12-Crown-4

• CAT Number: I000192
• CAS Number: 294-93-9
• Molecular Formula: C8H16O4
• Molecular Weight: 176.21
• Purity: ≥95%
• Solubility: Soluble in DMSO
• Storage: Store at 2-8 °C
• IUPAC Name: 1,4,7,10-tetraoxacyclododecane
• InChI: InChI=1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2
• InChIKey: XQQZRZQVBFHBHL-UHFFFAOYSA-N
• SMILES: C1COCCOCCOCCO1

12-Crown-4 (Cat.No: I000192) is an organic compound with the chemical formula C8H16O4. It is a cyclic ether with a crown-shaped structure that contains four oxygen atoms. 12-Crown-4 is commonly used as a ligand in coordination chemistry to coordinate with metal ions, particularly potassium ions. It can also be used as a phase-transfer catalyst in organic synthesis, and as a component in electrolyte solutions for batteries.

Reference

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PubMed PMID: 18965304.11: Masiker MC, Mayne CL, Boone BJ, Orendt AM, Eyring EM. 7Li NMR chemical shift titration and theoretical DFT calculation studies: solvent and anion effects on second-order complexation of 12-crown-4 and 1-aza-12-crown-4 with lithium cation in several aprotic solvents. Magn Reson Chem. 2010 Feb;48(2):94-100. doi: 10.1002/mrc.2542. PubMed PMID: 19950215.12: Gao K, Xu C, Cui Z, Liu C, Gao L, Li C, Wu D, Cai HL, Wu XS. The growth mechanism and ferroelectric domains of diisopropylammonium bromide films synthesized via 12-crown-4 addition at room temperature. Phys Chem Chem Phys. 2016 Mar 21;18(11):7626-31. doi: 10.1039/c6cp00568c. PubMed PMID: 26956668.13: Chu IK, Siu SO, Lam CN, Chan JC, Rodriquez CF. Formation of molecular radical cations of aliphatic tripeptides from their complexes with CuII(12-crown-4). Rapid Commun Mass Spectrom. 2004;18(16):1798-802. PubMed PMID: 15329872.14: Harrington JM, Jones SB, White PH, Hancock RD. Possible role of relativistic effects in the plasticity of the coordination geometry of cadmium(II). A voltammetric study of the stability of the complexes of cadmium(II) with 12-crown-4,15-crown-5 and 18-crown-6 in aqueous solution and the structures of [Cd(benzo-18-crown-6)(NCS)(2)] and [K(18-crown-6)][Cd(SCN)(3)]. Inorg Chem. 2004 Jul 12;43(14):4456-63. PubMed PMID: 15236559.15: Inokuchi Y, Nakatsuma M, Kida M, Ebata T. Conformation of Alkali Metal Ion-Benzo-12-Crown-4 Complexes Investigated by UV Photodissociation and UV-UV Hole-Burning Spectroscopy. J Phys Chem A. 2016 Aug 18;120(32):6394-401. doi: 10.1021/acs.jpca.6b06626. Epub 2016 Aug 4. PubMed PMID: 27459367.16: Habata Y, Yamada S, Osaka F. Crown bowl: metallocyclophane by self-assembly of 4/’-pyridylmethyl-armed 12-crown-4 ethers with Ag+ ions. Inorg Chem. 2006 Feb 6;45(3):987-91. PubMed PMID: 16441104.17: Alizadeh N. 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