123447

3,4-Dihydroxy-3-cyclobutene-1,2-dione

≥99.0% (HPLC)

• Synonym(s): Squaric acid
• Linear Formula: (HO)₂C₄(=O)₂
• CAS Number: 2892-51-5
• Molecular Weight: 114.06
• Beilstein: 774275
• EC Number: 220-761-4
• MDL number: MFCD00001334
• UNSPSC Code: 12352103
• PubChem Substance ID: 24847567
• NACRES: NA.23

Properties

• Assay: ≥99.0% (HPLC)
• form: solid
• mp: >300 °C (lit.)
• SMILES string: OC1=C(O)C(=O)C1=O
• InChI: 1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
• InChI key: PWEBUXCTKOWPCW-UHFFFAOYSA-N

Description

General description

3,4-dihydroxy-3-cyclobutene-1,2 dione, commonly known as squaric acid, is widely used in bioorganic and medicinal chemistry. It is an inhibitor of glyoxylase, semiqauric acid, pyruvate dehrogenase, and transketolase. It is used as a replacement for phosphate in a peptide-based ligand for an SH₂ domain. Its derivatives are high-affinity ligands for excitatory amino acid receptors. These derivatives are also used as dyes for fluorescence detection of small biological molecules.

Application

3,4-Dihydroxy-3-cyclobutene-1,2-dione can be used:

• In fluorescence detection in immunoassays, hybridization assays, enzymatic reactions, and other analytical procedures.
• To form diffraction quality crystals.
• To synthesize a squarate dianion, which is used as a building block to create uncharged polymeric networks. These ordered structures are used in catalysis, nonlinear optics, electrical conductivity, molecular recognition, and molecular sieves.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 374.0 °F
• Flash Point(C): 190 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves