492-97-7

Basic information

• Product Name: 2,2'-BITHIOPHENE
• Synonyms: 2,2'-Bithiophene;2,2μ-Bithienyl, 2,2μ-Dithienyl;2-(2'-Thieno)thiophene;2,2'-Bithiophene,97%;2,2zzhlxy-Bithiophene;2-(Thiophen-2yl) thiophene;2,2′-Bithiophene, >=99%;2-(2-Thienyl)thiophen
• CAS NO: 492-97-7
• Molecular Formula: C₈H₆S₂
• Molecular Weight: 166.26
• EINECS: 207-767-2
• Product Categories: Thiophenes;pharmacetical;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Thiophene Series;Heterocycle-oher series
• Mol File: 492-97-7.mol
• Article Data: 244

Chemical Properties

• Melting Point: 32-33 °C(lit.)
• Boiling Point: 260 °C(lit.)
• Flash Point: >230 °F
• Appearance: white to light yellow crystal powder
• Density: 1.2455 (rough estimate)
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 3039
• CAS DataBase Reference: 2,2'-BITHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-BITHIOPHENE(492-97-7)
• EPA Substance Registry System: 2,2'-BITHIOPHENE(492-97-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 10-23
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 492-97-7(Hazardous Substances Data)

Usage

Description

2,2'-bithiophene is an intermediate widely used for the synthesis of small molecules or polymer semiconductors in application of organic electronics.?It has proven that?2,2'-bithiophene exists as a mixture of the cis-like and the trans-like planar structures. 5,5'-positions of?2,2'-bithiophene are easily accessible for bromination and stannylation to give 5,5'-dibromo-2,2'-bithiophene or 5,5'-trimethylstannyl-2,2'-bithiophene, which can be used for direct arylation reactions.

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 492-97-7 differently. You can refer to the following data:
1. 2,2’Bithiophene is a reactant in the preparation of thienophenyl compounds.
2. 2,2'-Bithiophene is used as a precursor in the preparation of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene , which is used for the synthesis of small molecules and polymer semiconductors for organic field-effect transistor (OFETs), organic light-emitting diode (OLED), Plastic Light Emitting Diode (PLED) and Organic Photovoltaic (OPV) applications. It is associated with aryl iodides and involved in rhodium catalyzed arylation of heteroarenes.
3. 2,2′-Bithiophene can be polymerized to form poly(2,2′-Bithiophene) which can be electrodeposited on indium tin oxide (ITO) substrates for the fabrication of electrochromic devices. It can also be used in the formation of electrode material for the development of supercapacitors.

Definition

ChEBI: A thiophene derivative that consists of two thiophene rings connected by a 2,2'-linkage.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2627, 1986 DOI: 10.1021/jo00364a002Synthetic Communications, 19, p. 307, 1989 DOI: 10.1080/00397918908050983

General Description

2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.

Upstream product

• 188290-36-0 thiophene 
• 30930-49-5 bis(2-thiophenecarbonyl) peroxide 
• 1003-09-4 2-bromothiophene 
• 3437-95-4 2-Iodothiophene 
• 13781-37-8 2-iodo-5-phenylthiophene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 64-17-5 ethanol 
• 109-86-4 2-methoxy-ethanol 
• 110-86-1 pyridine 
• 2786-07-4 2-thienyl lithium 
• 121044-12-0 2-chloro-2,4,4-trimethyl-1,3-dioxa-2-silacyclohexane 
• 7774-74-5 Thiophene-2-thiol 

Downstream Products

• 1081-34-1 2,2':5',2''-terthiophene 
• 144433-90-9 5,5'-bis2,2'-bithiophene 
• 88493-55-4 sexithiophene 
• 670-54-2 tetracyanoethylene radical cation 
• 149228-14-8 5,5'-di-tert-butyl-2,2'-bithiophene 
• 5660-45-7 quinquethienyl 
• 26985-31-9 methyl viologen cation radical 
• 32358-91-1 1-(2,2'-bithienyl-5-yl)propan-1-one 
• 58400-12-7 (2,2'-bithiophen-5-yl)(phenyl)methanone 
• 3515-18-2 5-acetyl-2,2'-bithiophene 
• 18494-73-0 5,5'-di(1-oxoethyl)-2,2'-bithiophene 
• 3779-27-9 2,2'-bithiophene-5-carboxaldehyde 
• 16303-58-5 5,5'-dimethyl-2,2'-dithiophene 
• 4805-22-5 5,5'-dibromo-2,2'-bisthiophene 

Relevant articles and documents

Desorption/ionization on self-assembled monolayer surfaces (DIAMS)

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Receptor- And ligand-based study on novel 2,2′-bithienyl derivatives as non-peptidic AANAT inhibitors

Arylalkylamine N-acetyl transferase (serotonin N-acetyl transferase, AANAT) is a critical enzyme in the light-mediated regulation of melatonin production and circadian rythm. With the objective of discovering new chemical entities with inhibitory potencies against AANAT, a medium-throughput screening campaign was performed on a chemolibrary. We found a class of molecules based on a 2,2′-bithienyl scaffold, and compound 1 emerged as a first hit. Herein, we describe our progress from hit discovery and to optimization of this new class of compounds. To complete the study, computational approaches were carried out: a docking study which provided insights into the plausible binding modes of these new AANAT inhibitors and a three-dimensional quantitative structure-activity relationship study that applied comparative molecular field analysis (CoMFA) methodology. Several CoMFA models were developed (variable alignments and options), and the best predictive one yields good statistical results (q2 = 0.744, r2 = 0.891, and s = 0.273). The resulting CoMFA contour maps were used to illustrate the pharmacomodulations relevant to the biological activities in this series of analogs and to design new active inhibitors. This novel series of 2,2′-bithienyl derivatives gives new insights into the design of AANAT inhibitors.

Laser flash photolysis study on the photoinduccd reactions of 3,3′-bridged bithiophenes

Photophysical properties and photoinduced reactions of 3,3′-bridged-2,2′-bithiophenes {dithieno[3,2-b:2′,3′-d]-thiophene, 4H-cyclopenta[2,1-b:3,4-b′]dithiophene, and 4H-dithieno[3,2-b;2′,3′-d]pyrrole (DTP)} and 2,2′-bithiophene (BT) were investigated by observing the transient absorption spectra in the visible and near-IR regions using nanosecond laser flash photolysis. Fluorescence quantum yields for the bridged bithiophenes were low compared with that for BT. An especially low quantum yield for DTP in acetonitrile was attributed to an addition reaction with the solvent. The triplet energy of BT was the lowest amongst the examined bithiophenes, indicating some conformational change in the triplet state. Triplet-energy-transfer reactions at diffusion limited rates were confirmed between bithiophenes and triplet-energy donors or acceptors. Photochemical generation of the radical cations of the bithiophenes was confirmed by the transient absorption spectra, which show good correspondence with those observed in γ-ray radiolysis. It was found that the triplet quenching rates of the electron-transfer reactions were small when the Gibbs energy change for the reaction was ≥ -25 kJ mol-1. The observed tendency agreed with the semi-empirical equation of Rehm-Weller. The generated radical cations decay according to a second-order function, indicating deactivation by a back electron-transfer reaction.

Preparation and Reactions of Dichlorodithienogermoles

The reaction of 3,3′-dilithiobithiophenes with tetrachlorogermane afforded 4,4-dichlorodithienogermoles, which readily underwent substitution on the central germanium atom. Reactions of a dichlorodithienogermole with LiAlH4, MeLi, Me2NC6H4Li, and C6F5MgBr gave the corresponding Ge-substituted products. Dihydrodithienogermole obtained from the reaction with LiAlH4 was further treated with LDA to give a dimer whose structure was verified by a single-crystal X-ray diffraction (XRD) study. Hydrolysis of dichlorodithienogermoles provided cyclotetragermoxanes. Their optical properties were examined with respect to the UV absorption and fluorescence spectra. It was found that one of the cyclotetragermoxanes responded to a nitorobenzene vapor in the solid state, decreasing the PL intensity.

A novel approach to a one-pot synthesis of unsubstituted oligo(α-thiophenes)

Oligo(α-thiophenes) α-4T and α-8T were prepared by the following one-pot sequential conversions: thiophene (T) → α-2T → α-4T → α-8T. PdCl2-induced coupling of a mono-α-mercuration derivative of each of the n-mers T, α-2T, and α-4T was applied in these conversions.

Copper(I)-catalysed homocoupling of organosilicon compounds: Synthesis of biaryls, dienes and diynes

Copper(I) iodide catalyses the homocoupling of aryl-, alkenyl- and alkynyl-substituted chloro- or fluorodimethylsilanes under mild conditions to afford biaryls, dienes and diynes, respectively.

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air

Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.