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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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About This Item

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

form

liquid

concentration

1.0 M in THF

density

0.944 g/mL

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 and allylation of functionalized aldehydes.
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.

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Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-2.0 °F

Flash Point(C)

-18.88 °C

Certificates of Analysis (COA)

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Synthesis, 3275-3275 (2006)
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)
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)
Shih-Wey Yeh et al.
Inorganic chemistry, 51(7), 4076-4087 (2012-03-13)
The reversible redox transformations [(NO)(2)Fe(S(t)Bu)(2)](-) ⇌ [Fe(μ-S(t)Bu)(NO)(2)](2)(2-) ⇌ [Fe(μ-S(t)Bu)(NO)(2)](2)(-) ⇌ [Fe(μ-S(t)Bu)(NO)(2)](2) and [cation][(NO)(2)Fe(SEt)(2)] ⇌ [cation](2)[(NO)(2)Fe(SEt)(2)] (cation = K(+)-18-crown-6 ether) are demonstrated. The countercation of the {Fe(NO)(2)}(9) dinitrosyliron complexes (DNICs) functions to control the formation of the {Fe(NO)(2)}(10){Fe(NO)(2)}(10) dianionic reduced Roussin's
Hiroaki Kotani et al.
Journal of the American Chemical Society, 133(29), 11092-11095 (2011-06-28)
Addition of potassium superoxide with 18-crown-6 ether (KO(2)(•-)-18-crown-6) to a toluene solution of an acridinium ion-linked porphyrin triad (Acr(+)-H(2)P-Acr(+)) resulted in a remarkable enhancement of the fluorescence intensity. Thus, Acr(+)-H(2)P-Acr(+) acts as an efficient fluorescence sensor for superoxide. Electron transfer
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