81294-16-8

Basic information

• Product Name: 3 2':5' 3 -TERTHIOPHENE
• Synonyms: 2,5-di(thiophen-3-yl)thiophene
• CAS NO: 81294-16-8
• Molecular Formula: C12H8S3
• Molecular Weight: 248.39
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 81294-16-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 175-181 °C(lit.)
• Boiling Point: 315.6°Cat760mmHg
• Flash Point: 106.8°C
• Appearance: /
• Density: 1.318g/cm³
• CAS DataBase Reference: 3 2':5' 3 -TERTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3 2':5' 3 -TERTHIOPHENE(81294-16-8)
• EPA Substance Registry System: 3 2':5' 3 -TERTHIOPHENE(81294-16-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 81294-16-8(Hazardous Substances Data)

Usage

General Description

3,2':5',3-terthiophene is a heterocyclic compound consisting of a central thiophene ring with three carbon-carbon double bonds. It is a sulfur-containing organic compound with a molecular formula of C8H6S2. 3,2':5',3-terthiophene is commonly used as a building block in the synthesis of organic semiconductors, conducting polymers, and other electronic materials due to its unique electrical and optical properties. It is also utilized in the production of OLEDs (Organic Light Emitting Diodes) and in the field of organic electronics for its potential use in photovoltaic devices and thin-film transistors. The compound can also be used as a model system for studying the electronic properties of pi-conjugated materials.

Upstream product

• 3141-27-3 2,5-dibromothiophen 
• 70161-87-4 (thiophen-3-yl)trimethylstannane 
• 81294-14-6 1,4-bis(thiophen-3-yl)buta-1,3-diyne 
• 81294-09-9 3-(2,2-dibromoethenyl)-thiophene 
• 67237-53-0 3-ethynylthiophene 
• 101306-14-3 1,4-di(3'-thienyl)1,4-butanedione 
• 6165-69-1 Thien-3-ylboronic acid 

Relevant articles and documents

Cobalt-Catalyzed Glaser-type Homocoupling Reaction

A highly efficient cobalt-catalyzed homocoupling of terminal alkynes with di-tert-butyldiaziridinone as the oxidant has been developed. The protocol tolerates a wide array of terminal alkynes, both activated and unactivated alkynes, to afford the corresponding conjugated 1,3-diynes. The mild reaction conditions further allow late-stage homocoupling of alkynes derived from complex natural products.

Synthesis of thiophene oligomers via organotin compounds

A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes. Substituted bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 3-trimethylstannylthiophene. The latter reagent couples with bromoaromatics, bromoheteroaromatics and 2,5-dibromothiophenes to give the corresponding 3-arylthiophenes, 3-heteroarylthiophenes and terthiophenes, respectively. 2-Trimethylstannylthiophene couples with 2,5-dibromo-3-arylthi ophenes to give 3-aryl-α-terthiophenes. The structures of the new compounds were confirmed by elemental analysis, mass spectrometry, 1H- and 13C-NMR spectral data.

SYNTHESIS OF 3,2':5',3''-TERTHIOPHENE AND 2,5-DI(3'-THIENYL)FURAN

Synthesis of 3,2':5',3''-terthiophene (2) and 2,5-di(3-thienyl)furan (6) has been achieved from 1,4-di(3'-thienyl) 1,4-butanedione (3) which in turn was prepared by the hypervalent iodine oxidation of 3-acetylthiophene silyl enol ether (5).Mass spectra of 2 and 6 are also discussed.