2-Thienylpyrrole

Base Information

• Chemical Name: 2-Thienylpyrrole
• CAS No.: 52707-46-7
• Molecular Formula: C8H7NS
• Molecular Weight: 149.216
• Hs Code.: 2934999090
• Mol file: 52707-46-7.mol

Synonyms:2-(2-Thienyl)-1H-pyrrole;2-(2-Thienyl)pyrrole;2-(2'-Thienyl)pyrrole;

Chemical Property of 2-Thienylpyrrole

Chemical Property:

• Vapor Pressure: 0.00168mmHg at 25°C
• Melting Point: 78-80 °C
• Refractive Index: 1.631
• Boiling Point: 303.3 °C at 760 mmHg
• PKA: 17.09±0.50(Predicted)
• Flash Point: 140.3 °C
• PSA: 44.03000
• Density: 1.217 g/cm³
• LogP: 2.74320

Purity/Quality:

99% ^*data from raw suppliers

2-(2-THIENYL)PYRROLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Thienylpyrrole

There total 26 articles about 2-Thienylpyrrole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-thiophen-2-yl-1H-3-carboxylic acid ethyl ester → 2-(thiophen-2-yl)-1H-pyrrole (52707-46-7)

Guidance literature:

With sodium hydroxide; In ethylene glycol; at 160 ℃; for 0.0833333h;

DOI:10.1021/ol049857h

Reference yield: 71.0%

2-bromothiophene (1003-09-4) + sodium pyrrolide (7697-45-2) → 2-(thiophen-2-yl)-1H-pyrrole (52707-46-7)

Guidance literature:

sodium pyrrolide; With zinc(II) chloride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; johnphos; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere;

2-bromothiophene; In tetrahydrofuran; at 100 ℃; for 17h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02056

Reference yield: 61.5%

3-(1,3-dioxolan-2-yl)-1-(2-thienyl)-1-propanone (145654-80-4) → 2-(thiophen-2-yl)-1H-pyrrole (52707-46-7) + 2,4-bis(2-thienyl)-1H-indole (145654-81-5)

Guidance literature:

With ammonium acetate; acetic anhydride; acetic acid; Heating;

DOI:10.1016/S0040-4020(01)92285-9

upstream raw materials:

2-acetylthiophene oxime

acetylene

1,2-dichloro-ethane

O-(2-vinyl) methyl 2-thienyl ketoxime

Downstream raw materials:

1-[(Z)-2-phenylethenyl]-2-(2-thienyl)-1H-pyrrole

2-[1,1-biphenyl]-4-yl-5-{2,2,2-trifluoro-1-[5-(2-thienyl)-1H-pyrrol-2-yl]ethyl}-1H-pyrrole

2-[1,1-biphenyl]-4-yl-5-{1-[5-(1,1-biphenyl)-4-yl-1H-pyrrol-2-yl]-2,2,2-trifluoroethyl}-1H-pyrrole

2-[1,1-biphenyl]-4-yl-3-phenyl-5-{2,2,2-trifluoro-1-[5-(2-thienyl)-1Hpyrrol-2-yl]ethyl}-1H-pyrrole

Refernces

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

10.1016/j.tet.2011.12.050

The research aims to develop a straightforward and efficient method for synthesizing nitrogen stilbene analogs, specifically 1-styrylpyrroles, without the use of transition metals. The study utilizes a superbasic KOH/DMSO system to facilitate the hydroamination of arylacetylenes with various substituted pyrroles at moderate temperatures (90–120 °C). The purpose of this research is to provide a general and atom-economic route for the synthesis of these compounds, which have potential applications in drug design, optoelectronic materials, and as precursors for molecular optical switches. The key chemicals used include pyrroles (both unsubstituted and substituted), arylacetylenes (such as 2-Phenylpyrrole and 2-(2-Thienyl)pyrrole), and ethynylpyridine. The results show that the reaction proceeds readily, yielding 1-styrylpyrroles in good to excellent yields (up to 94%) with high stereoselectivity, depending on the structure of the reactants and reaction conditions. The study concludes that this transition metal-free approach is a promising method for synthesizing nitrogen stilbene analogs, offering a general and efficient route that can be tailored to produce specific E- or Z-stereoisomers, thus expanding the toolkit for chemists working on the development of new materials and pharmaceuticals.

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