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2-Aminoacetophenone

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CAS:551-93-9
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  • 2024-01-08
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2-Aminoacetophenone Basic information
Product Name:2-Aminoacetophenone
Synonyms:1-(2-aminophenyl)-ethanon;2’-amino-acetophenon;Acetophenone, 2'-amino-;o-acetylaniline;o-Aminoacetylbenzene;2-AMINOACETOPHENONE;1-(2-aminophenyl)-ethanone;AMINOACETOPHENONE(2-)
CAS:551-93-9
MF:C8H9NO
MW:135.16
EINECS:209-002-8
Product Categories:Aromatic Acetophenones & Derivatives (substituted);pharmaceutical intermediates;Amines and Anilines;Carbonyl Compounds;J's;551-93-9;bc0001;john's
Mol File:551-93-9.mol
2-Aminoacetophenone Structure
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.)
FEMA 3906 | 2-AMINOACETOPHENONE
refractive index n20/D 1.614(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility Dichloromethane (Sparingly), DMSO, Methanol (Slightly)
form Liquid
pka2.31±0.10(Predicted)
color Yellow to yellow-brown
Odorgrape sweet
Odor Typegrape
Merck 14,413
JECFA Number2043
BRN 386122
InChIKeyGTDQGKWDWVUKTI-UHFFFAOYSA-N
LogP1.63
CAS DataBase Reference551-93-9(CAS DataBase Reference)
NIST Chemistry ReferenceEthanone, 1-(2-aminophenyl)-(551-93-9)
EPA Substance Registry SystemEthanone, 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 Data551-93-9(Hazardous Substances Data)
MSDS Information
ProviderLanguage
2-Aminoacetophenone English
SigmaAldrich English
ACROS English
ALFA English
2-Aminoacetophenone Usage And Synthesis
Chemical Properties2-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.
OccurrenceReported present in chestnut honey (>154 ppb)*; green tea and wine (0.7 to 12.8 μg/L).
Uses2′-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.
DefinitionChEBI: 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.
PreparationSynthesis 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 Description2′-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.
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