17639-64-4

Basic information

• Product Name: 1-Tosylpyrrole
• Synonyms: N-TOSYLPYRROLE;1-TOSYLPYRROLE;1-(P-TOLYLSULFONYL)PYRROLE;1-(P-TOLUENESULFONYL)PYRROLE;1-[(4-Methylphenyl)sulphonyl]-1H-pyrrole;1-Tosyl-1H-pyrrole;N-P-Tolylsulfonylpyrrole;N-p-tolylsulfonylpyrrole, (1-tosylpyrrole)
• CAS NO: 17639-64-4
• Molecular Formula: C₁₁H₁₁NO₂S
• Molecular Weight: 221.28
• EINECS: 241-741-1
• Product Categories: Azoles;blocks;Functional Materials;Pyrroles (for Conduting Polymer Research);Reagents for Conducting Polymer Research;pyrrole;Building Blocks;Heterocyclic Building Blocks;Pyrroles;Aromatics;Heterocycles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 17639-64-4.mol

Chemical Properties

• Melting Point: 98-102 °C
• Boiling Point: 377.344 °C at 760 mmHg
• Flash Point: 182.011 °C
• Appearance: Beige to light brown crystalline powder
• Density: 1.21
• Vapor Pressure: 3.71E-05mmHg at 25°C
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -8.34±0.70(Predicted)
• CAS DataBase Reference: 1-Tosylpyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Tosylpyrrole(17639-64-4)
• EPA Substance Registry System: 1-Tosylpyrrole(17639-64-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 17639-64-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Tosylpyrrole is used as a synthetic building block for the creation of various organic compounds. Its tosyl group provides a handle for further functionalization and modification, making it a versatile starting material in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
1-Tosylpyrrole is used as an intermediate in the development of pharmaceutical compounds. Its unique structure and reactivity allow for the creation of novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
1-Tosylpyrrole serves as a model compound for studying the properties and reactivity of pyrrole derivatives. Its use in research helps to advance the understanding of pyrrole chemistry and contributes to the development of new synthetic methods and applications.
Used in Material Science:
1-Tosylpyrrole can be employed in the development of new materials with specific properties, such as conductivity or optical characteristics, by incorporating its unique structure into the material's design.

InChI:InChI=1/C11H15NO2S/c1-10-4-6-11(7-5-10)15(13,14)12-8-2-3-9-12/h4-7H,2-3,8-9H2,1H3

Upstream product

• 109-97-7 pyrrole 
• 98-59-9 p-toluenesulfonyl chloride 
• 82940-42-9 C₁₇H₁₇NO₂S₂ 
• 33210-01-4 2-p-toluenesulfonyl-3,6-dihydro-1,2-thiazine oxide 
• 290306-56-8 2-bromo-1-(p-toluenesulfonyl)pyrrole 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 1253122-27-8 methyl 3-bromo-1-tosyl-1H-pyrrole-2-carboxylate 
• 50487-72-4 N,N-Diallyltosylamide 
• 346587-69-7 N-(buta-2,3-dien-1-yl)-4-methylbenzenesulfonamide 
• 16851-72-2 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole 
• 70-55-3 toluene-4-sulfonamide 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 123-73-9 crotonaldehyde 
• 107-02-8 acrolein 

Downstream Products

• 139261-90-8 3-benzoyl-N-p-toluenesulfonylpyrrole 
• 152171-06-7 1-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]propan-1-one 
• 152171-08-9 2-methyl-1-[1-((4-methylphenyl)sulfonyl)-1H-pyrrol-3-yl]propan-1-one 
• 129667-08-9 3-cyclohexanoyl-1-tosylpyrrole 
• 129667-06-7 2-cyclohexanoyl-1-tosylpyrrole 
• 152171-07-8 2-phenyl-1-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]ethanone 
• 132951-37-2 1-tosyl-3-octadecanoylpyrrole 
• 1393442-27-7 [1-(Toluene-4-sulfonyl)-1H-pyrrol-3-yl]-p-tolyl-methanone 
• 112561-42-9 4-<1-<(4-Methylphenyl)sulfonyl>-2-pyrrolyl>-4-oxobutyric acid 
• 194352-59-5 4-oxo-4-(1-tosyl-1H-pyrrol-3-yl)butanoic acid 
• 220105-73-7 1-(toluene-4-sulfonyl)pyrrole-2-carbonitrile 
• 129666-99-5 2-acetyl-1-(4-toluenesulfonyl)pyrrole 
• 849939-22-6 3,4-dibromo-1-(4-methylbenzenesulfonyl)-1H-pyrrole 

Relevant articles and documents

Condensation reactions of a nitrodienamine with organocopper and alkyllithium reagents prepared from pyrrole derivatives

Condensation reactions of a nitrodienamine (1) with Grignard, organocopper and alkyllithium reagents prepared from pyrrole derivatives were investigated.

Catalytic, Interrupted Formal Homo-Nazarov Cyclization with (Hetero)arenes: Access to α-(Hetero)aryl Cyclohexanones

The first examples of a Lewis-acid catalyzed (hetero)arene interrupted, formal homo-Nazarov cyclization have been disclosed. Using SnCl4 as the catalyst, alkenyl cyclopropyl ketones undergo ring-opening cyclization to form six-membered cyclic oxyallyl cations. Subsequent intermolecular Friedel-Crafts-type arylation with various electron-rich arenes and heteroarenes provides functionalized α-(hetero)arylated cyclohexanones, a scaffold present in many natural products and bioactive compounds, in yields up to 88% and diastereomeric ratios up to 12:1. Regiospecific arylation occurs at the α-carbon of the oxyallyl cation due to polarization caused by the ester group.

Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.

Synthesis of a New Phorbazole and Its Derivatives

Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.

Pyrrole Hemithioindigo Antimitotics with Near-Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single-Cell Precision**

We report the first cellular application of the emerging near-quantitative photoswitch pyrrole hemithioindigo, by rationally designing photopharmaceutical PHTub inhibitors of the cytoskeletal protein tubulin. PHTubs allow simultaneous visible-light imaging and photoswitching in live cells, delivering cell-precise photomodulation of microtubule dynamics, and photocontrol over cell cycle progression and cell death. This is the first acute use of a hemithioindigo photopharmaceutical for high-spatiotemporal-resolution biological control in live cells. It additionally demonstrates the utility of near-quantitative photoswitches, by enabling a dark-active design to overcome residual background activity during cellular photopatterning. This work opens up new horizons for high-precision microtubule research using PHTubs and shows the cellular applicability of pyrrole hemithioindigo as a valuable scaffold for photocontrol of a range of other biological targets.

Paramagnetic calix[4]porphyrin compound and preparation method thereof

The invention discloses a paramagnetic calix[4]porphyrin compound and a preparation method thereof. Monopyrrole is used as a starting raw material, an electron-rich pyrene group is introduced to a beta position of the monopyrrole to obtain 3-pyrenyl pyrro

Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor

Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.

Synthesis of 3-hetarylpyrroles by Suzuki–Miyaura cross-coupling

1-[tert-Butyl(diphenyl)silyl]pyrrol-3-ylboronic acid was obtained from pyrrole in three steps. Its Suzuki–Miyaura cross-coupling with functionalized pyridinyl and pyrimidinyl bromides afforded new promising 3-hetaryl-1H-pyrroles.

Synthesis of N -Sulfonyl- and N -Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf) 2/s

Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds

Here we report Rh(II)-catalyzed monocyclopropanation reactions on pyrroles in the presence of aryldiazoacetates, providing the corresponding dearomatized products with high levels of enantioselectivity (up to >99% ee). Under the catalysis of Rh2/sub