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194905

Sigma-Aldrich

12-Crown-4

98%

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Synonym(s):
1,4,7,10-Tetraoxacyclododecane
Empirical Formula (Hill Notation):
C8H16O4
CAS Number:
Molecular Weight:
176.21
Beilstein/REAXYS Number:
1363064
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

liquid

refractive index

n20/D 1.463 (lit.)

bp

61-70 °C/0.5 mmHg (lit.)

mp

16 °C (lit.)

density

1.089 g/mL at 25 °C (lit.)

SMILES string

C1COCCOCCOCCO1

InChI

1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2

InChI key

XQQZRZQVBFHBHL-UHFFFAOYSA-N

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1 of 4

This Item
188832274984382655
12-Crown-4 98%

194905

12-Crown-4

15-Crown-5 98%

188832

15-Crown-5

18-Crown-6 ≥99.0%

274984

18-Crown-6

2-Hydroxymethyl-12-crown-4 95%

382655

2-Hydroxymethyl-12-crown-4

Quality Level

100

Quality Level

-

Quality Level

200

Quality Level

-

refractive index

n20/D 1.463 (lit.)

refractive index

n20/D 1.465 (lit.)

refractive index

-

refractive index

n20/D 1.480 (lit.)

form

liquid

form

liquid

form

solid

form

liquid

bp

61-70 °C/0.5 mmHg (lit.)

bp

93-96 °C/0.05 mmHg (lit.)

bp

-

bp

115 °C/0.04 mmHg (lit.)

mp

16 °C (lit.)

mp

-

mp

42-45 °C (lit.)

mp

-

General description

12-Crown-4 is a crown ether generally used as a ligand in coordination chemistry. It is also known as lithium ionophore because of its strong chelating property specific to lithium cation.

Application

12-Crown-4 can be used as:
  • A promoter in the synthesis of poly(diethylsiloxane) (PDES) from monomer hexaethylcyclotrisiloxane using NaOH as a catalyst via anionic ring-opening polymerization.
  • As an additive in the preparation of triarylmethane derivatives by palladium-catalyzed cross coupling reaction of aryl bromides with diarylmethane derivatives.
  • A phase transfer catalyst in organic synthesis.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 1 Inhalation

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Free inorganic, organic, and organometallic ions by treatment of their lithium salts with 12-crown-4
Power PP, et al.
Accounts of Chemical Research, 21(4), 147-153 (1988)
1, 4, 7, 10-Tetraoxacyclododecane (12-crown-4) as neutral carrier for lithium ion in lithium ion selective electrode
Gadzekpo VPY and Christian GD
Analytical Letters, 16(17-18), 1371-1380 (1983)
Mazhar Ali Abbasi et al.
Sensors (Basel, Switzerland), 12(11), 15424-15437 (2012-12-04)
In this study honeycomb-like NiO nanostructures were grown on nickel foam by a simple hydrothermal growth method. The NiO nanostructures were characterized by field emission electron microscopy (FESEM), high resolution transmission electron microscopy (HRTEM) and X-ray diffraction (XRD) techniques. The
Zehra Edis et al.
Pathogens (Basel, Switzerland), 8(4) (2019-10-30)
Antimicrobial agents containing symmetrical triiodides complexes with halogen bonding may release free iodine molecules in a controlled manner. This happens due to interactions with the plasma membrane of microorganisms which lead to changes in the structure of the triiodide anion.
Preparation of poly (diethylsiloxane) with the NaOH/12-crown-4 catalyst
Hedden RC and Cohen C
Polymer, 41(18), 6975-6979 (2000)

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