16851-82-4

Basic information

• Product Name: 1-(PHENYLSULFONYL)PYRROLE
• Synonyms: BUTTPARK 95\50-50;1-(PHENYLSULFONYL)PYRROLE;1-(PHENYLSULPHONYL)PYRROLE;1-(PHENYLSULFONYL)-1H-PYRROLE;N-BENZENESULFONYLPYRROLE;N-Benzenesulphonylpyrrole;1-(phenylsulphonyl)-1H-pyrrole;1-(BENZENESULFONYL)PYRROLE, 97%
• CAS NO: 16851-82-4
• Molecular Formula: C₁₀H₉NO₂S
• Molecular Weight: 207.25
• EINECS: -0
• Product Categories: Pyrroles & Indoles;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Pyrroles
• Mol File: 16851-82-4.mol
• Article Data: 38

Chemical Properties

• Melting Point: 88-91 °C(lit.)
• Boiling Point: 368.9 °C at 760 mmHg
• Flash Point: 176.9 °C
• Appearance: Beige to light brown/Crystals or Crystalline Powder
• Density: 1.2784 (rough estimate)
• Vapor Pressure: 1.23E-05mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -8.50±0.70(Predicted)
• BRN: 1619427
• CAS DataBase Reference: 1-(PHENYLSULFONYL)PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(PHENYLSULFONYL)PYRROLE(16851-82-4)
• EPA Substance Registry System: 1-(PHENYLSULFONYL)PYRROLE(16851-82-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 16851-82-4(Hazardous Substances Data)

Usage

Description

1-(Phenylsulfonyl)pyrrole, also known as 1-phenylsulfonyl-1H-pyrrole, is a heterocyclic building block with a phenylsulfonyl group attached to the nitrogen atom of the pyrrole ring. This group serves as an N-blocking and directing group in various organic syntheses, making it a versatile compound for chemical reactions and pharmaceutical applications.

Uses

Used in Pharmaceutical Synthesis:
1-(Phenylsulfonyl)pyrrole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its phenylsulfonyl group acts as a blocking and directing group, facilitating the formation of complex molecular structures with specific properties.
Used in Organic Synthesis:
1-(Phenylsulfonyl)pyrrole is used as a building block in organic synthesis for the creation of a wide range of chemical compounds. Its unique structure allows for various functional group transformations and reactions, making it a valuable component in the development of new molecules with specific applications.
Used in the Synthesis of 1-(Phenylsulfonyl)pyrrole-2-boronic Acid:
1-(Phenylsulfonyl)pyrrole is used as a starting material for the synthesis of 1-(phenylsulfonyl)pyrrole-2-boronic acid, which can be achieved through lithiation of the parent compound. This boronic acid derivative can be further utilized in the synthesis of various organic compounds and pharmaceuticals.
Used in the Synthesis of 1-Phenylsulfonyl-1H-Pyrrole-3-Sulfonyl Chloride Derivatives:
1-(Phenylsulfonyl)pyrrole is also used in the synthesis of 1-phenylsulfonyl-1H-pyrrole-3-sulfonyl chloride derivatives. These derivatives can be obtained by reacting the parent compound with appropriate reagents, and they can be further transformed into sulfonamide derivatives by reaction with nitrogen nucleophiles. These sulfonamide derivatives have potential applications in the pharmaceutical industry as they can exhibit various biological activities.

InChI:InChI=1/C10H9NO2S/c12-14(13,11-8-4-5-9-11)10-6-2-1-3-7-10/h1-9H

Upstream product

• 109-97-7 pyrrole 
• 98-09-9 benzenesulfonyl chloride 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 98-10-2 benzenesulfonamide 
• 25630-24-4 N,N-diallylbenzenesulfonamide 
• 16851-71-1 1-(benzenesulfonyl)-2,5-dihydro-1H-pyrrole 

Downstream Products

• 117379-48-3 4-(1-phenylsulphonylpyrrol-3-yl)-4-oxobut-2-enoic acid 
• 109482-67-9 1-phenylsulfonyl-3-(2-bromo)propionylpyrrole 
• 86688-92-8 4-<1-(Phenylsulfonyl)-2-pyrrolyl>-4-oxobutyric acid 
• 81454-02-6 4-<1-(Phenylsulfonyl)-3-pyrrolyl>-4-oxobutyric acid 
• 141994-98-1 2,5-Dimethyl-3-(1H-pyrrol-3-yl)-pyrazine 
• 141994-93-6 2,5-Dimethyl-3-(1H-pyrrol-2-yl)-pyrazine 
• 141994-97-0 3-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-2,5-dimethyl-pyrazine 
• 141994-96-9 3-(1-Benzenesulfonyl-1H-pyrrol-2-yl)-2,5-dimethyl-pyrazine 
• 97188-23-3 3-ethyl-1-phenylsulfonylpyrrole 
• 97188-25-5 1-Benzenesulfonyl-2-ethyl-1H-pyrrole 
• 97188-24-4 2,5-diethyl-1-(phenylsulfonyl)pyrrole 
• 53876-81-6 1,1-dibenzosulphonylbutane 
• 83819-26-5 Diphenyl-pyrrol-1-yl-methanol 
• 97188-22-2 1-(Phenylsulfonyl)pyrrole-2-carbonitrile 

Relevant articles and documents

Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole

In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles.

Ketorolac impurity C and preparation method and application thereof

The invention discloses a ketorolac impurity C and a preparation method and application thereof. According to the method, the ketorolac impurity C is prepared by taking pyrrole as an initial raw material through a series of reactions such as substitution,

5-MEMBERED HETEROARYLAMINOSULFONAMIDES FOR TREATING CONDITIONS MEDIATED BY DEFICIENT CFTR ACTIVITY

The invention relates to heteroaryl compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

Structural Basis of Metallo-β-lactamase Inhibition by N-Sulfamoylpyrrole-2-carboxylates

Metallo-β-lactamases (MBLs) can efficiently catalyze the hydrolysis of all classes of β-lactam antibiotics except monobactams. While serine-β-lactamase (SBL) inhibitors (e.g., clavulanic acid, avibactam) are established for clinical use, no such MBL inhibitors are available. We report on the synthesis and mechanism of inhibition of N-sulfamoylpyrrole-2-carboxylates (NSPCs) which are potent inhibitors of clinically relevant B1 subclass MBLs, including NDM-1. Crystallography reveals that the N-sulfamoyl NH2 group displaces the dizinc bridging hydroxide/water of the B1 MBLs. Comparison of crystal structures of an NSPC and taniborbactam (VRNX-5133), presently in Phase III clinical trials, shows similar binding modes for the NSPC and the cyclic boronate ring systems. The presence of an NSPC restores meropenem efficacy in clinically derived E. coli and K. pneumoniae blaNDM-1. The results support the potential of NSPCs and related compounds as efficient MBL inhibitors, though further optimization is required for their clinical development.