-15-crown-5 and benzo-18-crown-6 structures, applied for the first time to explore novel insecticidal molecule, elicited strong excitatory toxic signs to the house flies and stunningly exhibited three to five times higher insecticidal activity than that

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