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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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25 ML

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About This Item

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

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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

reaction suitability

core: crown ether

greener alternative product characteristics

Catalysis
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Greener Alternative Product

concentration

1.0 M in THF

density

0.944 g/mL

greener alternative category

Aligned

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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.

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

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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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)
Synthesis, 3275-3275 (2006)
Yu Chen et al.
Journal of the American Chemical Society, 134(13), 5863-5875 (2012-03-10)
Absolute 18-crown-6 (18C6) affinities of five amino acids (AAs) are determined using guided ion beam tandem mass spectrometry techniques. The AAs examined in this work include glycine (Gly), alanine (Ala), lysine (Lys), histidine (His), and arginine (Arg). Theoretical electronic structure
Norihisa Hoshino et al.
Inorganic chemistry, 51(23), 12968-12975 (2012-11-22)
Supramolecular assemblies of anilinium (Ani(+)) and fluoroanilinium derivatives (FAni(+)) with [18]crown-6 were introduced into electrically conducting [Ni(dmit)(2)] crystals (dmit(2-) is 2-thioxo-1,3-dithiole-4,5-dithiolate). The crystal structures, electrical conductivities, and magnetic susceptibilities of four new crystals of (Ani(+))([18]crown-6)[Ni(dmit)(2)](3) (1), (o-FAni(+))([18]crown-6)[Ni(dmit)(2)](3) (2), (m-FAni(+))([18]crown-6)[Ni(dmit)(2)](3) (3)
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