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
123447
3,4-Dihydroxy-3-cyclobutene-1,2-dione
≥99.0% (HPLC)
Synonym(s):
Squaric acid
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5 G
$111.00
25 G
$345.00
100 G
$1,250.00
About This Item
Linear Formula:
(HO)2C4(=O)2
CAS Number:
Molecular Weight:
114.06
Beilstein:
774275
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
form:
solid
Assay:
≥99.0% (HPLC)
Recommended Products
Quality Level
Assay
≥99.0% (HPLC)
form
solid
mp
>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
InChI key
PWEBUXCTKOWPCW-UHFFFAOYSA-N
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General 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.[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]
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
374.0 °F
Flash Point(C)
190 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Jian Xie et al.
Organic letters, 6(1), 83-86 (2004-01-03)
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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)
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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