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123447

Sigma-Aldrich

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

≥99.0% (HPLC)

Sinônimo(s):

Squaric acid

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About This Item

Fórmula linear:
(HO)2C4(=O)2
Número CAS:
2892-51-5
Peso molecular:
114.06
Beilstein:
774275
Número CE:
220-761-4
Número MDL:
MFCD00001334
Código UNSPSC:
12352103
ID de substância PubChem:
24847567
NACRES:
NA.23
Formulário:
solid
Ensaio:
≥99.0% (HPLC)

Nível de qualidade

200

Ensaio

≥99.0% (HPLC)

Formulário

solid

pf

>300 °C (lit.)

cadeia de caracteres SMILES

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

InChI

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

chave InChI

PWEBUXCTKOWPCW-UHFFFAOYSA-N

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Categorias relacionadas

Descrição geral

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.

Aplicação

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.

Pictogramas

Corrosion
GHS05

Palavra indicadora

Danger

Frases de perigo

H314

Classificações de perigo

Eye Dam. 1 - Skin Corr. 1B

Código de classe de armazenamento

8A - Combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

374.0 °F

Ponto de fulgor (°C)

190 °C

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
BCCM1861
BCCL4127
BCCJ3245
BCCH1576
BCCD5797

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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)
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)
Vijayakumar Ramalingam et al.
Organic letters, 10(15), 3315-3318 (2008-07-02)
Environment-sensitive binding of anions to synthetic receptors is important for the functional mimicry of ion channels. We describe new squaramide-based chloride ion receptors whose anion binding cavity can be opened and closed by using carbonyl groups as valves. In nonpolar
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