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123447 Sigma-Aldrich

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

≥99.0% (HPLC)

Synonym: Squaric acid

  • CAS Number 2892-51-5

  • Linear Formula (HO)2C4(=O)2

  • Molecular Weight 114.06

  •  Beilstein/REAXYS Number 774275

  •  EC Number 220-761-4

  •  MDL number MFCD00001334

  •  PubChem Substance ID 24847567

  •  NACRES NA.23

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Properties

Related Categories Building Blocks, C3 to C6, Carbonyl Compounds, Chemical Synthesis, Ketones,
Quality Level   200
assay   ≥99.0% (HPLC)
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.

Packaging

25, 100 g in poly bottle

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
GU1800000
Flash Point(F) 
374.0 °F
Flash Point(C) 
190 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Progress for High Performance Tandem Organic Solar Cells

The Centre of Nanoscale Science and Technology and Key Laboratory of Functional Polymer Materials, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China State...
Keywords: Absorption, Nucleic acid annealing, Polymer science, Recombination, Renewable energy, Semiconductor, Separation, Solar cells

Peer-Reviewed Papers
15

References

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