Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H2O4 |
| Molecular Weight | 114.0563 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(O)C(=O)C1=O
InChI
InChIKey=PWEBUXCTKOWPCW-UHFFFAOYSA-N
InChI=1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
Squaric acid is a dibasic organic acid and useful intermediate in a variety of synthetic reactions involving the synthesis of photosensitive squarylium dyes and inhibitors of protein tyrosine phosphatases. Medically, squaric acid dibutyl ester or dibutyl squarate derives from a squaric acid is used for the treatment of warts.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis of 3,6-branched oligomannoside fragments of the mannan from Candida albicans cell wall corresponding to the antigenic factor 4. | 2010-07-02 |
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| 2-(Phenylethyl)ammonium hydrogensquarate hemihydrate: crystal structure, solid-state IR-spectroscopic and theoretical characterization. | 2010-06 |
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| Calculations of the relative energies of the 2B1g and 2A2u states of cyclobutanetetraone radical cation and radical anion provide further evidence of a 3B2u ground state for the neutral molecule: a proposed experimental test of the prediction of a triplet ground state for (CO)4. | 2010-01-28 |
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| Multimeric bivalent immunogens from recombinant tetanus toxin HC fragment, synthetic hexasaccharides, and a glycopeptide adjuvant. | 2010-01 |
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| Synthesis, conjugation, and immunological evaluation of the serogroup 6 pneumococcal oligosaccharides. | 2009-12-14 |
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| Rare earth metal squarates incorporating ethylene glycol ligand with a three-dimensional framework structure: RE(C(4)O(4))(1.5)(C(2)H(6)O(2)) (RE = Y, La-Nd, Sm-Lu). | 2009-11-28 |
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| L-Leucinamide hydrogensquarate: spectroscopic and structural elucidation. | 2009-10 |
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| 1,10-Phenanthrolinium hydrogensquarate monohydrate--a non-centrosymmetric structure from two non-chiral agents. | 2009-09-01 |
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| Synthesis of novel organic-inorganic hybrid compounds: lanthanide phosphites incorporating a squarate ligand. | 2009-07-20 |
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| A light-emitting mouse to image skin inflammation. | 2009-05-28 |
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| A new scandium metal organic framework built up from octadecasil zeolitic cages as heterogeneous catalyst. | 2009-05-07 |
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| Identification and SAR of squarate inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2). | 2009-05-01 |
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| Self-assembly of hydrogensquarates: crystal structures and properties. | 2009-04-02 |
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| A monoclinic pseudopolymorph of manganese squarate dihydrate, Mn(mu-C(4)O(4))(H(2)O)(2), built from cubic units. | 2009-04 |
|
| Crystal structures and spectroscopic properties of ester amide and diamide of squaric acid with prolinamide. | 2009-04 |
|
| Temperature- and pressure-induced proton transfer in the 1:1 adduct formed between squaric acid and 4,4'-bipyridine. | 2009-03-25 |
|
| Squaramide hydroxamate-based chemidosimeter responding to iron(III) with a fluorescence intensity increase. | 2009-02-02 |
|
| Reductive disproportionation of carbon dioxide to carbonate and squarate products using a mixed-sandwich U(III) complex. | 2009-01-08 |
|
| Synthesis of a heptasaccharide fragment of the mannan from Candida guilliermondii cell wall and its conjugate with BSA. | 2009-01-05 |
|
| Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate. | 2008-11-15 |
|
| Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. | 2008-11-05 |
|
| Synthesis of a 200-member library of squaric acid N-hydroxylamide amides. | 2008-09-15 |
|
| Carbonyl groups as molecular valves to regulate chloride binding to squaramides. | 2008-08-07 |
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| Alkylsquarates as key intermediates for the rapid preparation of original drug-inspired compounds. | 2008-05 |
|
| Successful treatment of recalcitrant warts with topical squaric acid in immunosuppressed child. | 2008-04-24 |
|
| Synthesis, growth and characterization of a new nonlinear optical material: 4-phenylpyridinium hydrogen squarate (4PHS). | 2008-04 |
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| Structural effects on interconversion of oxygen-substituted bisketenes and cyclobutenediones. | 2008-03-07 |
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| Preparation of glycoconjugates by dialkyl squarate chemistry revisited. | 2008-02-04 |
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| Very large difference in electronic communication of dimetal species with heterobiphenylene and heteroanthracene units. | 2008-01-07 |
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| Structural and spectroscopic elucidation of tetrapetide glycyl-(L)-prolyl-glycyl-glycine and its hydrogensquarate. | 2008 |
|
| Preparation of carbohydrate-oligonucleotide conjugates using the squarate spacer. | 2007-12-01 |
|
| Biphenyls as potent vitronectin receptor antagonists. Part 3: Squaric acid amides. | 2007-11-15 |
|
| Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides. | 2007-11-08 |
|
| Spectroscopic, theoretical and structural characterization of hydrogensquarates of L-threonyl-L-serine and L-serine. | 2007-11 |
|
| Complexes of aminosquarate ligands with first-row transition metals and lanthanides: new insights into their hydrolysis. | 2007-06-25 |
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| Immunogens related to the synthetic tetrasaccharide side chain of the Bacillus anthracis exosporium. | 2007-06-15 |
|
| Synthesis and characterization of covalent mimics of phosphatidylinositol-4,5-bisphosphate micelles. | 2007-06 |
|
| Functionalization of oligosaccharide mimetics and multimerization using squaric diester-mediated coupling. | 2007-04-09 |
|
| [Synthesis of oligosaccharide fragments of mannan from Candida albicans cell wall and their BSA conjugates]. | 2007-03-23 |
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| Dual-mode semisquaraine-based sensor for selective detection of Hg2+ in a micellar medium. | 2007-01-04 |
|
| Structural and spectroscopic analysis of hydrogensquarates of glycine-containing tripeptides. | 2006-12-05 |
|
| Molecular structure, infrared spectrum, and photochemistry of squaric acid dimethyl ester in solid argon. | 2006-09-28 |
|
| Exploring alternative Zn-binding groups in the design of HDAC inhibitors: squaric acid, N-hydroxyurea, and oxazoline analogues of SAHA. | 2006-09-15 |
|
| A new series of glycopeptide antibiotics incorporating a squaric acid moiety. Synthesis, structural and antibacterial studies. | 2006-09 |
|
| Reductive cyclotetramerization of CO to squarate by a U(III) complex: the X-ray crystal structure of [(U (eta-C8H6{SiiPr3-1,4}2)(eta-C5Me4H)]2(mu-eta2: eta2-C4O4). | 2006-08-02 |
|
| The design of organic catalysis for epoxidation by hydrogen peroxide. | 2006-07 |
|
| Structural diversity in manganese squarate frameworks using N,N-donor chelating/bridging ligands: syntheses, crystal structures and magnetic properties. | 2006-03-28 |
|
| VF(C4O4)(H2O)2: a new layer type of diaquavanadium(III) fluoride squarate. | 2006-01 |
|
| Squaric acid-based peptidic inhibitors of matrix metalloprotease-1. | 2005-12-23 |
|
| A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety. | 2005-11 |
Patents
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SUB15362MIG
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125692
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220-761-4
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100000077806
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m10167
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DTXSID9049409
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2892-51-5
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SQUARIC ACID
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SUBSTANCE RECORD
