Cyclobutane-1,2,3,4-tetracarboxylic dianhydride
[CAS# 4415-87-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: Cyclobutane-1,2,3,4-tetracarboxylic dianhydride
• Synonyms: 4,9-dioxatricyclo[5.3.0.02,6]decane-3,5,8,10-tetrone
• Molecular Formula: C₈H₄O₆
• Molecular Weight: 196.11
• CAS Registry Number: 4415-87-6
• EC Number: 224-577-5
• SMILES: C12C(C3C1C(=O)OC3=O)C(=O)OC2=O

Properties

• Density: 1.8±0.1 g/cm³ Calc.^*
• Melting point: >300 °C (Expl.)
• Boiling point: 545.3±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 253.7±30.2 °C (Calc.)^*
• Index of refraction: 1.599 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Cyclobutane-1,2,3,4-tetracarboxylic dianhydride is an aromatic-like tetracarboxylic dianhydride with the molecular formula C₈O₆. Structurally, it consists of a cyclobutane ring substituted at all four carbon atoms with carboxylic acid groups that are cyclized to form two anhydride functionalities across opposite carbon pairs. The rigid four-membered ring and the electron-withdrawing anhydride groups confer high reactivity toward nucleophiles and strong thermal stability. The compound typically appears as a pale yellow solid with low solubility in water but good solubility in polar aprotic organic solvents such as N-methylpyrrolidone, dimethylformamide, or acetone.

The primary application of cyclobutane-1,2,3,4-tetracarboxylic dianhydride is as a monomer in the synthesis of polyimides and other high-performance polymers. Its dianhydride groups react with diamines through condensation to form polyimide chains, resulting in polymers with excellent thermal stability, mechanical strength, and chemical resistance. These materials are widely used in electronics, aerospace, coatings, and membranes due to their high-performance characteristics.

The compound is also employed as a crosslinking agent and in the preparation of functionalized cyclobutane derivatives. The high reactivity of the anhydride groups allows for selective acylation, esterification, or amide formation with alcohols and amines, providing versatile intermediates for advanced organic synthesis.

Cyclobutane-1,2,3,4-tetracarboxylic dianhydride can be prepared by oxidation of cyclobutane-1,2,3,4-tetracarboxylic acid, typically using dehydrating agents or thermal treatment to induce anhydride formation. Handling requires care due to its reactivity with nucleophiles and potential to hydrolyze in the presence of moisture, producing the corresponding tetraacid.

Overall, cyclobutane-1,2,3,4-tetracarboxylic dianhydride is a valuable tetrafunctional building block in polymer chemistry and organic synthesis. Its combination of a rigid cyclobutane core and highly reactive anhydride groups enables the construction of high-performance polymers, crosslinked networks, and functionalized derivatives for demanding industrial and research applications.

References

2025. A GSH-consuming polymeric nanoparticles drives ferroptosis amplification and combines chemotherapy to amplify breast cancer treatment. Journal of Nanobiotechnology, 23(1).
DOI: 10.1186/s12951-025-03569-7

2024. Preparation and properties of semi-alicyclic thermoplastic polyimide sheets from stereoisomeric hydrogenated pyromellitic dianhydrides and fluorinated diamine. Journal of Polymer Research, 31(3).
DOI: 10.1007/s10965-024-03934-4