194905

12-Crown-4

98%

• Synonym(s): 1,4,7,10-Tetraoxacyclododecane
• 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

Properties

• 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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H330
• Precautionary Statements: P260 - P271 - P284 - P304 + P340 + P310 - P403 + P233 - P405
• 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