2-Aminoacetophenone Chemical Properties

Melting point:

20 °C

Boiling point:

85-90 °C0.5 mm Hg(lit.)

Density 

1.112 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.614(lit.)

FEMA 

3906 | 2-AMINOACETOPHENONE

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Dichloromethane (Sparingly), DMSO, Methanol (Slightly)

pka

2.31±0.10(Predicted)

form 

Liquid

color 

Yellow to yellow-brown

Odor

grape sweet, Heavy-sweet, somewhat animal-floral odor of considerable tenacity, faintly reminiscent of tobacco leaf odor.

biological source

synthetic

Odor Type

grape

JECFA Number

2043

Merck 

14,413

BRN 

386122

Major Application

flavors and fragrances

InChI

1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3

InChIKey

GTDQGKWDWVUKTI-UHFFFAOYSA-N

SMILES

CC(=O)c1ccccc1N

LogP

1.63

CAS DataBase Reference

551-93-9(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(2-aminophenyl)-(551-93-9)

EPA Substance Registry System

Ethanone, 1-(2-aminophenyl)- (551-93-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25-37/39

WGK Germany 

3

RTECS 

AM5775000

Hazard Note 

Irritant

TSCA 

TSCA listed

HS Code 

29223990

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

Hazardous Substances Data

551-93-9(Hazardous Substances Data)

MSDS

• Language:English Provider:2-Aminoacetophenone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Aminoacetophenone Usage And Synthesis

Chemical Properties

2-Aminoacetophenone, also known as o-aminoacetophenone or 2-AA, is a yellow to yellow-brown liquid that has a grape-like odor. Aminoacetophenone is a pheromone produced by virgin honeybee queens and released in feces. The pheromone repels and is used to terminate agonistic interactions between queens and workers. A grape-like odor of 2-aminoacetophenone is of diagnostic importance in detecting the growth of Pseudomonas aeruginosa in culture and in burn wounds.

Occurrence

Reported present in chestnut honey (>154 ppb)*; green tea and wine (0.7 to 12.8 μg/L).

Uses

2′-Aminoacetophenone may be used as an analytical standard for the determination of the analyte in livestock particulate matter, and grape-derived beverages by gas chromatography-mass spectrometry-olfactometry (GC-MS-O) and GC-MS, respectively.

Definition

ChEBI: 2-Aminoacetophenone is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.

Preparation

Synthesis of 2-Aminoacetophenone by reaction of methyl lithium with Isatoic anhydride in an anhydrous or nearly anhydrous solvent at a reaction temperature of -50°C or less.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 4561, 1954 DOI: 10.1021/ja01647a016
Journal of Heterocyclic Chemistry, 24, p. 297, 1987 DOI: 10.1002/jhet.5570240201
Journal of the American Chemical Society, 105, p. 943, 1983 DOI: 10.1021/ja00342a050
The Journal of Organic Chemistry, 45, p. 4926, 1980 DOI: 10.1021/jo01312a021
The Journal of Organic Chemistry, 22, p. 358, 1957 DOI: 10.1021/jo01355a002

General Description

2′-Aminoacetophenone is one of the key volatile flavor components of masa corn flour products. It is also reported to be responsible for the grape-like odor in culture media growing Pseudomonas aeruginosa.

2-Aminoacetophenone(551-93-9)Related Product Information

• Methyl anthranilate
• Acetophenone
• 4'-Hydroxyacetophenone
• L-PICEIN
• 3-Nitroacetophenone
• 2'-Hydroxyacetophenone
• 2-Aminobenzaldehyde
• 8-Bromo-3-methyl-xanthine
• (R)-1-Boc-3-Aminopiperidine
• o-Anisidine
• 1,2-Dimethoxybenzene
• 2-Bromobenzonitrile
• 1-Bromo-2-iodobenzene
• o-Phenetidine
• 2-Aminophenol
• 3-Methoxysalicylaldehyde
• aminoacetophenon
• Anthranilic acid