80691-81-2

Basic information

• Product Name: 2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester
• Synonyms: 2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester;3,4-diethyl 2,5-diaMinothiophene-3,4-dicarboxylate;Diethyl 2,5-diaMinothiophene-3,4-dicarboxylate;2,5-Diamino-3,4-thiophenedicarboxylic acid diethyl ester
• CAS NO: 80691-81-2
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.29
• Mol File: 80691-81-2.mol

Chemical Properties

• Melting Point: 155-156 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 403.3°C at 760 mmHg
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.343
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C(protect from light)
• PKA: 0.56±0.10(Predicted)
• CAS DataBase Reference: 2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester(80691-81-2)
• EPA Substance Registry System: 2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester(80691-81-2)

Safety Data

• Hazardous Substances Data: 80691-81-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its distinct structural properties allow for the creation of molecules with potential therapeutic applications, contributing to the advancement of drug discovery and innovation.
Used in Polymer Industry:
In the polymer industry, 2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester is utilized as a building block in the synthesis of novel polymers. Its chemical reactivity and structural versatility enable the production of polymers with tailored properties, such as improved strength, flexibility, or thermal stability, for various applications.
Used in Dyes Production:
2,5-Diaminothiophene-3,4-dicarboxylic acid diethyl ester is employed as a key intermediate in the production of dyes. Its ability to participate in various chemical reactions allows for the synthesis of dyes with unique color properties and improved performance characteristics, such as enhanced colorfastness and stability. This makes it a valuable component in the development of new dyes for various industries, including textiles, plastics, and printing.

InChI:InChI=1/C10H14N2O4S/c1-3-15-9(13)5-6(10(14)16-4-2)8(12)17-7(5)11/h3-4,11-12H2,1-2H3

Upstream product

• 104680-25-3 diethyl 2-aminothiophene-3,4-dicarboxylate 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 312929-60-5 diethyl 2-amino-5-(3-nitrobenzamido)thiophene-3,4-dicarboxylate 

Relevant articles and documents

Optimized synthesis and simple purification of 2,5-diamino-thiophene-3,4- dicarboxylic acid diethyl ester

A stable diamino thiophene was synthesized in high purity with a three-fold increase in yield over previous reports via simple crystallization using inexpensive reagents. Copyright Taylor & Francis Group, LLC.

Photophysical, crystallographic, and electrochemical characterization of novel conjugated thiopheno azomethines

New conjugated thiopheno azomethines using a stable 2,5-diamino thiophene precursor are presented. The spectroscopic and photophysical studies of these compounds confirm they dissipate their excited state energy predominately by internal conversion and not by intersystem crossing. Crystallographic data show the thermodynamically favourable E isomer is formed and that the highly conjugated azomethines are both linear and planar. Electrochemical oxidation of the azomethine compounds yields a persistent radical cation that cross couples. The resulting oxidative products undergo reversible radical cation formation and exhibit spectroscopic properties that are consistent with an increased degree of conjugation. The Royal Society of Chemistry 2007.

Discovery of diethyl 2,5-diaminothiophene-3,4-dicarboxylate derivatives as potent anticancer and antimicrobial agents and screening of anti-diabetic activity: Synthesis and in vitro biological evaluation. Part 1

Series of diethyl 2,5-diaminothiophene-3,4-dicarboxylate (DDTD) derivatives: azomethines of DDTD (2a el) have been synthesized and screened for their anticancer, antimicrobial and anti-diabetic activities. The novel synthesized compounds were characterize

Synthesis and: In vitro biological evaluation of novel diaminothiophene scaffolds as antitumor and anti-influenza virus agents. Part 2

On the basis of high-throughput screening, fragment-based drug discovery, structure-activity relationships and building block analysis methods, herein we report the synthesis and biological evaluation of a novel series of diethyl 2,5-diaminothiophene-3,4-dicarboxylate derivatives. All of the prepared Schiff bases (with mono-, di- and poly-substituents at the aromatic portion), mono- and bis-amides of diethyl 2,5-diaminothiophene-3,4-dicarboxylate, were evaluated against various human cancer and non-cancerous (only for active compounds) cell lines, as well as influenza A (subtypes FM/1/47/H1N1, hanfang/359/95/H3N2) and B (subtype jifang/13/97) viruses. The obtained results suggest that some selected compounds revealed promising antitumor and antiviral activities and may serve as lead compounds for further drug discovery and development.

A 2,5-diamino -3,4-thiophene dicarboxylate ethyl derivatives preparation method and use

The invention relates to a preparation method and application of ethyl 2,5-diamido-3,4-thienyldicarboxylate derivatives. Sulfur and ethyl cyanoacetate used as raw materials are condensed with substitution benzaldehyde or arylheterocyclo aldehyde under the

Photophysical, crystallographic, and electrochemical characterization of symmetric and unsymmetric self-assembled conjugated thiopheno azomethines

Novel conjugated azomethines consisting uniquely of thiophene units are presented. The highly conjugated compounds were synthesized by simple condensation of a stable diamino thiophene (2) with its complementary thiophene aldehydes. These interesting nitrogen-containing thiophene units exhibit variable reactivity leading to controlled aldehyde addition. Because of the different amino reactivity, a one-pot synthesis of unsymmetric and symmetric conjugated azomethines with varying number of thiophene units was possible by judicious choice of solvent and careful control of reagent stoichiometry. The resulting covalent conjugated connections are both reductively and hydrolytically resistant. The thermodynamically E isomer is formed uniquely for all of the azomethines synthesized, which is confirmed by crystallographic studies. These also demonstrated that the azomethine bonds and the thiophene units are highly planar and linear. The fluorescence and phosphorescence of the thiopheno azomethines measured are similar to those of thiophene analogues currently used in functional devices, but with the advantage of low triplet formation and band-gaps as low as 1.9 eV. The time-resolved and steady-state temperature-dependent photophysics revealed the thiopheno azomethines do not populate extensively their triplet manifold by intersystem crossing. Rather, their excited-state energy is dissipated predominantly by nonradiative means of internal conversion. Quasi-reversible electrochemical radical cation formation of the thiophene units was found. These compounds further undergo electrochemically induced oxidative cross-coupling, resulting in conjugated products that also exhibit reversible radical cation formation.

Tunable spectroscopic and electrochemical properties of conjugated push-push, push-pull and pull-pull thiopheno azomethines

Novel azomethines consisting uniquely of thiophene units were examined. The highly conjugated compounds were prepared by condensing air stable aminothiophenes with 2-thiophene aldehydes, which were substituted with various electronic groups. The resulting azomethines are highly conjugated and are both reductively and hydrolytically resistant. Various electron donating and accepting groups placed in the 2-position of 5-thiophene carboxaldehyde lead to electronically delocalized push-push, pull-pull, and push-pull azomethines. These electronic groups affect both the HOMO and the LUMO levels, which influence the absorption and emission spectra. Colors spanning the entire visible spectrum ranging from yellow to blue are possible with these nitrogen containing conjugated compounds. Excited state deactivation of the singlet excited state occurs predominately by internal conversion while only a small amount of energy is dissipated by intersystem crossing to the triplet state and by fluorescence. The ensuing fluorescence and phosphorescence of the thiopheno azomethines are similar to those of their thiophene analogues currently used in functional devices, but with the advantage of a low triplet state and tunable HOMO-LUMO energy levels extending from 3.0 to 1.9 eV. Quasi-reversible electrochemical radical cation formation is possible while the oxidation potential is dependent on the nature of the electronic group appended to the thiophene. The crystallographic data of the electronic push-push system show the azomethine bonds are planar and linear and they adopt the E isomer. The Royal Society of Chemistry 2007.

Thienylpyrazoloquinolines: Potent Agonists and Inverse Agonists to Benzodiazepine Receptors

Synthesis and structure-activity relationships of a series of 2-(thien-3-yl)-and 2-(thien-2-yl)-2,5-dihydro-3H-pyrazoloquinolin-3-ones are reported.A number of the compounds possessed 1 order of magnitude higher affinity for the receptors than diazepam.Planarity was one of the structural requirements for binding to benzodiazepine receptors.The activities of agonists and inverse agonists were assessed on the basis of inhibition or facilitation of the pentylenetetrazole-induced convulsions, respectively.Thien-3-yl compounds exhibited inverse agonist activity whereas thien-2-yl analogues with a 5'-alkyl group showed agonist activity.Substitution on the quinoline moiety did not enhance in vivo activity.The most potent compounds were the 5-methylthien-3-yl drivative 6a as an inverse agonist and the 5-methylthien-2yl compound 13 a as an agonist.