5231-87-8

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl squarate is used as an intermediate for pharmaceutical products, playing a crucial role in the development and synthesis of various medications.
Used in Photochemical Industry:
Diethyl squarate is utilized as a photochemical intermediate, particularly in the dry-view process. It is also involved in the synthesis of photosensitive squaraine dyes, such as laser dyes used in CD-ROM technology.
Used in Synthesis of Furanones and Quinones:
3,4-Dethoxy-3-cyclobutene-1,2-dione, a derivative of diethyl squarate, is used as a starting material for the synthesis of furanones and quinones. It undergoes ethoxy substitution with amines and unsaturated organosilanes, which are essential in the production of these compounds.
Used in Synthesis of Functional Polymers:
Diethyl squarate serves as an intermediate in the synthesis of functional polymers, which have a wide range of applications in various industries due to their unique properties and functionalities.

InChI:InChI=1/C8H10O4/c1-3-11-7-5(9)6(10)8(7)12-4-2/h3-4H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 2892-51-5 squaric acid 
• 3200-96-2 2,3,4,4-tetrachloro-cyclobut-2-en-1-one 
• 122-51-0 orthoformic acid triethyl ester 
• 1007834-24-3 2,3-diethoxy-1,3-butadiene-1,4-dione 
• 61699-62-5 diisopropyl squarate 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 61699-49-8 1,2-di-(2-phenylethyloxy)-cyclobutenedione 
• 131588-95-9 3-Ethoxy-4-<(2-hydroxy-1,1-dimethylethyl)amino>-3-cyclobutene-1,2-dione 
• 22118-95-2 3-ethoxy-4-phenyl-3-cyclobutylene-1,2-dione 
• 158599-29-2 2,3-diethoxy-4-hydroxy-4-phenyl-2-cyclobutenone 
• 102268-44-0 triphenylphosphoranylidenecylobutanetrione 
• 73279-58-0 3-Ethoxy-4-p-tolyl-3-cyclobuten-1,2-dion 
• 5222-73-1 3,4-dimethoxy-3-cyclobutene-1,2-dione 
• 131588-97-1 3-Ethoxy-4-<2-(4-hydroxyphenyl)ethylamino>-3-cyclobutene-1,2-dione 
• 147932-86-3 3-ethoxy-4-phenacylcyclobut-3-ene-1,2-dione 
• 131588-96-0 3-Ethoxy-4-<(1R)-(1-ethyl-2-hydroxyethyl)amino>-3-cyclobutene-1,2-dione 
• 21619-12-5 3-ethoxy-4-(2-oxocyclohexyl)cyclobut-3-ene-1,2-dione 
• 131589-03-2 3-Ethoxy-4-<(1'S,2'R)-(2'-hydroxy-1'-methyl-2'-phenylethyl)(methyl)amino>-3-cyclobutene-1,2-dione 
• 131589-09-8 3,4-Bis<(1'S,2'R)-(2'-hydroxy-1'-methyl-2'-phenylethyl)(methyl)amino>-3-cyclobutene-1,2-dione 
• 131588-98-2 3-Ethoxy-4-<(1S,2S)-(2-hydroxy-1-hydroxymethyl-2-phenylethyl)amino>-3-cyclobutene-1,2-dione 

Relevant academic research and scientific papers

An Unsymmetrical Squaraine-Based Activatable Probe for Imaging Lymphatic Metastasis by Responding to Tumor Hypoxia with MSOT and Aggregation-Enhanced Fluorescent Imaging

Optoacoustic imaging has great potential for preclinical research and clinical practice, and designing robust activatable optoacoustic probes for specific diseases is beneficial for its further development. Herein, an activatable probe has been developed for tumor hypoxia imaging. For this probe, indole and quinoline were linked on each side of an oxocyclobutenolate core to form an unsymmetrical squaraine. A triarylamine group was incorporated to endow the molecule with the aggregation enhanced emission (AEE) properties. In aqueous media, the squaraine chromophore aggregates into the nanoprobe, which specifically responds to nitroreductase and produces strong optoacoustic signals due to its high extinction coefficient, as well as prominent fluorescence emission as a result of its AEE feature. The nanoprobe was used to image tumor metastasis via the lymphatic system both optoacoustically and fluorescently. Moreover, both the fluorescence signals and three-dimensional multispectral optoacoustic tomography signals from the activated nanoprobe allow us to locate the tumor site and to map the metastatic route.

Efficient far red sensitization of nanocrystalline TiO2 films by an unsymmetrical squaraine dye

An asymmetric squaraine sensitizer comprising an anchoring group was engineered at the molecular level and synthesized. The functionalized novel squaraine sensitizers upon anchoring onto a TiO2 film exhibit an unprecedented incident photon to current conversion efficiency of 85%. The photovoltaic data of this sensitizer using an electrolyte having composition of 0.6 M M-methyl-N-butyl imidazolium iodide, 0.05 M iodine, 0.1 M LiI, 0.05 M tert-butylpyridine in a 15/85 (v/v) mixture of valeronitrile and acetonitrile revealed a short circuit photocurrent density of 10.5 ± 0.2 mA/cm2, an open circuit voltage of 603 ± 10 mV, and a fill factor of 0.71 ± 0.02, corresponding to an overall conversion efficiency of 4.50% under standard AM 1.5 sunlight. Copyright

Multiple linker half-squarylium dyes for dye-sensitized solar cells; Are two linkers better than one?

The synthesis and full characterization of new half-squaraine dyes (Hf-SQ) containing two or three carboxylate-based linker units is reported and these dyes tested in dye-sensitized solar cell (DSC) devices. The data show improved device efficiency for a Hf-SQ dye with two linkers (η = 5.5%) compared to the highest efficiency Hf-SQ previously reported which had only a single linker (η = 5.0%); this is mainly due to improved Voc. To understand the effects of using multiple dye linker groups, device I-V data have been correlated with single crystal X-ray structural analysis and dye electrical properties (both in solution and adsorbed to TiO2) using UV-visible and ATR-IR spectroscopy along with cyclic voltammetry, and also theoretical studies using density functional theory (DFT) calculations. These data show that positioning the linkers near the dye LUMO and so that this enables complete linker chemisorption are key factors for device performance.

Cyclic sulfone compound and preparation method, application and pharmaceutical composition thereof

The invention belongs to the technical field of pharmacy, and relates to a cyclic sulfone compound and a preparation method, application and a pharmaceutical composition thereof. The cyclic sulfone compound is shown as a formula (I), is a CXCR2 antagonist

Novel bisubstrate uridine-peptide analogues bearing a pyrophosphate bioisostere as inhibitors of human O-GlcNAc transferase

Protein O-linked β-D-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation), an essential post-translational as well as cotranslational modification, is the attachment of β-D-N-acetylglucosamine to serine and threonine residues of nucleocytoplasmic proteins. An aberrant O-GlcNAc profile on certain proteins has been implicated in metabolic diseases such as diabetes and cancer. Inhibitors of O-GlcNAc transferase (OGT) are valuable tools to study the cell biology of protein O-GlcNAc modification. In this study we report novel uridine-peptide conjugate molecules composed of an acceptor peptide covalently linked to a catalytically inactive donor substrate analogue that bears a pyrophosphate bioisostere and explore their inhibitory activities against OGT by a radioactive hOGT assay. Further, we investigate the structural basis of their activities via molecular modelling, explaining their lack of potency towards OGT inhibition.

The Impact of Chiral Citronellyl-Functionalization on Indolenine and Anilino Squaraine Thin Films

The impact on chiral aggregation in solution processed and thermally annealed thin films of two indolenine and one anilino squaraines with chiral (S)-citronellyl functionalization at the nitrogen of the squaraine backbone is investigated. A pseudo polymor

Carboxyl-modified near-infrared squaric acid dye as well as preparation method and application thereof

The invention discloses a carboxyl-modified near-infrared squaric acid dye as well as a preparation method and application thereof. The carboxyl-modified near-infrared squaric acid dye is prepared by taking a carboxyl-modified 2-methylbenzothiazole derivative and a dicyanovinyl squaric acid derivative as raw materials. The near-infrared squaric acid dye has relatively good stability and excellent optical performance, and particularly, the water solubility of the dye can be enhanced by carboxylic acid groups. When the near-infrared squaric acid dye is used for detecting parallel and mixed G-quadruplex, the G-quadruplex can interact with dye molecules, and a dye absorption spectrum and a fluorescence emission spectrum are changed while the topological structure of the G-quadruplex is not changed, so that the near-infrared squaric acid dye can be used as a fluorescent probe for detecting the parallel and mixed G-quadruplex.

Near-infrared double-acid dye connected with oxygen ether chain as well as preparation method and application thereof

The invention discloses a near-infrared double-acid dye connected with an oxygen ether chain, and preparation and application thereof. The 2 -methylbenzothiazole derivative and dicyanovinyl modified semiaromatic acid derivative which is linked with an oxygen ether chain is prepared from a raw material. The near-infrared both-side acid dye has good stability and excellent optical performance, and especially the introduction of a sulfonic acid group and an oxygen ether chain can enhance the water solubility of the dye. When the near-infrared double-acid dye is used for detection G - quadruplex, G - quadruplex can interact with the dye molecules, and the change of the dye absorption spectrum and the fluorescence spectrum is caused while G - quadruplex topological structure changes, so that the dye can be used as G - quadruplex. Fluorescent probes for detection.

Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.

An Expedient Synthesis of Tacrine-Squaric Hybrids as Potent, Selective and Dual-Binding Cholinesterase Inhibitors

The restoration of acetylcholine levels in the brain by inhibition of cholinesterases is currently the most successful therapeutic strategy to treat neurodegenerative disorders. In this context, tacrine has been largely investigated as a starting scaffold for the development of promising new anticholinesterases compounds for the treatment of neurodegenerative illnesses, including Alzheimer’s disease. Here we present a series of compounds containing the tacrine nucleus connected with squaric moiety by a diaminoalkylene chain. The compounds were obtained through a simple and short synthetic route and showed high inhibitory activity against acetylcholinesterase (AChE) within nanomolar IC50 (half maximal inhibitory concentration). The molecular modelling study showed that these compounds act as dual-binding inhibitors of AChE, interacting with both catalytic active site (CAS) and peripheral anionic site (PAS) of the enzyme’s binding cavity. The investigated compounds also demonstrated outstanding selectivity for AChE than in butyrylcholinesterase (BuChE). These results evince these compounds as promising agents for the treatment of neurodegenerative disorders and a fuller synthetic scope jointly with complementary biological evaluations are currently under investigation in our laboratory.