2-Acetylpyrrole

HCID 14079CAS 1072-83-9
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(=O)c1ccc[nH]1
InChIKey
IGJQUJNPMOYEJY-UHFFFAOYSA-N
Molecular formula
C6H7NO
Average molar mass
109.13 g/mol
Monoisotopic mass
109.05276384

Overview

2-acetylpyrrole is a pyrrole carrying an acetyl substituent at the 2-position. It is a member of pyrroles, a methyl ketone and an aromatic ketone.

Names & identifiers

Preferred name
2-Acetylpyrrole
IUPAC
1-(1H-pyrrol-2-yl)ethanone
English name
2-Acetyl pyrrole
Molecular formula
C6H7NO
Molecular weight
109.13

Names & synonyms

2-ACETYLPYRROLE1072-83-91-(1H-Pyrrol-2-yl)ethanone1-(1H-Pyrrol-2-yl)ethan-1-one2-PyrrolylethanoneEthanone, 1-(1H-pyrrol-2-yl)-Methyl pyrrol-2-yl ketoneKetone, methyl pyrrol-2-ylMethyl 2-pyrrolyl ketone2-Acetyl-1H-pyrrole2-Pyrrolyl methyl ketone1-(2-Pyrrolyl)-1-ethanone
Show more names
ACETYL-2 PYRROLE1-(1H-PYRROL-2-YL)-ETHANONEEthanone,1-(1H-pyrrol-2-yl)-FEMA 3202(2-Pyrrolyl)ethanoneAcetopyrrole
FEMA No. 3202DTXSID00470849K28W7PM6NCHEBI:59981NSC-42861DTXCID8027084RefChem:462871214-016-2

Database identifiers

CAS
1072-83-9
PubChem CID
14079
DTXSID
DTXSID0047084
ChEMBL
CHEMBL1414126
ChEBI
CHEBI:59981
UNII
9K28W7PM6N
EC Number
214-016-2
Nikkaji
J80.142I

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
32.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
8

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
FragrancesFragrance Ingredient (Methyl 2-pyrrolyl ketone) -> IFRA transparency List
LogP · 2 items

0.93

0.93

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

Soluble in water and ether

Soluble (in ethanol)

Physicochemical properties

Melting point
88 · 88-93 °C (lit.)
Boiling point
220 °C · 220 °C (lit.)
Density
1.1143 · 1.1143 (rough estimate)
refractive index
1.504 · 1.5040 (estimate)
FEMA
3202 · 3202 | METHYL 2-PYRROLYL KETONE
FLAVIS Number
14.047 · 14.047 | 2-Acetylpyrrole

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.6% (37 of 1440) of reports.

Warning

H315 (97.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P280, P302+P352, P321, P332+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 1440 reports by companies from 12 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: Ethanone, 1-(1H-pyrrol-2-yl)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanone, 1-(1H-pyrrol-2-yl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (97.4%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
OB5970000
hs_code
29339990
risk_code
22-37/38-36/37/38

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 4 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationEthanone, 1-(1H-pyrrol-2-yl)-: ACTIVE
Applications · 6 items

Description2-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.

DescriptionMethyl 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.

OccurrenceReported 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.

Uses2-Acetylpyrrole has been used in the synthesis of 2-acetyl-1-pyrroline.

Useshepatoprotectant, organoleptic

General Description2-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.

Preparation methods

PreparationFrom pyrrole magnesium iodide and acetyl chloride; a volatile flavor component in roasted filberts

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

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

Related reactions

32 records
New reaction record

Linked notes

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