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901591

Sigma-Aldrich

18-Crown-6 solution

1.0 M in THF

Synonym(s):

1,4,7,10,13,16-Hexaoxacyclooctadecane

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25 ML
$403.75

About This Item

Linear Formula:
C12H24O6
CAS Number:
17455-13-9
MDL number:
MFCD00005113
UNSPSC Code:
12352005
NACRES:
NA.22

$403.75

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Available to ship onMay 05, 2025Details

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form

liquid

concentration

1.0 M in THF

density

0.944 g/mL

SMILES string

O1CCOCCOCCOCCOCCOCC1

InChI

1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2

InChI key

XEZNGIUYQVAUSS-UHFFFAOYSA-N

Application

18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds[1] and allylation of functionalized aldehydes.[2]
Additive for greener etherification using KF-alumina.
Additive for greener etherification using KF-alumina.

Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6
Phase-transfer catalyst used in a chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.[3]

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-2.0 °F

flash_point_c

-18.88 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3465

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Synthesis, 3275-3275 (2006)
Preparation and purification of 18-crown-6 [1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane].
Gokel GW, et al.
The Journal of Organic Chemistry, 39(16), 2445-2446 (1974)
Phase-transfer alkylation of heterocycles in the presence of 18-crown-6 and potassium tert-butoxide.
Guida WC and Mathre DJ
The Journal of Organic Chemistry, 45(16), 3172-3176 (1980)
Yu Chen et al.
Journal of the American Society for Mass Spectrometry, 23(11), 2020-2030 (2012-08-29)
Absolute 18-crown-6 (18C6) binding affinities of four protonated acetylated amino acids (AcAAs) are determined using guided ion beam tandem mass spectrometry techniques. The AcAAs examined in this work include: N-terminal acetylated lysine (N(α)-AcLys), histidine (N(α)-AcHis), and arginine (N(α)-AcArg) as well
Yu Chen et al.
Journal of the American Chemical Society, 134(4), 2313-2324 (2012-01-14)
Absolute 18-crown-6 (18C6) affinities of nine protonated peptidomimetic bases are determined using guided ion beam tandem mass spectrometry techniques. The bases (B) included in this work are mimics for the n-terminal amino group and the side chains of the basic
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