86688-88-2

Basic information

• Product Name: 2-ACETYL-1-(PHENYLSULFONYL)PYRROLE
• Synonyms: 1-[1-(PHENYLSULFONYL)-1H-PYRROL-2-YL]ETHAN-1-ONE;2-ACETYL-1-(PHENYLSULFONYL)PYRROLE;1-[1-(phenylsulphonyl)-1H-pyrrol-2-yl]ethan-1-one;2-ACETYL-N-BENZENESULFONYLPYRROLE;1-[1-(benzenesulfonyl)pyrrol-2-yl]ethanone
• CAS NO: 86688-88-2
• Molecular Formula: C₁₂H₁₁NO₃S
• Molecular Weight: 249.29
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrroles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 86688-88-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 95-96 °C(lit.)
• Boiling Point: 435.7°C at 760 mmHg
• Flash Point: 217.3°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 8.61E-08mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 2-ACETYL-1-(PHENYLSULFONYL)PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYL-1-(PHENYLSULFONYL)PYRROLE(86688-88-2)
• EPA Substance Registry System: 2-ACETYL-1-(PHENYLSULFONYL)PYRROLE(86688-88-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 86688-88-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H11NO3S/c1-10(14)12-8-5-9-13(12)17(15,16)11-6-3-2-4-7-11/h2-9H,1H3

Upstream product

• 16851-82-4 N-phenylsulfonylpyrrole 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 130896-50-3 1-Benzenesulfonyl-2-(1-trimethylsilanyloxy-vinyl)-1H-pyrrole 
• 1072-83-9 2-Acetylpyrrole 
• 97188-25-5 1-Benzenesulfonyl-2-ethyl-1H-pyrrole 
• 103085-22-9 2-ethyl-1-(phenylsulfonyl)pyrrolidine 
• 131543-97-0 2-ethyl-1-(phenylsulfonyl)-3-pyrroline 
• 741288-81-3 1-(6-methoxy-pyridin-3-yl)-5-[1-(phenylsulfonyl)pyrrol-2-yl] pyrazole-3-carboxylic acid ethyl ester 
• 875553-34-7 4-[1-(phenylsulfonyl)-1H-pyrrol-2-yl]-2, 4-dioxobutanoic acid methyl ester 
• 1404195-23-8 2-iodo-N-(1-(1-(phenylsulfonyl)-1H-pyrrol-2-yl)ethylidene)aniline 
• 1404195-25-0 4-(bromomethyl)-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-26-1 4-((6-chloro-9H-purin-9-yl)methyl)-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-27-2 3-((3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinolin-4-yl)methyl)quinazolin-4(3H)-one 
• 1404195-24-9 4-methyl-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-30-7 C₁₈H₁₄ClIN₂O₂S 
• 1404195-34-1 7-chloro-4-methyl-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 

Relevant articles and documents

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Regioselective Synthesis of Acylpyrroles

The regioselective synthesis of several pyrrole derivatives is described.AlCl3-catalyzed acylation reactions of 1-(phenylsulfonyl)pyrrole (1) give 3-acyl derivatives, whereas the corresponding BF3*OEt2-catalyzed reactions give 2-acyl derivatives predominantly.Mild alkaline hydrolysis gives the corresponding acyl-1H-pyrroles in excellent yields.AlCl3-catalyzed reactions of 1 with 1,1-dichloromethyl methyl ether and oxalyl chloride give 1-(phenylsulfonyl)-2-formylpyrrole (6) and 1-(phenylsulfonyl)-2-(chlorocarbonyl)pyrrole (7), respectively. 3-Pyrrolylacetic acid (10) was prepared by thallium(III) nitrate promoted rearrangement of 1-(phenylsulfonyl)-3-acetylpyrrole (2a).Trifluoroacetic anhydride catalyzed cyclization of 4-butyric acid (14) gives 1-(phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole (17).Attempts to cyclize 14 at the 4-position have been unsuccessful.