123447
3,4-Dihydroxy-3-cyclobutene-1,2-dione
≥99.0% (HPLC)
Synonym(s):
Squaric acid
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About This Item
Linear Formula:
(HO)2C4(=O)2
CAS Number:
Molecular Weight:
114.06
Beilstein:
774275
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
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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
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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
Certificates of Analysis (COA)
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Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels
Oswald et al.
Bioconjugate chemistry, 11(3), 438-438 (2000-05-23)
Jian Xie et al.
Organic letters, 6(1), 83-86 (2004-01-03)
[structure: see text] Protein tyrosine phosphatases (PTPases) are important targets in medicinal chemistry. These enzymes play a role in a number of human diseases, including type II diabetes and infection by Yersinia pestis, the causative agent of bubonic plague. Derivatives
Heterocycles, 35, 1149-1149 (1993)
Construction of a 3D array of cadmium (ii) using squarate as a building block.
Maji, Tapas Kumar, et al.
CrystEngComm, 155-158 (2001)
Igor Bensemann et al.
Organic & biomolecular chemistry, 1(8), 1425-1434 (2003-08-22)
The preparation and crystal structures of fourteen complexes of N,N'-bis(2-pyridyl)aryldiamines with dicarboxylic acids and two complexes with squaric acid are reported. The recognition between the carboxylic acids and the 2-aminopyridine units occurs through the formation of the cyclic R(2)2 (8)
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