932-16-1

Basic information

• Product Name: 2-Acetyl-1-methylpyrrole
• Synonyms: FEMA 3184;FEMA NUMBER 3184;METHYL 1-METHYL-2-PYRROLYL KETONE;2-ACETYL-N-METHYLPYRROLE;2-ACETYL-1-METHYLPYRROLE;1-METHYL-2-ACETYLPYRROLE;N-METHYL-2-ACETYLPYRROLE;1-(1-methyl-1h-pyrrol-2-yl)-ethanon
• CAS NO: 932-16-1
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• EINECS: 213-247-6
• Product Categories: Flavor;A-B;Alphabetical Listings;Flavors and Fragrances;Building Blocks;Heterocyclic Building Blocks;Pyrroles;ketone
• Mol File: 932-16-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 200-202 °C(lit.)
• Flash Point: 155 °F
• Appearance: /
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.292mmHg at 25°C
• Refractive Index: n20/D 1.542(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -7.46±0.70(Predicted)
• BRN: 111887
• CAS DataBase Reference: 2-Acetyl-1-methylpyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetyl-1-methylpyrrole(932-16-1)
• EPA Substance Registry System: 2-Acetyl-1-methylpyrrole(932-16-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 932-16-1(Hazardous Substances Data)

Usage

Description

May be prepared from Af-methyl pyrrole and Grignard reagent; by acetylation of 1-methyl-pyrrole.

Occurrence

Reported found as a component in coffee aroma, asparagus, crispbread, cooked beef, black tea, okra and clam.

Uses

2-Acetyl-1-methylpyrrole was employed as model pyrrole to investigate the antioxidative activity of nonenzymatic browning reactions. It was employed as catalyst for the sulfonylation of spectinomycin.

Definition

ChEBI: A pyrrole carrying methyl and acetyl substituent at the 1- and 2-positions respectively.

Preparation

From N-methyl pyrrole and Grignard reagent; by acetylation of 1-methyl-pyrrole.

Aroma threshold values

Detection: 100 ppb

Synthesis Reference(s)

Synthetic Communications, 21, p. 557, 1991 DOI: 10.1080/00397919108016783

General Description

Reduction of 2-acetyl-1-methylpyrrole with sodium borohydride has been investigated.

InChI:InChI=1/C7H9NO/c1-6(9)7-4-3-5-8(7)2/h3-5H,1-2H3

Upstream product

• 96-54-8 N-Methylpyrrole 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 109-63-7 trifluoroborane diethyl ether 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 60-29-7 diethyl ether 
• 75-36-5 acetyl chloride 
• 90345-20-3 1-(1-methyl-1H-pyrrol-2-yl)ethanone oxime 
• 74-86-2 acetylene 
• 58569-87-2 N-(1-chloroethylidene)-N-methylmethanaminium chloride 
• 2540-06-9 1-methyl-2-vinyl-1H-pyrrole 
• 18519-25-0 1-methyl-1H-pyrrol-2-yl thiocyanate 
• 1696-20-4 4-acetylmorpholine 
• 73671-59-7 1-methyl-2-methylthiopyrrole 

Downstream Products

• 56423-58-6 2-(1-hydroxyethyl)-1-methylpyrrole 
• 13138-78-8 1-methyl-4-nitro-pyrrol-2-carboxylic acid 
• 1131890-54-4 N-(1-(1-methyl-1H-pyrrol-2-yl)ethylidene)aniline 
• 93304-03-1 1-(1-methyl-1H-pyrrole-2-yl)-2-phenyl-ethanone 
• 23694-02-2 2-chloro-1-(1-methyl-1H-pyrrol-2-yl)ethanone 
• 108213-07-6 1,1'-(1-methyl-1H-pyrrole-2,4-diyl)bis(ethanone) 
• 21898-43-1 2-(1-methyl-1H-pyrrol-2-yl)-2-oxoacetic acid 

Relevant articles and documents

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Electronic Asymmetry of an Annelated Pyridyl-Mesoionic Carbene Scaffold: Application in Pd(II)-Catalyzed Wacker-Type Oxidation of Olefins

The two donor modules of an annelated pyridyl-mesoionic carbene ligand (aPmic) have different σ- and π-bonding characteristics leading to its electronic asymmetry. A Pd(II) complex 1 featuring aPmic catalyzes the oxidation of a wide range of terminal olefins to the corresponding methyl ketones in good to excellent yields in acetonitrile. The catalytic reaction is proposed to proceed via syn-peroxypalladation and a subsequent rate-limiting 1,2-hydride shift, which is supported by kinetic studies. The electronic asymmetry of aPmic renders a well-defined coordination sphere at Pd. The favored arrangement of reactants on the metal center features an olefin trans to the pyridyl module and a tbutylperoxide trans to the carbene. This arrangement gains added stability by the π-delocalization paved by the compatible orbitals on Pd, the pyridyl module, and the olefin that is perpendicular to the Pd(aPmic) plane. The π-interactions are absent in an alternate arrangement wherein the olefin is trans to the carbene. Density functional theory studies reveal the matching orbital overlaps responsible for the preferred arrangement over the other. This work provides an orbital description for the electronic asymmetry of aPmic.

Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.