129666-99-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetyl-1-tosylpyrrole is utilized as a precursor in the synthesis of biologically active compounds, playing a crucial role in the development of new pharmaceuticals. Its unique structure and reactivity allow for the creation of diverse molecules with potential therapeutic applications.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 2-Acetyl-1-tosylpyrrole serves as a starting material for the production of bioactive compounds intended for use in agriculture, such as pesticides and herbicides, to improve crop protection and yield.
Used in Academic Research:
2-Acetyl-1-tosylpyrrole is also employed in academic research settings, where it is used to study the reactivity and chemical properties of pyrrole derivatives. This research contributes to the broader understanding of organic chemistry and can lead to the discovery of new synthetic pathways and applications for this class of compounds.

InChI:InChI=1/C13H13NO3S/c1-10-5-7-12(8-6-10)18(16,17)14-9-3-4-13(14)11(2)15/h3-9H,1-2H3

Upstream product

• 17639-64-4 N-p-toluenesulfonylpyrrole 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 1072-83-9 2-Acetylpyrrole 
• 98-59-9 p-toluenesulfonyl chloride 
• 64-19-7 acetic acid 

Downstream Products

• 1551-06-0 2-ethyl-1H-pyrrole 
• 1426385-29-6 1-(5-ethyl-1H-pyrrol-2-yl)-1-(4-methoxyphenyl)-4-methylpentan-3-one 
• 1426385-30-9 C₁₉H₂₃NO 
• 1426385-31-0 C₁₉H₂₃NO 
• 1313534-06-3 (E)-1-(1-tosyl-1H-pyrrol-2-yl)ethanone O-acetyl oxime 
• 1313534-67-6 7-methyl-4,5-dipropyl-1-tosyl-1H-pyrrolo[2,3-c]pyridine 
• 31685-34-4 2,5-diacetylpyrrole 
• 63547-61-5 1,1'-(1H-pyrrole-2,4-diyl)bis(ethan-1-one) 
• 1072-83-9 2-Acetylpyrrole 

Relevant academic research and scientific papers

A new method for the acylation of pyrroles

N-Tosylpyrroles can be very efficiently acylated by carboxylic acids in the presence of trifluoroacetic anhydride to give only the 2-acyl derivatives. N-Tosylpyrroles can be very efficiently converted into the corresponding 2-acylpyrroles by reaction with carboxylic acids and trifluoroacetic anhydride; little or none of the isomeric 3-acyl derivatives are formed.

Integration of oxidative arylation with sulfonyl migration: One-pot tandem synthesis of densely functionalized (NH)-pyrroles

A one-pot synthesis of 2-aryl-3-alkyl/aryl-sulfonyl-(NH)-pyrroles from N-sulfonylpyrroles, developed for the first time, via palladium-catalyzed oxidative C-2 arylation followed by sulfonyl migration is described. The simple, easy access to the highly functionalized free-NH pyrroles secures opportunities for the preparation of compounds with promising biological activities in contemporary organic synthesis. The event of sulfonyl migration from pyrrole-N to C-3 is thermodynamically favored as revealed by density functional methods. The different plausible mechanisms for the migration of the sulfonyl group are also discussed.

Acylation of N-p-toluenesulfonylpyrrole under Friedel-Crafts conditions: evidence for organoaluminum intermediates

The Friedel-Crafts acylation of N-p-toluenesulfonylpyrrole under Friedel-Crafts conditions has been reinvestigated. Evidence is presented in support of the hypothesis that when AlCl3 is used as the Lewis acid, acylation proceeds via reaction of

Pyrroles substituted by oligonucleotides

The invention relates to novel pyrrole derivatives of the formula (I) which make it possible to immobilize and address oligonucleotides by electropolymerization. Said invention also relates to thus produced electroactive polymers and to methods for using

Synthesis and properties of polyquinolines and polyanthrazolines containing pyrrole units in the main chain

A series of eight new polyquinolines and polyanthrazolines with pyrrole isomeric units in main chain were synthesized and characterized. The new polymers showed high glass transition temperatures (Tg = 242-339°C) and excellent thermal stability (T5% = 398-536°C in air, TGA). Compared to the series of polyanthrazolines, the series of polyquinolines exhibited higher thermal stability, better solubility in common organic solvents, and lower maximum absorption wavelengths (λmaxa). Polyanthrazolines with 2,5-pyrrole linkage showed an unusually high λmaxa (565 nm) and small band gap (2.02 eV). All polymers in solution had low photoluminescence quantum yields between 10-2% and 10-5% and excited-state lifetimes of 0.28-1.29 ns. The effects of molecular structure, especially pyrrole linkage structures, on the electronic structure, thermodynamics, and some of the optical properties of the polymers were explored. A model of hydrogen bonds in the main chain of the polymers was suggested to explain the difference in the properties of the isomer polymers. In addition, a polyquinoline (PBM) was chosen to examine the proton conductivity; the result indicated that the PBM/H3PO4 complex exhibited a high conductivity of 1.5 × 10-3 S cm-1 at 157°C. The new polymers are expected to have improved proton-conducting properties for the application as the membranes in fuel cells.

PREPARATION OF ALKYL-SUBSTITUTED INDOLES IN THE BENZENE PORTION. Part 3

Three-step synthesis of 7- and 4-alkyl-1-tosylindoles (9 and 10) was accomplished by combination of the Friedel-Crafts acylation of 4, and the treatment of 7 and 8 with H2SO4 in 2-propanol as illustrated in Chart 2.Further a novel synthetic method of 16 was devised from 14 by way of 15.