282790

Benzo-15-crown-5

98%

• Synonym(s): 2,3,5,6,8,9,11,12-Octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin, 2,3-Benzo-1,4,7,10,13-pentaoxacyclopentadecane, Benzo15C5, Monobenzo-15-crown-5
• Empirical Formula (Hill Notation): C₁₄H₂₀O₅
• CAS Number: 14098-44-3
• Molecular Weight: 268.31
• Beilstein/REAXYS Number: 1624106
• EC Number: 237-947-6
• MDL number: MFCD00005945
• UNSPSC Code: 12352005
• PubChem Substance ID: 24857070
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 98%
• mp: 78-80 °C (lit.)
• functional group: ether
• SMILES string: C1COCCOc2ccccc2OCCOCCO1
• InChI: 1S/C14H20O5/c1-2-4-14-13(3-1)18-11-9-16-7-5-15-6-8-17-10-12-19-14/h1-4H,5-12H2
• InChI key: FNEPSTUXZLEUCK-UHFFFAOYSA-N

Description

General description

Benzo-15-crown-5 is a macrocyclic compound that belongs to the class of crown ethers. It is used as a ligand in metal-catalyzed reactions to enhance the reactivity and selectivity by coordinating with metal cations. For instance, it has been utilized in certain metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Stille reactions, to improve the efficiency and selectivity of the transformations. Benzo-15-crown is also employed as a phase-transfer catalyst in organic synthesis.

Application

Benzo-15-crown-5 can be used as a reactant in the synthesis of a phenol-based benzo-15-crown-5 ether resin. The resulting resin further used for lithium isotope separation, which relies on the selective absorption of the Li-6 isotope.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)