1072-83-9

Basic information

• Product Name: 2-Acetyl pyrrole
• Synonyms: 2-Acetylpyrrole, Methyl 2-pyrrolyl ketone;(2-Pyrrolyl)ethanone;1-(2-Pyrrolyl)-1-ethanone;2-Acetyl-1H-pyrrole;2-Acetylpyrrole ,98%;Methyl(1H-pyrrol-2-yl) ketone;2-Acetylpyrrole,99%;1-(1H-Pyrrol-2-yl)ethan-1-one , tech
• CAS NO: 1072-83-9
• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13
• EINECS: 214-016-2
• Product Categories: ketone;pyrrole;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;API intermediates;Benzenes;Flavor
• Mol File: 1072-83-9.mol

Chemical Properties

• Melting Point: 88-93 °C(lit.)
• Boiling Point: 220 °C(lit.)
• Flash Point: 220°C
• Appearance: White to beige/Crystalline Powder
• Density: 1.1143 (rough estimate)
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: 1.5040 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 14.86±0.50(Predicted)
• BRN: 1882
• CAS DataBase Reference: 2-Acetyl pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetyl pyrrole(1072-83-9)
• EPA Substance Registry System: 2-Acetyl pyrrole(1072-83-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-36/37/38
• Safety Statements: 37/39-26-24/25-36
• WGK Germany: 3
• RTECS: OB5970000
• TSCA: Yes
• Hazardous Substances Data: 1072-83-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Acetylpyrrole is used as a flavoring agent for its distinct odor, which resembles the scent of bread, walnut, and licorice. It is commonly added to products such as cocoa, rum, brandy, and caramel to enhance their flavor profile.
Used in Synthesis:
2-Acetylpyrrole is used in the synthesis of 2-acetyl-1-pyrroline, a compound with applications in various industries.
Used in Hepatoprotection and Organoleptic Properties:
2-Acetylpyrrole serves as a hepatoprotectant, aiding in the protection and maintenance of liver health. Additionally, it contributes to the organoleptic properties of various food products, enhancing their taste and aroma.
Occurrence:
2-Acetylpyrrole is found in essential oils of tobacco leaves, apple, asparagus, onion, baked and fried potato, roasted almonds, wheat bread, cooked chicken, cooked beef and pork, beer, malt whiskey, cocoa, coffee, tea, roasted filberts, and peanuts, peanut butter, potato chips, soybean, coconut, mushrooms, almond, mango, licorice, sweet corn, malt, wort, dried bonito, Bourbon vanilla, chicory root, okra, crab, scallop, and clam.

Preparation

From pyrrole magnesium iodide and acetyl chloride; a volatile flavor component in roasted filberts

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3214, 1983 DOI: 10.1021/jo00167a014Tetrahedron Letters, 26, p. 4649, 1985 DOI: 10.1016/S0040-4039(00)98776-8

InChI:InChI=1/C6H7NO/c1-5(8)6-3-2-4-7-6/h2-4,7H,1H3

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 74-88-4 methyl iodide 
• 1072-82-8 3-acetylpyrrole 
• 109-97-7 pyrrole 
• 593-53-3 Methyl fluoride 
• 201230-82-2 carbon monoxide 
• 101822-46-2 Methyl-[1-(1H-pyrrol-2-yl)-eth-(E)-ylidene]-amine 
• 112816-55-4 2-(2-Methyl-benzo[1,3]oxathiol-2-yl)-1H-pyrrole 
• 76007-20-0 2-N-methylanilinoacetylpyrrole 
• 2280-44-6 D-Glucose 
• 105356-49-8 2,4-dioxo-4-pyrrol-2-yl-butyric acid ethyl ester 
• 56423-57-5 2-(1-hydroxyethyl)pyrrole 
• 57-48-7 D-Fructose 
• 70-18-8 GLUTATHIONE 

Downstream Products

• 634-97-9 pyrrole-2-carboxyl acid 
• 158366-45-1 1-Nitro-2-acetylpyrrole 
• 22563-48-0 (2E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 32116-25-9 5-Nitro-2-acetyl-pyrrol 
• 32116-24-8 5-acetyl-3-nitro-1H-pyrrole 
• 760945-91-3 1-(2-bromo-4-chlorobenzyl)-2-acetylpyrrole 
• 760945-88-8 1-(1-(2-bromobenzyl)-1H-pyrrol-2-yl)ethan-1-one 
• 80242-22-4 2-acetylpyrrole-4-carbonitrile 

Relevant articles and documents

Zinc mediated straightforward access to diacylpyrroles

In this article, we report the preparation of various 2,4- and 2,5-diacylpyrroles via two zinc-mediated acylation reactions of non-protected pyrroles.

A NEW ROUTE FOR MESO-SUBSTITUTED PORPHYRIN

A new synthetic route of meso-substituted porphyrins was esthablished.The method presented here shows wide applicability for the preparation of aryl and alkyl meso-substituted porphyrins.

Kinetic studies on the 1,2-sigmatropic hydrogen shift in the photorearranged intermediate of N-acetylpyrrole: Tunneling effects

The rates for the 1,2-sigmatropic hydrogen and deuterium shifts in the ground state of the photorearranged intermediate of N-acetylpyrrole were directly measured by means of laser flash photolysis in several solvents; (e.g., 0.27 s-1 for 1,2-H shift and 0.12 s-1 for 1,2-D shift in nonpolar methylcyclohexane (MCH) at 293 K). The rate of the 1,2-hydrogen shift was remarkably increased by a basic catalyst, such as triethylamine, alcohols, and water. From the experimental results of temperature and isotope effects, it was shown that the 1,2-sigmatropic hydrogen (or deuterium) shift in MCH proceeds via quantum mechanical tunneling processes at two vibrational energy levels: E = 0 (v = v0) and E = Ev (=2.9 kcal mol-1 for the hydrogen shift or 3.3 kcal mol-1 for the deuterium shift) (v = v1) under experimental conditions. The theoretical considerations for the tunneling mechanism were made by use of the tunnel effect theory proposed by Formosinho. The rates obtained by theoretical calculations were in good agreement with experimental ones. It is noteworthy that the 1,2-sigmatropic hydrogen (or deuterium) shift takes place via the intramolecular process at a low concentration of N-acetylpyrrole (1.7 × 10-4 M) in dehydrated MCH.

Non-acidic mediated friedel-craft reaction of thiophene using EtAlCl 2

Since alkyl Lewis acids are Br?nsted bases, they give a non-acidic reaction media. In this context, acylation of thiophene is investigatedin the presence of EtAlCl2 and non-acidic media. Besides 8 examples of thiophene, one example for pyrrole is synthesized in moderate tohigh yields (up to 99 %).

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.

Efficient microwave-assisted syntheses of a series of novel mono(Imino)Pyrrolyl compounds

A series of novel mono(imino)pyrroles that were hard to prepare under traditional solvent reaction condition were readily synthesized under solvent free condition using microwave chemistry via p-TSA (p-toluenesulfonic acid) catalyzed Schiff base condensation. The structures of the compounds were characterized by means of MS, 1H NMR, IR, elementary analysis and X-ray diffraction analysis. The reactivity of different aromatic amines with 2-acetylpyrrole was discussed.

1,2-Dioximes in the Trofimov reaction

3,3′-Dimethyl-1,1′-divinyl-2,2′-dipyrrole was obtained during the reaction of 3,4-hexanedione dioximes with acetylene under pressure in the potassium hydroxide-DMSO system. In the case of 1,2-cyclohexanedione dioxime 2,2′-dipyrrole and 2-pyridyl- and 2-acylpyrroles were isolated. α-Benzil and α-furil dioximes give 3,4-diphenyl- and 3,4-di(2-furyl)-1,2,5-oxadiazoles respectively in addition to their mono- and divinyl derivatives. 2006 Springer Science+Business Media, Inc.

Entropic Mixing Allows Monomeric-Like Absorption in Neat BODIPY Films

Intermolecular interactions play a crucial role in materials chemistry because they govern thin film morphology. The photophysical properties of films of organic dyes are highly sensitive to the local environment, and a considerable effort has therefore been dedicated to engineering the morphology of organic thin films. Solubilizing side chains can successfully spatially separate chromophores, reducing detrimental intermolecular interactions. However, this strategy is also significantly decreasing achievable dye concentration. Here, five BODIPY derivatives containing small alkyl chains in the α-position were synthesized and photophysically characterized. By blending two or more derivatives, the increase in entropy reduces aggregation and therefore produces films with extreme dye concentration and, at the same time almost solution like absorption properties. Such a film was placed inside an optical cavity and the achieved system was demonstrated to reach the strong exciton-photon coupling regime by virtue of the achieved dye concentration and sharp absorption features of the film.

Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction

Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.