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Merck
CN

901591

18-Crown-6 solution

greener alternative

1.0 M in THF, liquid

Synonym(s):

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

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About This Item

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

Key Documents

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Product Name

18-Crown-6 solution, 1.0 M in THF

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

form

liquid

greener alternative product characteristics

Catalysis
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concentration

1.0 M in THF

density

0.944 g/mL

greener alternative category

Aligned

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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.

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

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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

WGK 3

flash_point_f

-2.0 °F

flash_point_c

-18.88 °C

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3465

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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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