ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic alcohol 2-Aminoacetophenone

2-Aminoacetophenone

2-Aminoacetophenone Basic information
Product Name:2-Aminoacetophenone
Synonyms:1-(2-aminophenyl)-ethanon;1-Acetyl-2-aminobenzene;2’-amino-acetophenon;2-Acetylaniline;Acetophenone, 2'-amino-;o-acetylaniline;o-Aminoacetylbenzene;2-AMINO-1-PHENYLETHANONE
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
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 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.
Chemical Propertiesyellow to yellow-brown liquid
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: An aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.
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.{9] It is also reported to be responsible for the grape-like odor in culture media growing Pseudomonas aeruginosa.
2-Aminoacetophenone Preparation Products And Raw materials
Preparation Products2-ETHYL-4-METHYLQUINOLINE-3-CARBOXYLIC ACID-->2,4-DIMETHYLQUINOLINE-3-CARBOXYLIC ACID-->ETHYL 2-(CHLOROMETHYL)-4-METHYLQUINOLINE-3-CARBOXYLATE HYDROCHLORIDE-->METHYL 2-(CHLOROMETHYL)-4-METHYLQUINOLINE-3-CARBOXYLATE HYDROCHLORIDE-->(2,4-DIMETHYLQUINOLIN-3-YL)ACETIC ACID HYDROCHLORIDE-->1H-Indole-2-carbonitrile,3-methyl--->2-AMINO-4-METHYL-QUINOLINE-3-CARBONITRILE-->ETHYL3-METHYL-2-INDOLECARBOXYLATE-->3-METHYL-1H-INDAZOL-5-AMINE-->2-CHLORO-4-METHYLQUINOLINE-3-CARBONITRILE-->2-AMINOPHENYLACETIC ACID-->1-(2,4-DIMETHYLQUINOLIN-3-YL)ETHANONE HYDROCHLORIDE-->ETHYL 2,4-DIMETHYLQUINOLINE-3-CARBOXYLATE-->9-METHYLACRIDINE-->4-METHYL-2-(1H-PYRROL-2-YL)QUINOLINE-->3-CHLORO-2-(CHLOROMETHYL)-4-METHYLQUINOLINE HYDROCHLORIDE-->1-(2-Aminophenyl)-3-(2-chlorophenyl)propan-1-one-->2-(3,4-DIMETHOXYPHENYL)-2,3-DIHYDROQUINOLIN-4(1H)-ONE-->3-Quinolinecarboxylic acid, 2-ethyl-4-methyl--->4-Chloro-2-(p-tolyl)quinoline-1(2H)-carbaldehyde-->2-(3-Fluoro-phenyl)-2,3-dihydro-1H-quinolin-4-one
OIL BLUE N Methyl anthranilate REACTIVE BLUE 4 ACID VIOLET 34 Solvent Green 3 aminoacetophenon 3-Nitroacetophenone ACID BLUE 80 2-Aminoacetophenone Acetophenone L-PICEIN 4'-Hydroxyacetophenone 2-Aminobenzaldehyde Disperse Blue 3 2-Aminophenol 2'-Hydroxyacetophenone Anthranilic acid ACID BLUE 40
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