51792-34-8

Basic information

• Product Name: 3,4-Dimethoxythiophene
• Synonyms: 3,4-DIMETHOXYTHIOPHENE 98%;3,4-dimethoxytiophene;,4-diMethoxythiophene;3,4-diMethoxy thiophene (DMOT);3,4- twoMethoxythiophene;DMOT;3,4-DIMETHOXYTHIOPHENE;AKOS BBS-00006359
• CAS NO: 51792-34-8
• Molecular Formula: C₆H₈O₂S
• Molecular Weight: 144.19
• EINECS: 603-128-0
• Product Categories: Thiophenes;Organic Electronics and Photonics;Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Thiophene Series;OLED
• Mol File: 51792-34-8.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 100-102 °C (10-11 mmHg)
• Flash Point: 224 ºF
• Appearance: /
• Density: 1.209
• Vapor Pressure: 1.01mmHg at 25°C
• Refractive Index: 1.5409
• Storage Temp.: ?20°C
• Water Solubility: Miscible with organic solvents. Slightly miscible with water.
• CAS DataBase Reference: 3,4-Dimethoxythiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxythiophene(51792-34-8)
• EPA Substance Registry System: 3,4-Dimethoxythiophene(51792-34-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 51792-34-8(Hazardous Substances Data)

Usage

Description

3,4-Dimethoxythiophene (DMOT) is a monomer and a precursor that can be synthesized by a ring closure reaction of 2,3-dimethoxy-1,3-butadiene and sulfur dichloride in a hexane medium. It is an oligothiophene, which is a type of organic compound with alternating single and double bonds between carbon and sulfur atoms. DMOT is majorly used in the development of electroactive materials for various applications in the field of organic electronics.

Uses

Used in Electronic Materials Industry:
3,4-Dimethoxythiophene is used as an electronic materials intermediate for the development of electroactive materials. Its unique structure and properties make it suitable for use in organic electronics, where it can contribute to the performance and functionality of electronic devices.
Used in Photoinduced Energy Transfer Research:
3,4-Dimethoxythiophene is used as a starting material in the synthesis of porphyrin dyads, which are used to study photoinduced energy transfer. This application is crucial for understanding and improving the efficiency of energy transfer processes in various technologies, such as solar cells and light-emitting diodes (LEDs).
Used in the Synthesis of N2S2-N4 Porphyrin Dyads:
DMOT serves as a building block in the synthesis of an N2S2-N4 porphyrin dyad, which is also used to study photoinduced energy transfer. The development of such dyads can lead to advancements in the design and optimization of materials for energy conversion and storage applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 2956, 1951 DOI: 10.1021/ja01150a525

InChI:InChI=1/C6H8O2S/c1-7-5-3-9-4-6(5)8-2/h3-4H,1-2H3

Upstream product

• 177364-96-4 3,4-dimethoxythiophene-2,5-dicarboxylic acid 
• 3588-31-6 2,3-dimethoxy-1,3-butadiene 
• 3141-26-2 3,4-dibromothiophene 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 58416-04-9 3,4-dihydroxythiophene-2,5-dicarboxylic acid dimethyl ester 
• 77-78-1 dimethyl sulfate 
• 177364-92-0 diethyl 3,4-dimethoxythiophene-2,5-dicarboxylate 
• 118851-98-2 3,4-dimethoxythiophene-2,5-dicarboxylic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 14282-59-8 thiophene-3,4-diol 

Downstream Products

• 1202754-48-0 2,5-dibromo ProDOT 
• 146796-02-3 (2,3-dihydrothieno[3,4-b][1,4]dioxin-3-yl)methanol 
• 1434567-24-4 3,3-Bis(4-nitrobenzyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine 

Relevant articles and documents

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Poly(thieno[3,4- b ]-1,4-oxathiane): Medium effect on electropolymerization and electrochromic performance

The asymmetrical sulfur analog of 3,4-ethylenedioxythiophene (EDOT), thieno[3,4-b]-1,4-oxathiane (EOTT), was synthesized, and its electropolymerization was comparatively investigated by employing different solvent-electrolyte systems (room temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF6), CH2Cl2-Bu4NPF6, and CH2Cl2-BmimPF6). Further, the effect of solvents and supporting electrolytes on the structure, morphology, electrochemical, electronic, and optical properties and electrochromic performance of the obtained poly(thieno[3,4-b]-1,4-oxathiane) (PEOTT) films were minutely studied. PEOTT film with a band gap (Eg) of about 1.6 eV could be facilely electrodeposited in all the solvent-electrolytes and displayed excellent electroactivity, outstanding redox stability in a wide potential window, and improved thermal stability. Cyclic voltammetry showed that EOTT could be electropolymerized at a lower oxidation potential in BmimPF6 (～1.0 V vs Ag/AgCl) due to several advantanges of RTIL BmimPF6 itself, such as high intrinsic conductivity and mild chemical conditions, etc., and the resulting PEOTT film exhibited compact morphology with better electroactivity and stability and higher electrical conductivity. On the other hand, PEOTT films from all the sovent-electrolytes also showed the electrochromic nature by color changing from gray blue to green, and further kinetic studies revealed that PEOTT had decent contrast ratios (36%), higher coloration efficiencies (212 cm2/C in BmimPF6), low switching voltages, moderate response time (1.2 s), excellent stability, and color persistence. From these results, PEOTT provides more plentiful electrochromic colors and holds promise for display applications.

Method for synthesizing 3,4-dimethoxythiophene

The invention relates to a method for synthesizing 3,4-dimethoxythiophene. The method comprises steps as follows: S1, 2,5-dimethyl dicarboxylate-3,4-sodium thiophene diol and dimethyl sulfate are subjected to a heating reaction in an organic solvent, and 3,4-dimethoxythiophene-2,5-dimethyl dicarboxylate is obtained; S2, 3,4-dimethoxythiophene-2,5-dimethyl dicarboxylate is subjected to the heatingreaction with strong base in an alkylbenzene organic solvent with the boiling point not lower than 200 DEG C, then strong acid is added for acidification, and 3,4-dimethoxythiophene-2-formic acid is obtained; S3, 3,4-dimethoxythiophene-2-formic acid is subjected to a reduced-pressure heating reaction in a long-chain amine organic solvent with the boiling point not lower than 300 DEG C, and 3,4-dimethoxythiophene is obtained. The method is low in production cost, low in energy consumption and high in product yield, the organic solvents can be recycled, particularly, no catalyst is used in the step of decarboxylation, so that the cost is greatly reduced, and environmental pollution is reduced.

BLUE ELECTROCHROMIC COMPOUND, PREPARATION METHOD AND SUBASSEMBLY THEREOF

One class of blue thiophene electrochromic compounds include 3,4-(2,2-bis(2-oxo-3-phenylpropyl))propylenedioxythiophene, 3,4-(2,2-bis(2-oxo-3-phenylbutyl))propylenedioxythiophene, and 3,4-(2,2-bis(2-oxo-3-phenylamyl))propylenedioxythiophene. The thiophene electrochromic compounds can change color between blue and transparency. The thiophene compounds can be electropolymerized on the surface of the ITO glass to form a film. The film has characteristics of low driving voltage (within ±1V), fast response time, and large transmittance difference between colored-state and bleached-state (up to 77.5%). The thiophene electrochromic compounds can be used in the electrochromic window, rearview mirror, electrochomeric display, and the like.

Process for production of thiophene derivative

[Purpose] thiophene for preparing derivatives method, among other things, purity thiophene derivatives obtained in high yield by provides a method. [Constitution] halogenated thiophene and an alkali metal alkoxide seed alcohol solvent during is a process, alcohol solvent is regulated so as to have reaction outflow by including for a manipulation type well. , dialkoxy thiophene which comprises the step of obtaining an, oxygen atoms and thiophene dialkoxy said including compound or the like, an evacuating product caused by reaction while type well. outflow reaction to reaction step of reacting a carboxylic acid component characterized by including, of thiophene derivatives is manufacturing method. (by machine translation)