58416-04-9

Basic information

• Product Name: 3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester
• Synonyms: DIMETHYL 3,4-DIHYDROXYTHIOPHENE-2,5-DICARBOXYLATE;3,4-DIHYDROXY-THIOPHENE-2,5-DICARBOXYLIC ACID DIMETHYL ESTER;3,4-DIHYDROXY-2,5-DICARBOXYTHIOPHENE DIMETHYL ESTER;2,5-Thiophenedicarboxylic acid, 3,4-dihydroxy-, dimethyl ester;Dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate 3,4-Dihydroxy-2,5-dicarboxythiophene dimethyl ester;3,4-Dihydroxy-2,5-thiophenedicarboxylic Acid Dimethyl Ester;Dimethyl 3,4-Dihydroxy-2,5-thiophenedicarboxylate;3,4-Dihydroxy-thioph
• CAS NO: 58416-04-9
• Molecular Formula: C₈H₈O₆S
• Molecular Weight: 232.21
• Mol File: 58416-04-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 182 °C
• Boiling Point: 378.558 °C at 760 mmHg
• Flash Point: 182.745 °C
• Appearance: /
• Density: 1.532 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 8.19±0.20(Predicted)
• CAS DataBase Reference: 3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester(58416-04-9)
• EPA Substance Registry System: 3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester(58416-04-9)

Safety Data

• Hazardous Substances Data: 58416-04-9(Hazardous Substances Data)

Usage

Description

3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester, also known as Dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate, is a white powder chemical compound derived from the thiophene ring system. It is characterized by its reactive functional groups, which make it a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester is used as a key reactant for the synthesis of various bioactive compounds, particularly in the pharmaceutical industry. Its ability to undergo Curtius-like rearrangement reactions allows for the creation of 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems, which are essential in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester serves as an important intermediate for the production of various organic compounds. Its unique structure and reactivity make it a valuable building block for the synthesis of complex molecules, including those with potential applications in materials science, agrochemicals, and other specialty chemicals.
Used in Research and Development:
3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester is also utilized in research and development laboratories for the exploration of novel chemical reactions and the development of new synthetic methodologies. Its versatility in undergoing various chemical transformations makes it a valuable tool for chemists working on the design and synthesis of new molecules with specific properties and applications.

InChI:InChI=1/C8H8O6S/c1-13-7(11)5-3(9)4(10)6(15-5)8(12)14-2/h9-10H,1-2H3

Upstream product

• 553-90-2 Dimethyl oxalate 
• 16002-29-2 dimethyl thiodiglycolate 

Downstream Products

• 146796-02-3 (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methanol 
• 897922-08-6 (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methyl benzoate 
• 51792-34-8 2,3-dimethoxythiophene 
• 118851-98-2 3,4-dimethoxythiophene-2,5-dicarboxylic acid dimethyl ester 
• 18361-03-0 3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid 
• 122372-73-0 12-crown-4 thiophene 
• 14282-58-7 3,4-dihydroxy-2,5-dicarboxylic acid thiophene 

Relevant articles and documents

2,5-Diamide-Substituted Five-Membered Heterocycles: Challenging Molecular Synthons

We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a "closed" conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.