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
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
EC Number:
220-761-4
Beilstein/REAXYS Number:
774275
MDL number:
Assay:
≥99.0% (HPLC)
Form:
solid
Quality Level
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
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
374.0 °F
flash_point_c
190 °C
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Articles
Professor Chen (Nankai University, China) and his team explain the strategies behind their recent record-breaking organic solar cells, reaching a power conversion efficiency of 17.3%.
Heterocycles, 35, 1149-1149 (1993)
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
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 123447-100G | 04061833595046 |
| 123447-5G | 04061838722317 |
| 123447-25G | 04061838722300 |