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123447

Sigma-Aldrich

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

≥99.0% (HPLC)

Synonyme(s) :

Squaric acid

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5 G
94,20 $
25 G
290,00 $
100 G
1 060,00 $

About This Item

Formule linéaire :
(HO)2C4(=O)2
Numéro CAS:
2892-51-5
Poids moléculaire :
114.06
Beilstein:
774275
Numéro CE :
220-761-4
Numéro MDL:
MFCD00001334
Code UNSPSC :
12352103
ID de substance PubChem :
24847567
Nomenclature NACRES :
NA.23

94,20 $

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Essai

≥99.0% (HPLC)

Forme

solid

Pf

>300 °C (lit.)

Chaîne SMILES 

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

InChI

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

Clé InChI

PWEBUXCTKOWPCW-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.[1] These derivatives are also used as dyes for fluorescence detection of small biological molecules.[2]

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.[2]
  • To form diffraction quality crystals.[3]
  • 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.[4]

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Eye Dam. 1 - Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

374.0 °F

Point d'éclair (°C)

190 °C

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
BCCM1861
BCCL4127
BCCJ3245
BCCH1576
BCCD5797

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
Heterocycles, 35, 1149-1149 (1993)
Construction of a 3D array of cadmium (ii) using squarate as a building block.
Maji, Tapas Kumar, et al.
CrystEngComm, 155-158 (2001)
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)
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is a good way to derivatize squaric acid

    1 answer

    1. The derivatization of squaric acid has not been investigated. It would be up to the end-user to research this application. It may be helpful to review the following publication:
      https://pubs.acs.org/doi/10.1021/ja00959a040

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