5231-87-8

Basic information

• Product Name: Diethyl squarate
• Synonyms: 3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE, 98 %;DiethylSquarate98%;3,4-DIETHOXYCYCLOBUTANE-1,2-DIONE;Diethyl squarate, Squaric acid diethyl ester;SQUARIC ACID DIETHYL ESTER,(DIETHYL SQUARATE, 3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE);DIETHOXYCYCLOBUTENEDIONE;3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE 98%;SQUARICACIDDIETHYLESTER/3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE
• CAS NO: 5231-87-8
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.16
• Product Categories: Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;Ring Systems;Aluminium foil bag/Fluoride bottle or on your request
• Mol File: 5231-87-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: 13-18 °C
• Boiling Point: 95 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to light brownish/Liquid
• Density: 1.15 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000226mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: insoluble
• BRN: 640626
• CAS DataBase Reference: Diethyl squarate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl squarate(5231-87-8)
• EPA Substance Registry System: Diethyl squarate(5231-87-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-42/43
• Safety Statements: 7-26-37/39-24-23
• WGK Germany: 3
• RTECS: GU1772466
• F: 10
• Hazardous Substances Data: 5231-87-8(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to light brownish liquid

Uses

Different sources of media describe the Uses of 5231-87-8 differently. You can refer to the following data:
1. Diethyl squarate is an intermediate for pharma products, for photochemicals used in the dry-view process, in synthesis of photosensitive squaraine dyes (eg. laser dyes used in CD-Rom) and as intermediate for functional polymers.
2. 3,4-Dethoxy-3-cyclobutene-1,2-dione is used as a starting material for synthesis of furanones and quinones. It undergoes ethoxy substitution with amines and unsaturated organosilanes.

General Description

The reaction of 3,4-diethoxy-3-cyclobutene-1,2-dione (squaric acid diethyl ester) with glycosylamines (formed by reducing oligosaccharides) was studied. The derivatives formed were linked to amino-functionalized lipids, solids or proteins.

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

Downstream Products

• 29950-11-6 3-ethoxy-4-morpholinocyclobut-3-ene-1,2-dione 
• 158599-28-1 2,3-diethoxy-4-hydroxy-4-phenacyl-2-cyclobutenone 
• 37512-97-3 2-(2-Ethoxy-3,4-dioxo-cyclobut-1-enyl)-3-oxo-3-phenyl-propionic acid ethyl ester 
• 100749-12-0 3,4-bis(cyclohexylamino)cyclobut-3-ene-1,2-dione 
• 175204-28-1 3-(cyclohexylamino)-4-ethoxycyclobut-3-ene-1,2-dione 
• 37512-99-5 2-(2-Hydroxy-3,4-dioxo-cyclobut-1-enyl)-5,5-dimethyl-cyclohexane-1,3-dione 
• 175204-30-5 Quadratsaeure-ethylester-<4-carboxy-anilid> 
• 42132-09-2 3-(ethoxy)-4-(phenylamino)-3-cyclobutene-1,2-dione 
• 33512-89-9 3,4-bis(phenylamino)cyclobut-3-ene-1,2-dione 
• 1121-15-9 3,4-dimethylcyclobut-3-ene-1,2-dione 
• 22118-95-2 3-ethoxy-4-phenyl-3-cyclobutylene-1,2-dione 
• 22119-01-3 3-Amino-4-phenyl-3-cyclobuten-1,2-dion 
• 5231-89-0 3,4-diamino-cyclobut-3-ene-1,2-dione 
• 1026912-46-8 3-[(3-Benzyloxycarbonylamino-propyl)-(2-ethoxy-3,4-dioxo-cyclobut-1-enyl)-amino]-propionic acid ethyl ester 

Relevant articles and documents

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.

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.

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.

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