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194905 Sigma-Aldrich

12-Crown-4

98%

Synonym: 1,4,7,10-Tetraoxacyclododecane

  • CAS Number 294-93-9

  • Empirical Formula (Hill Notation) C8H16O4

  • Molecular Weight 176.21

  •  Beilstein/REAXYS Number 1363064

  •  EC Number 206-036-5

  •  MDL number MFCD00005103

  •  PubChem Substance ID 24851661

  •  NACRES NA.22

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Properties

Related Categories Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Synthetic Reagents
Quality Level   100
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

Description

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.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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