175202-58-1

Basic information

• Product Name: 3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE
• Synonyms: 3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE;3,4-DIMETHYLTHIENO(B)THIOPHENE;BUTTPARK 33\11-63;3,4-DIMETHYLTHIENO(B)THIOPHENE 97%
• CAS NO: 175202-58-1
• Molecular Formula: C₈H₈S₂
• Molecular Weight: 168.28
• Mol File: 175202-58-1.mol

Chemical Properties

• Melting Point: 72-74°C
• Boiling Point: 272.6°Cat760mmHg
• Flash Point: 86.4°C
• Appearance: /
• Density: 1.245g/cm³
• Vapor Pressure: 0.0101mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE(175202-58-1)
• EPA Substance Registry System: 3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE(175202-58-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 175202-58-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE is used as a building block for synthesizing materials with unique electronic properties, suitable for various applications in the organic electronics industry.
Used in Organic Field-Effect Transistors (OFETs):
3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE is used as a semiconductor material in organic field-effect transistors, due to its electron-donating ability and structural properties, which contribute to improved device performance.
Used in Organic Solar Cells:
In the solar energy industry, 3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE is used as a component in organic solar cells, where its electron-donating properties enhance the efficiency of energy conversion.
Used in Organic Light-Emitting Diodes (OLEDs):
3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE is utilized as a material in organic light-emitting diodes, benefiting from its unique electronic properties that contribute to improved light emission and device performance.

InChI:InChI=1/C8H8S2/c1-5-3-9-8-7(5)6(2)4-10-8/h3-4H,1-2H3

Upstream product

• 175202-55-8 3,4-dimethylthieno[2,3-b]thiophene-2,5-dicarboxylic acid 
• 152487-69-9 diethyl 3,4-dimethylthieno<2,3-b>thiophen-2,5-dicarboxylate 
• 123-54-6 acetylacetone 
• 250-84-0 thieno[2,3-b]thiophene 
• 75-52-5 nitromethane 
• 75-15-0 carbon disulfide 
• 75-07-0 acetaldehyde 
• 105-53-3 diethyl malonate 
• 141-82-2 malonic acid 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 159709-36-1 3,5-dimethyl thieno(2,3-b) thiophene 2-carboxaldehyde 

Relevant articles and documents

3,4-dimethylthiophene[2,3-b]thiophthene synthesis method

A 3,4-dimethylthiophene[2,3-b]thiophthene synthesis method includes steps: 1) mixing carbon disulfide, malonic ester and DMF, and heating to reflux; 2) adding a catalyst and 40-50wt% acetaldehyde aqueous solution into a mixed system obtained at the step 1), feeding shielding gas, heating the system to 150-180 DEG C, pressurizing to 4-7 atmospheric pressures, and performing reaction for 10-12h, wherein the catalyst refers to potassium fluoride loaded palladium on carbon; 3) separating and purifying to obtain a product. By conditions of self-made catalyst, pressurized reaction and the like, 3,4-dimethylthiophene[2,3-b]thiophthene can be synthesized by one-step reaction, and the reaction yield reaches 97% or above. In addition, a reaction process and aftertreatment operations are simple, and related raw materials are low in cost.

Method for one-step synthesis of 3, 4-dimethylthieno[2, 3-b]thiophene

The invention discloses a method for one-step synthesis of 3, 4-dimethylthieno[2, 3-b]thiophene. The method comprises 1) mixing thieno[2, 3-b]thiophene, substituted methane, an organic base and a catalyst, and carrying out a reaction process under conditions of pressure and protective gas, wherein the catalyst is rhodium carbon having rhodium content of 5wt%, and 2) separating and purifying the reaction system to obtain a product 3, 4-dimethylthieno[2, 3-b]thiophene. Under the pressure auxiliary condition, in the presence of the catalyst, under action of the organic base, groups at 3th and 4th sites of the thieno[2, 3-b]thiophene undergo a nucleophilic reaction to produce 3, 4-dimethylthieno[2, 3-b]thiophene. The reaction yield is 96% or more.

Synthesis, complexation, and fluorescence behavior of 3,4-dimethylthieno[2, 3-b]thiophene carrying two monoaza-15-crown-5 ether groups

A novel fluoroionophore 1 based on 3,4-dimethylthieno[2,3-b]thiophene bearing two monoaza-15-crown-5 ethers at 3- and 4-positions was prepared. UV-vis and fluorescence responses of compound 1 upon the addition of alkali and alkaline earth metal cations were evaluated in acetonitrile solution. Receptor 1 showed unique response for Ba2+ due to the formation of an intramolecular sandwich complex.

Efficient one pot preparation of variously substituted thieno[2,3-b]thiophene

An efficient one pot access to variously substituted thieno[2,3-b]thiophene is described. The title compounds were obtained from 1,3-dicarbonyl or equivalent compounds, carbon disulfide and halomethyl derivatives in good to high yields and fully characterized.