Squaramide

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title: "Squaramide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ketones", "enamines", "cyclobutenes"] topic_path: "general/ketones" source: "https://en.wikipedia.org/wiki/Squaramide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|ImageFile = Squaramide.svg |ImageSize = 144 |IUPACName = 3,4-diaminocyclobut-3-ene-1,2-dione |Section1={{Chembox Identifiers | CASNo = 5231-89-0 | ChemSpiderID = 2061512 | EC_number = 848-257-5 | PubChem = 2781329 | UNII = 3Q8TZB9ESJ | StdInChI=1S/C4H4N2O2/c5-1-2(6)4(8)3(1)7/h5-6H2 | StdInChIKey=WUACDRFRFTWMHE-UHFFFAOYSA-N | SMILES = C1(=C(C(=O)C1=O)N)N |Section2={{Chembox Properties |C=4|H=4|N=2|O=2 |Appearance = white solid |MeltingPtC = 338–340 Squaramide is the organic compound with the formula O2C4(NH2)2. Not an amide in the usual sense, it is a derivative of squaric acid wherein the two OH groups are replaced by NH2 groups. Squaramides refer to a large class of derivatives wherein some of the H's are replaced by organic substituents. Exploiting their rigid planar structures, these compounds are of interest as hydrogen-bond donors in supramolecular chemistry and squaramide catalysis. Squaramides exhibit 10-50x greater affinity for halides than do thioureas.

Squaramide is prepared by ammonolysis of diesters of squaric acid: :O2C4(OEt)2 + 2 NH3 → O2C4(NH2)2 + 2 EtOH N-Substituted squaramides are prepared similarly, using amines in place of ammonia.

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References

References

  1. (2015). "Bifunctional Amine-Squaramides: Powerful Hydrogen-Bonding Organocatalysts for Asymmetric Domino/Cascade Reactions". Adv. Synth. Catal..
  2. (2021). "Squaric acid as a new chemoselective moiety for mass spectrometry-based metabolomics analysis of amines". RSC Chemical Biology.
  3. (2013). "Be squared: expanding the horizon of squaric acid-mediated conjugations". Chemical Society Reviews.
  4. Storer, R. Ian. (2013). "Squaramide".
  5. (2011). "Squaramides: Physical properties, synthesis and applications". Chemical Society Reviews.
  6. Nathalie Busschaert. (2012). "Squaramides as Potent Transmembrane Anion Transporters". Angew. Chem. Int. Ed..

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