Dibenzo-18-crown-6 - ≥98% , CAS No.14187-32-7

CAS: 14187-32-7 Cat. No.: D102033 Molecular Weight: 360.4 Beilstein Registry Number: 1162153 EC Number: 238-041-3

GRADE & PURITY ≥98%

Synonyms

Crown ether dibenzo-18-crown-6 | Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro- | Dibenzo[b,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro- | BRN 1162153 | 6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

Phase-transfer catalyst employed in monoazaporphyrin syntheses. Agent used for ion transfer across membranes and as a synthon for preparation of liquid crystal polyesters

Dibenzo-18-crown-6 is a macrocyclic ligand used in the selective binding and extraction of alkali metal cations in solution phase.

Specifications

Synonyms

Crown ether dibenzo-18-crown-6 | Dibenzo(b, k)(1, 4, 7, 10, 13, 16)hexaoxacyclooctadecin, 6, 7, 9, 10, 17, 18, 20, 21-octahydro- | Dibenzo[b, 4, 7, 10, 13, 16]hexaoxacyclooctadecin, 6, 7, 9, 10, 17, 18, 20, 21-octahydro- | BRN 1162153 | 6, 7, 9, 10, 17, 18, 20, 21-octahydrodibenzo[b, k][

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

This is a phase-transfer catalyst used in monoazaporphyrin syntheses. An agent used for ion transfer across membranes and as a synthon in preparation of liquid crystal polyesters.

Storage

Protected from light, Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488183022
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183022
• Canonical Smiles: C1COC2=CC=CC=C2OCCOCCOC3=CC=CC=C3OCCO1
• IUPAC Name: 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaene
• InChIKey: YSSSPARMOAYJTE-UHFFFAOYSA-N
• INCHI: 1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2
• Isomeric SMILES: C1COC2=CC=CC=C2OCCOCCOC3=CC=CC=C3OCCO1
• WGK Germany: 2
• RTECS: HP5386000
• Molecular Weight: 360.4
• Beilstein: 1162153
• Reaxy-Rn: 1162153
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1162153&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Alkyl aryl ethers
• Alternative Parents: Benzenoids Oxacyclic compounds Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alkyl aryl ether - Benzenoid - Oxacycle - Organoheterocyclic compound - Dialkyl ether - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.
• External Descriptors: crown ether

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MCF7 (126967 Activities)

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MIA PaCa-2 (5949 Activities)

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NCI-H460 (60772 Activities)

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HeLa (62764 Activities)

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Associated Targets(non-human)

Escherichia coli (133304 Activities)

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Bacillus subtilis (32866 Activities)

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Gallus gallus (1187 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in CHCl3: 25 mg/ml.Sparingly soluble in water
• Sensitivity: Moisture sensitive；Light sensitive
• Boil Point(°C): 382°C
• Melt Point(°C): 162-164°C
• Molecular Weight: 360.400 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 360.157 Da
• Monoisotopic Mass: 360.157 Da
• Topological Polar Surface Area: 55.400 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 300.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yu Zhang, Junming Dai, Hua Lai, Yinhua Wan, Young Moo Lee, Yongbing Zhuang.  (2023)  Finely Adjusted Intrinsically Microporous Copolyimide Electrolyte Membranes for Fuel Cells Operating in a Wide Temperature Range.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.3c00395]

2. Sisheng Fang, Hai Tang, Meng Wang, Zhaozan Xu, Nanwen Li.  (2023)  The antifouling and separation performance of an ultrafiltration membrane derived from a novel amphiphilic copolymer containing a crown ether.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2023.121620]

3. Fangling Wu, Xishi Wu, Chaoxian Chi, Chuan-Fan Ding.  (2022)  Simultaneous Differentiation of C═C Position Isomerism in Fatty Acids through Ion Mobility and Theoretical Calculations.  ANALYTICAL CHEMISTRY,      [PMID:36008361] [10.1021/acs.analchem.2c02706]

4. Chenshi Shang, Yingxi Liu, Xiangrui Zeng, Wan Jie Luo, Lulu Wang, Jilin Wang.  (2022)  Preparation and characterization of organic-inorganic hybrid anion exchange membrane based on crown ether functionalized mesoporous SBA-NH2.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2022.02.137]

5. Chenshi Shang, Ze Wang, Lulu Wang, Jilin Wang.  (2020)  Preparation and characterization of a polyvinyl alcohol grafted bis-crown ether anion exchange membrane with high conductivity and strong alkali stability.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2020.04.134]

6. Jicheng Xu, Zhilong Pu, Xuechao Xu, Yuanyuan Wang, Dongya Yang, Tao Zhang, Fengxian Qiu.  (2019)  Simultaneous adsorption of Li(I) and Rb(I) by dual crown ethers modified magnetic ion imprinting polymers.  APPLIED ORGANOMETALLIC CHEMISTRY,  33  (3): (e4778).  [PMID:] [10.1002/aoc.4778]

7. Yao Pan, Shugai Feng, Chaoxian Chi, Fangling Wu, Chuan-Fan Ding.  (2025)  Application of ion mobility mass spectrometry and theoretical calculation in the analysis of sulfonamide antibiotics.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2025.107378]

8. Balaji Panchal, Yuzhuang Sun, Cunliang Zhao, Bangjun Liu, Kai Bian, Jinxi Wang, Qiaojing Zhao.  (2024)  Green fuel production from waste fried sunflower oil using reusable mesoporous COP-KOH catalyst with a kinetic study.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125258]

9. Sheng Chen, Lina Wu, Zhicheng Wu, Zhikun Liu, Zhihua Qiu, Lisheng Chi.  (2024)  Highly efficient removal of Sr2+ from aqueous solutions using a polyacrylic acid/crown-ether/graphene oxide hydrogel composite.  RSC Advances,  14  (11): (7825-7835).  [PMID:38444965] [10.1039/D3RA08789A]

10. Jianing Yan, Shiwen Zhang, Lulu Wang, Fan Zhang, Yang Zhang, Jilin Wang.  (2025)  High-performance Cross-linked Anion Exchange Membranes Based on Rigid Poly(crown ether) and Flexible Quaternary Ammonium Poly(vinyl alcohol) for Fuel Cells.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.142082]

11. Jie Zhang, Meng-Ping Ren, Man Xu, Zhonghui Zhang, Mingxue An, Yang Lu, Xiao-Wu Lei, Zhongliang Gong, Cheng-Yang Yue.  (2024)  Ultrafast Visual Detection of a Trace Amount of Water by Highly Efficient Hybrid Manganese Halides.  ACS Applied Materials & Interfaces,      [PMID:38961579] [10.1021/acsami.4c05411]

12. Runcheng Tan, Guangqi Huang, Cong Wei, Zepeng He, Tianyu Zhao, Yi Shi, Zhijia Liu, Yongming Chen.  (2024)  Influence of structural variations in polysarcosine functionalized lipids on lipid nanoparticle-mediated mRNA delivery.  JOURNAL OF POLYMER SCIENCE,      [PMID:] [10.1002/pol.20240154]

13. Haisong Zhao, Lei Zhang, Hongsen Hui, Hongchang Pei, Xianhui Li.  (2025)  Construction of crown ether-based polyamide composite nanofiltration membrane with high Mg2+ transportation barrier for efficient Mg2+/Li+ separation.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2025.124866]

14. Yike Chen, Wenju Shi, Meitong Liu, Zhihong Huang, Jianshe Hu, Zhangpei Chen.  (2026)  A Crown Ether-Based Covalent Organic Polymer Composite Membrane and Its Application in Molecular Separation.  Membranes,  16  (2): (56).  [PMID:41745498] [10.3390/membranes16020056]

15. Naisheng Wu, Sisi He, Huiqi Ding, Fangling Wu, Yu Xiao, Li Ding, Chuan-Fan Ding.  (2026)  Differentiation of positional isomers of branched-chain fatty acids using ion mobility-mass spectrometry based on host-guest chemistry.  FOOD CHEMISTRY,      [PMID:41762563] [10.1016/j.foodchem.2026.148516]