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Safety Information

247359

Sigma-Aldrich

2-Acetylpyrrole

ReagentPlus®, 99%

Synonym(s):

Methyl 2-pyrrolyl ketone

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About This Item

Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
1072-83-9
Molecular Weight:
109.13
Beilstein:
1882
EC Number:
214-016-2
MDL number:
MFCD00005220
UNSPSC Code:
12352100
PubChem Substance ID:
24854863
NACRES:
NA.22

Quality Level

100

product line

ReagentPlus®

Assay

99%

bp

220 °C (lit.)

mp

88-93 °C (lit.)

functional group

ketone

SMILES string

CC(=O)c1ccc[nH]1

InChI

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

InChI key

IGJQUJNPMOYEJY-UHFFFAOYSA-N

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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.

Application

2-Acetylpyrrole has been used in the synthesis of 2-acetyl-1-pyrroline.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

247359-VAR:
247359-25G:
247359-BULK:
247359-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ9219
SHBQ4206
SHBN7332
SHBM0251
MKBZ2265V

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Alkylation of 2-Acetylpyrrole and 1-alkyl-2-Acetylpyrroles Under Solid/Liquid Phase-Transfer Conditions.
Goldberg Y, et al.
Synthetic Communications, 21(4), 557-562 (1991)
Cooked rice aroma and 2-acetyl-1-pyrroline.
Buttery RG, et al.
Journal of Agricultural and Food Chemistry, 31(4), 823-826 (1983)
Wen-Yong Liu et al.
Journal of Asian natural products research, 5(3), 159-163 (2003-08-23)
Three pyrrole alkaloids were isolated from Bolbostemma paniculatum. Their structures were elucidated as 4-(2-formyl-5-methoxymethylpyrrol-1-yl)butyric acid methyl ester (1), 2-(2-formyl-5-methoxymethylpyrrol-1-yl)-3-phenylpropionic acid methyl ester (2) and alpha-methyl pyrrole ketone (3) by spectroscopic techniques. Among them, 1 and 2 are new compounds.
Jin Ho Lee et al.
The Journal of organic chemistry, 78(3), 1283-1288 (2013-01-08)
A new synthetic route to indolizines with various substituents on the pyridine moiety was developed by utilizing a facile cycloaromatization of 2-acetylpyrrole derivatives. Without isolation, the resulting intermediates were allowed to react with various electrophiles to afford a range of
G C Yen et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 24(12), 1303-1308 (1986-12-01)
Three 2-substituted pyrroles (2-acetylpyrrole, pyrrole-2-carboxaldehyde and pyrrole-2-carboxylic acid), which are products of the Maillard browning reaction, were reacted with nitrite in buffer solution (pH 3) at 50 degrees C for 24 hr. The reaction mixtures were extracted with methylene chloride
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