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Merck
CN

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:
2892-51-5
Molecular Weight:
114.06
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
24847567
EC Number:
220-761-4
Beilstein/REAXYS Number:
774275
MDL number:
MFCD00001334

Key Documents

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Product Name

3,4-Dihydroxy-3-cyclobutene-1,2-dione, ≥99.0% (HPLC)

InChI key

PWEBUXCTKOWPCW-UHFFFAOYSA-N

InChI

1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H

SMILES string

OC1=C(O)C(=O)C1=O

assay

≥99.0% (HPLC)

form

solid

mp

>300 °C (lit.)

Quality Level

200

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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.

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3333
BCCM1861
BCCL4127
BCCJ3245
BCCH1576

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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
Tetrahedron Letters, 48, 3595-3595 (2007)
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)
Construction of a 3D array of cadmium (ii) using squarate as a building block.
Maji, Tapas Kumar, et al.
CrystEngComm, 155-158 (2001)
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