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194905

Sigma-Aldrich

12-Crown-4

98%

Synonym(s):

1,4,7,10-Tetraoxacyclododecane

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About This Item

Empirical Formula (Hill Notation):
C8H16O4
CAS Number:
294-93-9
Molecular Weight:
176.21
Beilstein:
1363064
EC Number:
206-036-5
MDL number:
MFCD00005103
UNSPSC Code:
12352005
PubChem Substance ID:
24851661
NACRES:
NA.22

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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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
GHS06

Signal Word

Danger

Hazard Statements

H330

Hazard Classifications

Acute Tox. 1 Inhalation

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Changna Yin et al.
Rapid communications in mass spectrometry : RCM, 34(9), e8719-e8719 (2020-01-04)
The poly(ethylene oxide) (PEO)-alkali metal cation interaction is widely used in many areas. The conformation of the PEO-alkali metal cation complex has been studied extensively, but the conformational mechanism is still unclear. Simulations have been used to explain the mechanism
Márkó Grabarics et al.
The Analyst, 145(19), 6313-6333 (2020-07-28)
In the past decade, ion mobility spectrometry (IMS) in combination with mass spectrometry (IM-MS) became a widely employed technique for the separation and structural characterization of ionic species in the gas phase. Similarly to chromatography, where studies on the mechanism
Multilayered ion-imprinted membranes with high selectivity towards Li+ based on the synergistic effect of 12-crown-4 and polyether sulfone
Lu J, et al.
Applied Surface Science, 427, 931-941 (2018)
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)
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