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

Different sources of media describe the Description of 1072-83-9 differently. You can refer to the following data:
1. 2-acetyl pyrrole is a colorless or yellow liquid. It occurs naturally in cereals and cereal product and has an odor reminiscent of walnut, licorice, baked bread, baked hazelnut, and fish. It is used as a food additive, such as in cocoa, rum, brandy, caramel.
2. Methyl 2-pyrrolyl ketone is like bread, walnut, licorice. May be prepared from pyrryl magnesium iodide and acetyl chloride; a volatile flavor component in roasted filberts.

Chemical Properties

Different sources of media describe the Chemical Properties of 1072-83-9 differently. You can refer to the following data:
1. Methyl-2-pyrrolyl ketone has an odor reminiscent of bread, walnut and licorice
2. white to beige crystalline powder

Occurrence

Reported 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.

Uses

Different sources of media describe the Uses of 1072-83-9 differently. You can refer to the following data:
1. 2-Acetylpyrrole has been used in the synthesis of 2-acetyl-1-pyrroline.
2. hepatoprotectant, organoleptic

Definition

ChEBI: A pyrrole carrying an acetyl substituent at the 2-position.

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

General Description

2-Acetylpyrrole undergoes alkylation reaction with alkyl iodide in benzene/solid KOH system in the presence of 18-crown-6 to yield the corresponding 1-alkyl derivative.

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

Upstream product

• 109-97-7 pyrrole 
• 593-53-3 Methyl fluoride 
• 201230-82-2 carbon monoxide 
• 21872-75-3 diethoxy(methyl)carbenium tetrafluoroborate 
• 50-99-7 D-glucose 
• 56-40-6 glycine 
• 4205-23-6 D-gulose 
• 4429-05-4 N-(1-deoxy-D-fructos-1-yl)-L-glycine 
• 156210-87-6 2-acetyl-5-methylsulfonylpyrrole 
• 2280-44-6 D-Glucose 
• 105356-49-8 2,4-dioxo-4-pyrrol-2-yl-butyric acid ethyl ester 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 56423-57-5 2-(1-hydroxyethyl)pyrrole 

Downstream Products

• 18023-29-5 2-acetylpyrrole-5-carbonitrile 
• 80242-22-4 2-acetylpyrrole-4-carbonitrile 
• 129055-87-4 1-[1-(2-Chloromethyl-benzyl)-1H-pyrrol-2-yl]-ethanone 
• 119479-51-5 (S)-α-Methyl-N-<1-(2-pyrrolyl)ethyliden>phenylmethanamin 
• 81643-06-3 (S)-α-methyl-N-[1-(2-pyrrolyl)ethylidene]benzenemethanamine 
• 39741-41-8 1-Ethyl-2-acetylpyrrole 
• 121805-97-8 1-propyl-2-acetylpyrrole 
• 63547-61-5 1,1'-(1H-pyrrole-2,4-diyl)bis(ethan-1-one) 
• 932-16-1 N-methyl-2-acetylpyrrole 
• 1072-82-8 3-acetylpyrrole 
• 53391-62-1 2-chloro-1-(1H-pyrrol-2-yl)ethanone 
• 134161-64-1 2-thioacetylpyrrole 
• 634-97-9 pyrrole-2-carboxyl acid 
• 158366-45-1 1-Nitro-2-acetylpyrrole 

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.

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.