Bicyclo(2.2.2)oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride (COeDA)

CAS Number 1719-83-1

Chemistry Building Blocks, COF Ligands, Diamines and Dianhydrides, Heterocyclic Building Blocks, MOF Ligands, Monomers, Porous Organic Frameworks

MSDS

Bicyclo(2.2.2)oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride (COeDA) CAS 1719-83-1

A dianhydride with a bicyclooctene core

Mainly used as an intermediate for the preparation of imides and MOFs in application of molecular scaffolds, carbon fixation, and supramolecular architectures

Overview
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Bicyclo(2.2.2)oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride (COeDA, CAS number 1719-83-1) has a bicyclooctene fused with two succinic anhydrides. The rigidity of Bicyclo(2.2.2)oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride enables it to be a robust molecular scaffold for derivatization. COeDA can be derivatised by amines for succinimides while the octene favours electrophilic substitution and olefin metathesis. An inhibitor made from COeDA has shown effectiveness (half maximal inhibitory concentration IC₅₀ = 102.2 µM) against SAR-CoV-2 main protease in the inhibition assays. The succinimide derivatives have shown blue/violet fluorescent under UV radiation, hence they can be applied in bioimaging to monitor their bioactivity.

COeDA is used to synthesize metal organic cages (MOCs) ligands. The lantern-type MOCs have record high surface area up to 521 m²/g. Those metal organic complexes can catalyse reaction of CO₂ and epoxides for the purpose of carbon fixation.

For multi-functional materials

High surface area, carbon fixation and fluorescent dye

Carboxylic acid dianhydride building block

For the synthesis of MOF and polyimides

Worldwide shipping

Quick and reliable shipping

High purity

>99% High purity

General Information

CAS Number	1719-83-1
Chemical Formula	C₁₂H₈O₆
Full Name	Bicyclo(2.2.2)oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride
Molecular Weight	249.19 g/mol
Synonyms	4,10-Dioxatetracyclo[5.5.2.02,6.08,12]tetradec-13-ene-3,5,9,11-tetrone
Classification / Family	Dianhydride building block, Polyimides, Molecular scaffolds, MOFs

Chemical Structure

Product Details

Purity	>99%
Melting Point	T_m = 382 °C
Appearance	White to pale yellow powder/crystal

MSDS Documentation

Bicyclo(2.2.2)oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride (COeDA) MSDS Sheet

Literature and Reviews

Design, synthesis and evaluation of fused bicyclo[2.2.2]octene as a potential core scaffold for the non-covalent inhibitors of SARS-CoV-2 3CL^pro main protease, B. Herlah et al., Pharmaceuticals, 15, 539(2022); DOI: 10.3390/ph15050539.
Porous metal-organic cages based on rigid bicyclo[2.2.2]oct-7-ene type ligands: synthesis, structure, and gas uptake properties, B. Suso et al., Chem. Eur. J., e202300732(2023); DOI: 10.1002/chem.202300732.
Structural design of Mn-metal-organic frameworks toward highly efficient solvent-free cycloaddition of CO₂, H. Li et al., Cryst. Growth Des., 21(7), 3728–3735(2021); DOI: 10.1021/acs.cgd.1c00037.
Synthesis, characterization, and crystal structures of imides condensed with p-phenylamino(phenyl) amine and fluorescence property, J. Zhang et al., Materials, 12, 1873(2019); DOI: 10.3390/ma12111873.
Two unexpected temperature-induced supermolecular isomers from multi-topic carboxylic acid: hydrogen bonding layer or helix tube, C. Li et al., Molecules,26, 6938(2021); DOI: 10.3390/molecules26226938.