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1072-83-9

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1072-83-9 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

Check Digit Verification of cas no

The CAS Registry Mumber 1072-83-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 2 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1072-83:
(6*1)+(5*0)+(4*7)+(3*2)+(2*8)+(1*3)=59
59 % 10 = 9
So 1072-83-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H7NO/c1-5(8)6-3-2-4-7-6/h2-4,7H,1H3

1072-83-9 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A14593)  2-Acetylpyrrole, 98%   

  • 1072-83-9

  • 1g

  • 231.0CNY

  • Detail
  • Alfa Aesar

  • (A14593)  2-Acetylpyrrole, 98%   

  • 1072-83-9

  • 5g

  • 241.0CNY

  • Detail
  • Alfa Aesar

  • (A14593)  2-Acetylpyrrole, 98%   

  • 1072-83-9

  • 25g

  • 820.0CNY

  • Detail
  • Vetec

  • (V900549)  2-Acetylpyrrole  Vetec reagent grade, 98%

  • 1072-83-9

  • V900549-1G

  • 143.91CNY

  • Detail
  • Aldrich

  • (247359)  2-Acetylpyrrole  ReagentPlus®, 99%

  • 1072-83-9

  • 247359-5G

  • 308.88CNY

  • Detail
  • Aldrich

  • (247359)  2-Acetylpyrrole  ReagentPlus®, 99%

  • 1072-83-9

  • 247359-25G

  • 1,466.01CNY

  • Detail
  • Sigma-Aldrich

  • (30642)  2-Acetylpyrrole  analytical standard

  • 1072-83-9

  • 30642-100MG

  • 606.06CNY

  • Detail

1072-83-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-acetylpyrrole

1.2 Other means of identification

Product number -
Other names 2-Acetyl pyrrole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1072-83-9 SDS

1072-83-9Relevant articles and documents

-

Loader,Anderson

, p. 45 (1971)

-

-

Skell,Bean

, p. 4655,4659 (1962)

-

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

Kimura, Yukihiro,Yamamoto, Masataka,Tobita, Seiji,Shizuka, Haruo

, p. 459 - 465 (1997)

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

ünver, Halil,Biyikoglu, Mutluhan,Bulut, Adnan

, p. 8772 - 8774 (2013)

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 %).

-

Pommier,Lucas

, p. 139,142 (1973)

-

1,2-Dioximes in the Trofimov reaction

Zaitsev,Schmidt,Vasil'tsov,Mikhaleva,Petrova,Afonin,Zorina

, p. 34 - 41 (2006)

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.

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

Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae

supporting information, p. 23743 - 23749 (2021/10/14)

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.

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

Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.

, p. 5990 - 6007 (2021/08/24)

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.

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