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.

Odor Type

grape

Merck 

14,413

JECFA Number

2043

BRN 

386122

InChIKey

GTDQGKWDWVUKTI-UHFFFAOYSA-N

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 

Yes

HS Code 

29223990

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is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.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
• 2-Aminophenol
• 8-Bromo-3-methyl-xanthine
• (R)-1-Boc-3-Aminopiperidine
• o-Anisidine
• 1,2-Dimethoxybenzene
• 2-Bromobenzonitrile
• 3-Methoxysalicylaldehyde
• 1-Bromo-2-iodobenzene
• o-Phenetidine
• aminoacetophenon
• Anthranilic acid