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
• Article Data: 51

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

Description

2-Acetylpyrrole, also known as Methyl 2-pyrrolyl ketone, is a colorless or yellow liquid that occurs naturally in various cereals and cereal products. It is characterized by an odor reminiscent of walnut, licorice, baked bread, baked hazelnut, and fish. This organic compound is used as a flavoring agent in the food industry and is also involved in the synthesis of other compounds.

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

• 609-41-6 N-acetylpyrrole 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 109-97-7 pyrrole 
• 127-19-5 N,N-dimethyl acetamide 
• 108-24-7 acetic anhydride 
• 60-29-7 diethyl ether 
• 75-36-5 acetyl chloride 
• 127-09-3 sodium acetate 
• 562-90-3 tetraacetoxysilane 
• 16199-06-7 potassium pyrrolide 
• 74-88-4 methyl iodide 
• 1072-82-8 3-acetylpyrrole 
• 593-53-3 Methyl fluoride 
• 201230-82-2 carbon monoxide 

Downstream Products

• 412013-37-7 1-(5-dimethylaminomethyl-pyrrol-2-yl)-ethanone 
• 911052-96-5 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 31685-34-4 2,5-diacetylpyrrole 
• 22634-73-7 (E)-3-(4-methylphenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 911052-94-3 (E)-3-(2-chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 22563-62-8 (E)-3-(4-nitrophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 22563-48-0 (2E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 22563-52-6 (2E)-3-(4-methoxyphenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 111260-60-7 (2E,4E)-5-phenyl-1-(1H-pyrrol-2-yl)penta-2,4-dien-1-one 
• 22563-55-9 (E)-3-(4-(dimethylamino)phenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one 
• 1551-06-0 2-ethyl-1H-pyrrole 
• 56423-57-5 2-(1-hydroxyethyl)pyrrole 
• 51333-64-3 1-(4-bromo-1H-pyrrol-2-yl)ethan-1-one 
• 393819-18-6 2-acetyl-3,4,5-tribromopyrrole 

Relevant articles and documents

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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 %).

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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.

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.

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.