3A,6a-dimethyltetrahydrocyclobuta[1,2-c:3,4-c']difuran-1,3,4,6-tetraone
[CAS# 137820-87-2]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 3A,6a-dimethyltetrahydrocyclobuta[1,2-c:3,4-c']difuran-1,3,4,6-tetraone
• Synonyms: 1,6-dimethyl-4,9-dioxatricyclo[5.3.0.02,6]decane-3,5,8,10-tetrone
• Molecular Formula: C₁₀H₈O₆
• Molecular Weight: 224.17
• CAS Registry Number: 137820-87-2
• SMILES: CC12C(C(=O)OC1=O)C3(C2C(=O)OC3=O)C

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 456.5±45.0 ºC 760 mmHg (Calc.)^*
• Flash point: 210.3±28.8 ºC (Calc.)^*
• Index of refraction: 1.585 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Discovory and Applicatios

3A,6a-dimethyltetrahydrocyclobuta[1,2-c:3,4-c']difuran-1,3,4,6-tetraone (commonly abbreviated *DMCBDA* and assigned CAS number 137820-87-2) is an organic chemical compound with molecular formula C₁₀H₈O₆. It is one member of a family of saturated bicyclic dianhydrides, in which a cyclobutane core is fused with two tetrahydrofuran-like rings bearing anhydride carbonyl groups. The compound is also systematically described as 1,3-dimethyl-cyclobutane-1,2,3,4-tetracarboxylic dianhydride, reflecting its derivation from a tetracarboxylic acid precursor. Its reported molar mass is 224.17 g mol⁻¹ and it is typically isolated as a crystalline powder with high purity when prepared for research or industrial supply. Commercial suppliers describe standard storage conditions, precautionary hazard classifications, and typical handling as applicable to laboratory chemicals of this class.([Ambeed][1])

The compound’s discovery is rooted in the broader development and cataloging of polyfunctional anhydrides and specialty monomers rather than a single “first synthesis” paper in the academic literature. Dianhydrides of various structures have long been studied and produced for use in polymer chemistry because of their propensity to react with diamines and other nucleophiles to form polyimides and related high-performance polymers. Functionalized cyclic dianhydrides like DMCBDA were developed as part of efforts by chemical manufacturers and materials science researchers to expand the range of monomers available for advanced materials. The detailed original literature reporting the earliest synthesis of this specific dimethyl cyclobutadiol dianhydride is not widely cited in peer-reviewed journals, but its availability from commercial catalogs reflects its acceptance and validation as a synthetic building block.([myuchem.com][2])

The synthesis of compounds in this class typically involves the controlled cyclization and dehydration of appropriate polycarboxylic acid precursors. In the case of Dianhydride monomers, a precursor tetracarboxylic acid such as 1,2,3,4-cyclobutanetetracarboxylic acid is subjected to conditions (often heat and removal of water) that promote intramolecular formation of two anhydride rings. For the dimethyl-substituted analog, appropriate methyl substitution on the cyclobutane ring must be present prior to anhydride formation. While precise academic synthetic procedures for DMCBDA itself are not easily found in open literature, analogous procedures for related dianhydrides are well established and often published in polymer chemistry methodology literature.([ChemicalBook][3])

Applications of 3A,6a-dimethyltetrahydrocyclobuta[1,2-c:3,4-c']difuran-1,3,4,6-tetraone are tied to its role as a reactive intermediate or monomer in specialty chemical processes. Dianhydrides and related polyfunctional anhydrides are cornerstone monomers for the production of polyimides, polyesters, and other high-performance polymers due to their ability to undergo step-growth polymerization with diamines or diols under heat. Such polymers are valued in electronics, aerospace, and materials science for their thermal stability and mechanical properties. Although specific peer-reviewed studies on polymerizations using DMCBDA itself are limited in the open literature, suppliers and materials databases list it among monomers offered for advanced materials research, indicating its use in exploratory polymer synthesis and as a building block for functional materials.([echemi.com][4])

In addition to polymer applications, compounds of this structural class (bicyclic anhydrides) find occasional use as intermediates in organic synthesis where a highly strained bicyclic framework can be transformed into other structures. Reactive anhydride functional groups can be selectively opened or modified to produce diacids, esters, or other derivatives useful in organic synthesis. These transformations are valuable to researchers developing new materials, ligands, or functional small molecules for use in coatings, adhesives, or specialty resins. The documentation from suppliers and chemical inventories demonstrates that DMCBDA is stocked alongside other monomers and intermediates intended for electronics, optical materials, and polymer industries, though detailed academic evaluations of these applications are not yet abundant.([catsyn.com][5])

Because the compound is principally of interest as a specialty monomer or intermediate, it is not widely discussed outside materials science and chemical supply contexts. Its verification in chemical catalogs and its assignment of a CAS registry number confirm its recognized status as a defined chemical substance. Academic literature specifically exploring its discovery and application remains limited, and most detailed protocols for its use are proprietary or contained within industrial process literature rather than open peer-reviewed sources.

References

Hasegawa M, Horie K (2001) Photophysics, photochemistry, and optical properties of polyimides. Progress in Polymer Science 26 2 259–335 DOI: 10.1016/S0079-6700(00)00042-3