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

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

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

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

Downstream Products

• 95602-75-8 E-1-(3,4-Dimethoxy-2-thienyl)-3-(4-methoxyphenyl)-2-propen-1-on 
• 158962-92-6 3,4-ethylenedisulfanylthiophene 
• 406940-42-9 3,3-dibenzyl-3,4-dihydro-2H-thienopheno[3,4-b][1,4]dioxepine 
• 126213-50-1 3,4-(ethylenedioxy)thiophene 
• 496801-01-5 2,5-bis-(phenylhydroxymethyl)-3,4-dimethoxythiophene 
• 701209-98-5 3,3-bis(bromomethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine 
• 857419-46-6 2-(chloromethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine 
• 259139-19-0 3,4-(2,2-diethylpropane-1,3-diyldioxy)thiophene 
• 155861-77-1 3,4-(propane-1,3-diyldioxy)thiophene 
• 634591-75-6 3,3-bis[[(2-ethylhexyl)oxy]methyl]-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin 
• 496801-09-3 2,5-bis-(phenylhydroxymethyl)-3,4-dibutoxythiophene 
• 496801-13-9 2,5-bis-(phenylhydroxymethyl)-3,4-dioctyloxythiophene 
• 496801-18-4 2,5-bis-(phenylhydroxymethyl)-3,4-bis-(dodecyloxy)thiophene 

Relevant articles and documents

Optimisation of substitution at the 2- and 5- positions of 3,4-dialkoxythiophenes via the Mannich reaction: The influences of steric crowding, electrophile reactivity and temperature

A number of 3,4-dialkoxythiophene compounds have been synthesised and their reactivities assessed via the Mannich reaction with secondary amines. These reactions surprisingly gave the bis-Mannich bases substituted at the 2- and 5-positions as well as the expected mono-Mannich bases substituted at the 2-position. Conditions were optimised to give symmetrical bis-2,5-Mannich bases in one step and asymmetrical bis-2,5-Mannich bases in two steps. Several bis(thien-2-ylmethyl)amines derived from 3,4-dialkoxythiophenes are reported, their synthesis being performed under both normal and high dilution conditions. Some syntheses also afforded the (thien-2-ylmethyl)amine oligomers. Further substitution of the bis(thien-2-ylmethyl)amines at the 5-position via the Mannich reaction also proved successful. The factors affecting the yields and substitution patterns are discussed, together with molecular modelling of the spatial requirements.

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.

A 3, 4 - dimethoxy synthetic method of thiophene (by machine translation)

The invention discloses a 3, 4 - dimethoxy thiophene synthesis method, the method will be 2, 5 - dicarboxylic acid dimethyl ester - 3, 4 - dimethoxy thiophene dissolved in dimethyl formamide in aqueous solution, then adding the pectins catalyst, at a temperature of 130 - 180 °C, pressure is 0 - 10 kg/cm2 Reaction (table) 5 - 18 h after, filtered, pressure reducing rectification to get 3, 4 - dimethoxy thiophene, wherein filtering and rectification are in thermal insulation a pressure maintaining state. The method utilizes the pectins technology, has eliminated saponification, acidified and other intermediate links, shortens the synthetic route, reduces the consumption of raw materials, in particular reduces the production of waste aqueous solution, reduces the integrated cost, simplify the post-processing procedure, the whole synthetic route more environment-friendly, safer, more efficient. (by machine translation)

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)

Synthesis of 4,4′-dimethoxy-3,3′-bithiophene

Abstract Reaction between 3,3′-dibromothiophene and sodium methylate/methanol in the presence of KI/CuO afforded 3-bromo-4-methoxythiophene as a major product. It was transformed into 4,4′-dimethoxy-3,3′-bithiophene by using Pd(OAc)2 as a catalyst and agarose as a ligand. The conditions of the reaction were mild with an acceptable yield of 20 %. The product was characterized by MS, 1H NMR, and its spectra of UV-Vis and cyclic voltammetry were given. Graphical Abstract: 4,4′-dimethoxy-3,3′-bithiophene was synthesized from 3-bromo-4-methyloxy thiophene in the homogeneous system formed by water and agarose.[Figure not available: see fulltext.]

Electrochemical sensor based on f-SWCNT and carboxylic group functionalized PEDOT for the sensitive determination of bisphenol A

A simple, sensitive, and reliable method for the voltammetric determination of bisphenol A (BPA) by using carboxylic group functionalized single-walled carbon nanotubes (f-SWCNT)/carboxylic-functionalized poly(3,4- ethylenedioxythiophene) (PC4) complex modified glassy carbon electrode (GCE) has been successfully developed. The electrochemical behavior of BPA at the surface of the modified electrode is investigated by electrochemical techniques. The cyclic voltammetry results show that the as-prepared electrode exhibits strong catalytic activity toward the oxidation of BPA with a well-defined anodic peak at 0.623 V in PBS (0.1 mol/L, pH 7.0). The surface morphology of the 3D network of composite film is beneficial for the adsorption of analytes. Under the optimized conditions, the oxidation peak current is proportional to BPA concentration in the range between 0.099 and 5.794 μmol/L (R2 = 0.9989), with a limit of detection of 0.032 μmol/L (S/N = 3). The enhanced performance of the sensor can be attributed to the excellent electrocatalytic property of f-SWCNT and the extraordinary conductivity of PC4. Furthermore, the proposed modified electrode displays high stability and good reproducibility. The good result on the voltammetric determination of BPA also indicates that the as-fabricated modified electrode will be a good candidate for the electrochemical determination and analysis of BPA.

Electrochromic enhancement of poly(3,4-ethylenedioxythiophene) films functionalized with hydroxymethyl and ethylene oxide

2-((2,3-Dihydrothieno[3,4-b]dioxin-2-yl)methoxy)methyl oxirane (EDOT-MO) was successfully synthesized by the reaction of epichlorohydrin with hydroxymethylated-3,4-ethylenedioxylthiophene (EDOT-MeOH), which was synthesized via a simple four-step sequence. Poly(hydroxymethylated-3,4- ethylenedioxylthiophene) (PEDOT-MeOH) and poly(2-((2,3-dihydrothieno[3,4-b] dioxin-2-yl)methoxy)methyl oxirane) (PEDOT-MO) were electrosynthesized through electropolymerization of EDOT-MeOH and EDOT-MO, respectively. Structural, electrochemical, optical, and thermal properties of as-formed polymers were investigated by FTIR, cyclic voltammetry, UV-vis, and thermogravimetry. Spectroelectrochemistry studies demonstrated that PEDOT-MeOH and PEDOT-MO could be reversibly oxidized and reduced accompany with obvious color changes. Further kinetic studies demonstrated that the introduction of hydroxymethyl or ethylene oxide group significantly improved electrochromic properties of 3,4-ethylenedioxythiophene (PEDOT) and resulted in high contrast ratios (57.3% at 585 nm) and coloration efficiencies (338.5 cm2 C-1), low switching voltages, and fast response time.

Robust PEDOT films by covalent bonding to substrates using in tandem sol-gel, surface initiated free-radical and redox polymerization

Poly(3,4-ethylenedioxythiophene), PEDOT, films are used as antistatic coatings on electrically insulating substrates such as plastic and glass. A novel method for the synthesis of conducting PEDOT films on insulators relies on sol-gel chemistry to attach a di-Si(OEt)3 functionalized free radical initiator (AIBN) on oxidized surfaces, followed by: (a) attachment of 3,4-(vinylenedioxy)thiophene (VDOT: an analogue to EDOT susceptible to radical addition through its vinylenedioxy group); and, (b) oxidative (with FeCl 3) co-polymerization of surface-confined VDOT with 3,4-ethylenedioxythiophene (EDOT). In conjunction with classical photolithography, the method yields thin (～150 nm) yet dense, pinhole-free (confirmed electrochemically), hard (>6H), extremely adhesive (5B), patterned, highly conducting (52 mho cm-1) films. The process is applied mainly on glass but it works equally well on oxidized metal surfaces (aluminum, steel, Pt). Control studies related to "grafting from" with surface-confined AIBN were conducted by growing inexpensive poly(styrene) and poly(methylmethacrylate) films.