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247359

Sigma-Aldrich

2-Acetylpyrrole

ReagentPlus®, 99%

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

Quality Level

100

product line

ReagentPlus®

Assay

99%

bp

220 °C (lit.)

mp

88-93 °C (lit.)

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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1 of 4

This Item
W320218395137128740
2-Acetylpyrrole ReagentPlus®, 99%

Sigma-Aldrich

247359

2-Acetylpyrrole

Methyl 2-pyrrolyl ketone ≥98%, FG

Sigma-Aldrich

W320218

Methyl 2-pyrrolyl ketone

2-(Trichloroacetyl)pyrrole 99%

Sigma-Aldrich

395137

2-(Trichloroacetyl)pyrrole

2-Hydroxy-6-methylpyridine 97%

Sigma-Aldrich

128740

2-Hydroxy-6-methylpyridine

bp

220 °C (lit.)

bp

220 °C (lit.)

bp

-

bp

-

mp

88-93 °C (lit.)

mp

88-93 °C (lit.)

mp

72-74 °C (lit.)

mp

157-159 °C (lit.)

product line

ReagentPlus®

product line

-

product line

-

product line

-

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 Sigma-Aldrich Co. LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Cooked rice aroma and 2-acetyl-1-pyrroline.
Buttery RG, et al.
Journal of Agricultural and Food Chemistry, 31(4), 823-826 (1983)
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)
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
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.
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Protocols

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-Cymene; 2,5-Dimethylpyrrole; Acetoin, ≥96%, FCC, FG; 2,5-Dimethylpyrazine; 2,6-Dimethylpyrazine; 2-Ethylpyrazine, ≥98%, FG; 2,3-Dimethylpyrazine; 4-Heptanone; 3-Ethylpyridine; 2,3,5-Trimethylpyrazine; Furfural; Pyrrole; Furfuryl acetate; Linalool; Linalyl acetate; 5-Methylfurfural; γ-Butyrolactone; 2-Acetyl-1-methylpyrrole; Furfuryl alcohol; 2-Acetylpyrrole; Pyrrole-2-carboxaldehyde

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