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Sigma-Aldrich

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

≥99.0% (HPLC)

Sinonimo/i:

Squaric acid

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About This Item

Formula condensata:
(HO)2C4(=O)2
Numero CAS:
2892-51-5
Peso molecolare:
114.06
Beilstein:
774275
Numero CE:
220-761-4
Numero MDL:
MFCD00001334
Codice UNSPSC:
12352103
ID PubChem:
24847567
NACRES:
NA.23

Livello qualitativo

200

Saggio

≥99.0% (HPLC)

Forma fisica

solid

Punto di fusione

>300 °C (lit.)

Stringa SMILE

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

InChI

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

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Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Eye Dam. 1 - Skin Corr. 1B

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

374.0 °F

Punto d’infiammabilità (°C)

190 °C

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCCD5797
BCCD1005
BCCB3244
BCBZ5299
BCBT8429

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Tetrahedron Letters, 48, 3595-3595 (2007)
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)
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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