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123447

Sigma-Aldrich

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:
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

Quality Level

200

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM1861
BCCL4127
BCCJ3245
BCCH1576
BCCD5797

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Heterocycles, 35, 1149-1149 (1993)
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)
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)
Carsten Dingels et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(52), 16828-16835 (2012-11-09)
The covalent attachment of poly(ethylene glycol) (PEG) to therapeutically active proteins (PEGylation) has become an important method to deal with the pharmacological difficulties of these polypeptides, such as short body-residence times and immunogenicity. However, the derivatives of PEG used for
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