CAS: 53159-92-5
SKU: S1324
1,2,3,4-Cyclobutanetetracarboxylic Acid | SKU: S1324
synonyms: Cyclobutane-1,2,3,4-tetracarboxylic acid; CBTA; 1,2,3,4-Cyclobutanetetracarboxylic acid; 1,2,3,4-Tetracarboxycyclobutane
1,2,3,4-Cyclobutanetetracarboxylic acid (CBTA, cyclobutane-1,2,3,4-tetracarboxylic acid, C4H4(CO2H)4; C8H8O8) is a cyclobutane ring carrying a carboxylic acid group on each carbon. It has a molecular weight of 232.14 g/mol and is supplied as a white to pale yellow crystalline powder that melts with decomposition at about 242 °C and dissolves in methanol (about 10 mg/mL). The assay is 98%. The tetra-acid is the hydrolysed form and the immediate precursor of 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA), an alicyclic dianhydride that is one of the key monomers for colourless, highly transparent polyimides. CBDA is made by the UV [2+2] photodimerisation of maleic anhydride, and the tetra-acid is dehydrated to the dianhydride with acetic anhydride at elevated temperature. Polyimides derived from CBDA show no absorption tail above about 375 nm in published studies, which is why they are used for flexible display substrates, transparent flexible circuit boards and liquid-crystal alignment layers. Outside polymer chemistry, the tetra-acid forms a cobalt(II) complex under hydrothermal conditions and has been employed as a capping ligand in the preparation of gold colloids. Sarchem Labs offers 1,2,3,4-cyclobutanetetracarboxylic acid (SKU S1324) for polymer, materials and coordination-chemistry customers. Each lot ships with a Certificate of Analysis and Safety Data Sheet, and laboratory to bulk quantities can be quoted on request.

Specifications

Melting Point242°C (dec.) (lit.)
ColorWhite-Yellow
Linear FormulaC4H4(CO2H)4
Formula Weight232.14
Physical FormCrystal-Powder at 20°C
Chemical Name or MaterialCyclobutane-1,2,3,4-tetracarboxylic acid
Molecular Weight232.14 g/mol
SMILES StringOC(=O)C1C(C(C1C(O)=O)C(O)=O)C(O)=O
Assay98%
SolubilityMethanol: soluble 10 mg/mL, clear, colourless to light yellow
CAS Number53159-92-5
Empirical FormulaC8H8O8
NACRESNA.22
PubChem Substance ID24859481
UNSPSC Code12352100
MDL NumberMFCD00013270
InChI1S/C8H8O8/c9-5(10)1-2(6(11)12)4(8(15)16)3(1)7(13)14/h1-4H,(H,9,10)(H,11,12)(H,13,14)(H,15,16)
InChI KeyCURBACXRQKTCKZ-UHFFFAOYSA-N
PubChem CID266034
Quality Level100
Functional GroupsCarboxylic acid (four)
FormSolid (white to pale yellow crystal-powder)

Applications

No Application Found
Colourless polyimide research: the acid is the starting point for polyimide films with high visible-light transparency for flexible displays and flexible circuit substrates, and for liquid-crystal alignment layers.
Coordination polymers and complexes: a tetratopic carboxylate ligand; it forms a cobalt(II) complex under hydrothermal conditions whose crystal structure has been studied by synchrotron and neutron powder diffraction.
Nanoparticle capping: employed as a capping ligand in the preparation of gold colloids.
Cross-linking and polyester chemistry: as a polyfunctional carboxylic acid it can serve as a cross-linker for polyol substrates and as a branching monomer for polyesters.

Product Description

What is 1,2,3,4-Cyclobutanetetracarboxylic Acid?

CBTA is a four-membered carbocycle with a carboxyl group on every ring carbon. The formula is C8H8O8 and the molecular weight is 232.14 g/mol. The ring is strained and rigid, which is why polymers made from it are stiff and, because it is saturated, colourless: there is no extended π-conjugation to absorb visible light. The ring carbons are stereocentres, and several stereoisomers exist (all-cis, cis–trans–cis and others); the CAS number 53159-92-5 is listed without a stereodescriptor, and the isomer present influences the dianhydride route and the polymer properties.

Uses of 1,2,3,4-Cyclobutanetetracarboxylic Acid

Polymer chemists buy the acid, or its dianhydride, as the alicyclic counterpart of aromatic dianhydrides such as pyromellitic dianhydride: polyimides from CBDA are transparent where aromatic polyimides are yellow to brown. Materials chemists also use the tetra-acid as a rigid multidentate ligand for coordination polymers and as a capping agent for metal nanoparticles.

Buying and Handling Considerations

The grade offered is 98% assay. Ask for the Certificate of Analysis of the lot, and tell us the stereoisomer composition and water content you need if the acid will be converted to the dianhydride, because these influence the ring-closure and the polymer colour. Store in a tightly closed container in a cool, dry place. The powder is an irritant: use gloves, eye protection and a dust mask. The dianhydride (CBDA) is a separate product with a different CAS number.

Safety Information

  • Pictogram / Signal Word: GHS07 (exclamation mark) | Warning
  • Hazard Statements: H315 (causes skin irritation), H319 (causes serious eye irritation), H335 (may cause respiratory irritation)
  • Hazard Classification: Eye Irrit. 2, Skin Irrit. 2, STOT SE 3 (target organ: respiratory system)
  • Precautionary Statements: P261, P264, P271, P280, P302 + P352, P305 + P351 + P338
  • Storage Class: 11 – Combustible solids | WGK: 3 | Flash Point: not applicable
  • PPE: Type N95 (US) dust mask, eyeshields, gloves

Avoid breathing dust, use in a ventilated area or fume hood, and wash hands thoroughly after handling.

Related Products

FAQs: 1,2,3,4-Cyclobutanetetracarboxylic Acid

It is used as the precursor of CBDA dianhydride for colourless polyimides, as a tetratopic ligand for coordination complexes and as a capping ligand for gold colloids.

CBTA is the tetra-carboxylic acid (CAS 53159-92-5). CBDA is its dianhydride, formed by dehydration with acetic anhydride, and is the actual monomer used in polyimide synthesis.

The formula is C8H8O8, the molecular weight is 232.14 g/mol and it melts with decomposition at about 242 °C. The assay is 98%.

Because the alicyclic cyclobutane unit has no extended π-conjugation, there is no charge-transfer absorption in the visible region, unlike aromatic dianhydrides such as pyromellitic dianhydride.

It irritates the skin, eyes and respiratory tract (H315, H319, H335), with the signal word Warning. Use gloves, eye protection and a dust mask.

Keep it tightly closed in a cool, dry place at room temperature.

Yes. For SKU S1324, a Certificate of Analysis and Safety Data Sheet come with each lot, and quotations cover laboratory through bulk quantities.