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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)
Abdalla A Elbashir et al.
Journal of chromatography. A, 1218(31), 5344-5351 (2011-07-06)
Using capillary electrophoresis (CE) three chiral primary amine compounds 1-aminoindan (AI), 1-(1-naphthyl)ethylamine (NEA) and 1,2,3,4-tetrahydro-1-naphthylamine (THAN), exhibited only partial or no separation when β-cyclodextrin (βCD) was used as chiral selector. The use of 18-crown-6 (18C6) as a second additive with
Pradeep R Varadwaj et al.
The journal of physical chemistry. A, 115(45), 13180-13190 (2011-10-04)
Density functional theory calculations, together with quantum theory of atoms in molecules (QTAIM) analyses, have been performed to investigate 18-azacrown-6 complexes of the high-spin late first transition series divalent metal ions in the gas phase and, in some cases, in
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