52707-46-7

Usage

Uses

Used in Organic Light-Emitting Diodes (OLEDs):
2-Thienylpyrrole is utilized as a key component in the development of OLEDs due to its electronic properties, which contribute to the efficient emission of light in these devices. Its incorporation enhances the performance and stability of OLEDs, making it a valuable material for display and lighting technologies.
Used in the Synthesis of Heterocyclic Compounds:
As a building block, 2-Thienylpyrrole is employed in the synthesis of various heterocyclic compounds, which are essential in pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for the creation of novel compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
2-Thienylpyrrole has been investigated for its potential biological activities, showing promise as an anti-inflammatory and anticancer agent. Its ability to modulate inflammatory pathways and exhibit cytotoxic effects on cancer cells positions it as a potential therapeutic candidate for the treatment of various diseases.
Used in Organometallic Chemistry:
2-Thienylpyrrole has been explored as a potential ligand for the coordination of transition metal ions in organometallic chemistry. Its coordination properties enable the formation of new organometallic complexes with potential applications in catalysis, materials science, and other areas.

InChI:InChI=1/C8H7NS/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6,9H

Upstream product

• 1956-45-2 2-acetylthiophene oxime 
• 74-86-2 acetylene 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 106-93-4 ethylene dibromide 
• 1003-09-4 2-bromothiophene 
• 7697-45-2 sodium pyrrolide 
• 107-06-2 1,2-dichloro-ethane 
• 88-15-3 2-Acetylthiophene 
• 1428235-80-6 1-(thiophen-2-yl)but-3-en-1-one oxime 
• 99768-07-7 1-thiophen-2-yl-but-3-en-1-one 
• 71787-54-7 1-(thiophen-2-yl)but-3-en-1-ol 
• 98-03-3 thiophene-2-carbaldehyde 
• 1616603-27-0 C₁₀H₁₁NO₂S 
• 158293-42-6 4-methyl-N-(thiophen-2-ylmethylene)benzenesulfonamide 

Downstream Products

• 1359619-31-0 1-[(Z)-2-phenylethenyl]-2-(2-thienyl)-1H-pyrrole 
• 1447031-60-8 2-[1,1-biphenyl]-4-yl-5-{2,2,2-trifluoro-1-[5-(2-thienyl)-1H-pyrrol-2-yl]ethyl}-1H-pyrrole 
• 1447031-66-4 2-[1,1-biphenyl]-4-yl-5-{1-[5-(1,1-biphenyl)-4-yl-1H-pyrrol-2-yl]-2,2,2-trifluoroethyl}-1H-pyrrole 
• 1447031-62-0 2-[1,1-biphenyl]-4-yl-3-phenyl-5-{2,2,2-trifluoro-1-[5-(2-thienyl)-1Hpyrrol-2-yl]ethyl}-1H-pyrrole 
• 1447031-72-2 4,4-difluoro-3-[(1,1-biphenyl)-4-yl]-5-(2-thienyl)-8-trifluoromethyl-4-bora-3a,4a-diaza-s-indacene 
• 1447031-74-4 4,4-difluoro-3-[(1,1-biphenyl)-4-yl]-2-phenyl-5-(2-thienyl)-8-trifluoromethyl-4-bora-3a,4a-diaza-s-indacene 

Relevant academic research and scientific papers

Synthesis of 2,2′-bipyrroles and 2,2′-thienylpyrroles from donor-acceptor cyclopropanes and 2-cyanoheteroles

(Equation presented) Two new series of 2,2′-bipyrroles and 2,2′-thienylpyrroles have been prepared by trimethylsilyl trifluoromethanesulfonate (TMSOTf)-mediated reaction of donor-acceptor cyclopropanes with 2-cyanopyrroles and 2-cyanothiophene, respectively. This method opens the door toward a wide variety of unsymmetrical bipyrroles and thienylpyrroles.

NIR-Absorbing Dye Based on BF2-Bridged Azafulvene Dimer as a Strong Electron-Accepting Unit

BF2-bridged azafulvene dimers designed to be strong electron-accepting units were selectively synthesized using a bulky base. Single-crystal X-ray diffraction analysis revealed that the high electron-accepting ability of this structure stems from the contribution of the ?-conjugation mode of the azafulvene dimer upon formation of B-N coordination bonds. As a result of the low-lying LUMO energy of this electron-accepting unit, the corresponding D-A-D dye exhibits an intense NIR absorption band at 922 nm, which tails up to 1150 nm, while significant absorption bands in the visible region are absent. As a NIR dye this molecule exhibits moreover exceptional photostability and resistance to oxidation by atmospheric oxygen, even in dilute solution.

Metal-Free Photocatalyzed Cross Coupling of Bromoheteroarenes with Pyrroles

The excited radical anion of rhodamine 6G reduces heteroaryl bromides and chlorides to generate heteroaryl radicals that were successively trapped by pyrroles for the synthesis of heteroaromatic biaryls in moderate to excellent yields. The synthetically important photoredox catalytic C-H heteroarylation reaction works for a broad range of brominated electron-rich heteroarenes and chlorinated heteroarenes bearing electron withdrawing groups. In addition, this methodology was applied to the formal synthesis of a benzimidazole derivative II with interesting pharmacological properties.

Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane

2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2-4 h), the yields of pyrroles ranging 11-85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions.

One-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dibromoethane in the system KOH-DMSO

Dibutyl ketone, cyclohexanone, acetophenone, α-tetralone, and methyl 2-thienyl ketone were converted into the corresponding 2,3-substituted pyrroles by reaction with hydroxylamine hydrochloride and 1,2-dibromoethane in the system KOH-DMSO.

Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: A facile synthesis of 2-arylpyrroles

A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions. the Partner Organisations 2014.

Synthesis and optical properties of difluorobora-s-diazaindacene dyes with trifluoromethyl meso-substituents

A series of meso-CF3-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes with aryl and hetaryl substituents at the C-3 and C-5 positions, both symmetric and asymmetric, have been synthesized in 36-90 % yields by a new strategy involving as the key step the condensation of 2,2,2-trifluoro-1-(5- arylpyrrol-2-yl)-1-ethanols with diverse 2-arylpyrroles. The starting 2,2,2-trifluoro-1-(5-arylpyrrol-2-yl)-1-ethanols are easily prepared by reduction of the available 2-trifluoroacetyl-5-arylpyrroles. The synthesized dyes fluoresce in a longer wavelength region (626-698 nm) with high quantum yield (0.84-0.99). A new strategy for the synthesis of highly efficient symmetric and asymmetric BODIPY fluorophores that combine trifluoromethyl and 3,5-aryl substituents has been developed. The key step is the P 2O5-promoted condensation of 2,2,2-trifluoro-1-(5- arylpyrrol-2-yl)-1-ethanols with diverse 2-arylpyrroles. Copyright

Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles

A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 °C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole - phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole - phenylacetylene and 2-(2-thienyl)pyrrole - phenylacetylene, respectively).

General route to symmetric and asymmetric meso -CF3-3(5)- aryl(hetaryl)- and 3,5-diaryl(dihetaryl)-BODIPY dyes

A general efficient route to hitherto inaccessible symmetric and asymmetric meso-CF3-BODIPY dyes has been developed. The key stages include the reduction of available 2-trifluoroacetylpyrroles to the corresponding alcohols which are further condensed with pyrroles. The method allows the BODIPY with 3(5)aryl(hetaryl) and 3,5-diaryl(hetaryl) substituents to be readily assembled. The BODIPY dyes synthesized fluoresce (?f = 0.56-1.00) in the 560-680 nm region.

Synthesis and optical properties of 2-(Benzo[b]thiophene-3-yl)pyrroles and a new bodipy fluorophore (BODIPY = 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene)

2-(Benzo[b]thiophene-3-yl)-1-vinylpyrrole has been synthesized directly from 3-acetylbenzo[b]thiophene oxime and acetylene (flow system, KOH-DMSO, 120 °C, 5 h) in 68% yield. Devinylation of the synthesized pyrrole (Hg(OAc)CU2, NaBH4, 50 °C) led to the corresponding 2-(benzo[b]thio-phene-3-yl)pyrrole in 63% yield. Tri-fluoroacetylation of both the pyrroles with trifluoroacetic anhydride (80 °C, 1 h) gave the corresponding 5-trifluor-oacetyl pyrroles in 97% and 76% yields, respectively. 2-(Benzo[b]thio-phene-3-yl)pyrrole was reacted subsequently with mesityl aldehyde, 2,3-di-chloro-5,6-dicyano-1,4-benzoquinone (DDQ), and BF 3·OEt2 to afford 4,4-di-fluoro-3,5- diT(benzo[CAGHRUENb]thiophene-3-yl)-8-mesityl-4-bora-3a,4a-diaza-s-inda-cene, a representative of the novel BODIPY fluorophore family (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), in 34% overall yield. The synthesized pyrroles exhibit promising optical properties (absorption and emission spectra, nonlinear optical (NLO) features), superior to existing analogues. The BODIPY fluorophore displays an intense red-shifted fluorescence emission in CH2Cl2(625 nm, 0.84 fluorescence quantum yield) that is fully preserved in the solid state.