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Sigma-Aldrich

3,4-Dihydroxy-3-cyclobuten-1,2-dion

≥99.0% (HPLC)

Synonym(e):

‘Quadratsäure’

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€ 192,00
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€ 693,00

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5 G
€ 61,80
25 G
€ 192,00
100 G
€ 693,00

About This Item

Lineare Formel:
(HO)2C4(=O)2
CAS-Nummer:
Molekulargewicht:
114.06
Beilstein:
774275
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.23

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Qualitätsniveau

Assay

≥99.0% (HPLC)

Form

solid

mp (Schmelzpunkt)

>300 °C (lit.)

SMILES String

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

InChI

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

InChIKey

PWEBUXCTKOWPCW-UHFFFAOYSA-N

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Allgemeine Beschreibung

Used to synthesize photoconducting squaraines[1] and squarylium dyes.[2]

Anwendung

3,4-Dihydroxy-3-cyclobutene-1,2-dione can be used:
  • In fluorescence detection in immunoassays, hybridization assays, enzymatic reactions, and other analytical procedures.[3]
  • To form diffraction quality crystals.[4]
  • 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.[5]

Piktogramme

Corrosion

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Eye Dam. 1 - Skin Corr. 1B

Lagerklassenschlüssel

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flammpunkt (°F)

374.0 °F

Flammpunkt (°C)

190 °C

Persönliche Schutzausrüstung

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


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

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

Artikel

Professor Chen (Nankai University, China) and his team explain the strategies behind their recent record-breaking organic solar cells, reaching a power conversion efficiency of 17.3%.

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

      Helpful?

  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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