123447

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

≥99.0% (HPLC)

• Synonyme(s) : Squaric acid
• Formule linéaire : (HO)₂C₄(=O)₂
• Numéro CAS: 2892-51-5
• Poids moléculaire : 114.06
• Numéro Beilstein : 774275
• Numéro CE : 220-761-4
• Numéro MDL: MFCD00001334
• Code UNSPSC : 12352103
• ID de substance PubChem : 24847567
• Nomenclature NACRES : NA.23

Propriétés

• Pureté: ≥99.0% (HPLC)
• Forme: solid
• Pf: >300 °C (lit.)
• Chaîne SMILES: OC1=C(O)C(=O)C1=O
• InChI: 1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
• Clé InChI: PWEBUXCTKOWPCW-UHFFFAOYSA-N

Description

Description générale

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.

Informations sur la sécurité

• Pictogrammes: GHS05
• Mention d'avertissement: Danger
• Mentions de danger: H314
• Conseils de prudence: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Classification des risques: Eye Dam. 1 - Skin Corr. 1B
• Code de la classe de stockage: 8A - Combustible corrosive hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 374.0 °F
• Point d'éclair (°C): 190 °C
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Faceshields, Gloves