CAS 2892-51-5 3,4-Dihydroxy-3-cyclobutene-1,2-dione

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

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Catalog Number

ACM2892515-1

Product Name

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

Structure

CAS

2892-51-5

Category

Synthetic Tools and Reagents

Synonyms

Squaric acid

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.

IUPAC Name

3,4-Dihydroxycyclobut-3-ene-1,2-dione

Molecular Weight

114.06

Molecular Formula

(HO)2C4(=O)2

Canonical SMILES

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

InChI

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

InChI Key

PWEBUXCTKOWPCW-UHFFFAOYSA-N

Boiling Point

250.96 °C

Melting Point

>300 °C

Flash Point

190 °C

Purity

95%+

Density

1.82 g/cm³

Solubility

Soluble in water

Appearance

Gray crystalline solid

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.

Storage

Inert atmosphere,Room Temperature

Complexity

178

Covalently-Bonded Unit Count

EC Number

220-761-4

Exact Mass

113.99530854

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Formal Charge

Heavy Atom Count

MDL Number

MFCD00001334

MeSH Entry Terms

squaric acid;squaric acid, dipotassium salt;squaric acid, disilver (+1) salt;squaric acid, disodium salt;squaric acid, monopotassium salt;squaric acid, monopotassium salt monohydrate;squaric acid, nickel (+2), (1:1) salt dihydrate

Monoisotopic Mass

113.99530854

NSC Number

624671;125692

Packaging

Packaging
5 g in glass bottle
25, 100 g in poly bottle

Rotatable Bond Count

Topological Polar Surface Area

74.6 Å²

UNII

SVR9D0VODW

XLogP3