| Identification | More | [Name]
2-Aminoacetophenone | [CAS]
551-93-9 | [Synonyms]
1-(2-AMINOPHENYL)ETHAN-1-ONE
1-(2-aminophenyl)-ethanone
2-AMINO-1-PHENYLETHANONE
2'-AMINOACETOPHENONE
2-AMINOACETOPHENONE
AMINOACETOPHENONE(2-)
ETHANONE, 1-(2-AMINOPHENYL)-
FEMA 3906
O-AMINOACETOPHENONE
O-AMINOPHENYL METHYL KETONE
1-(2-aminophenyl)-ethanon
1-Acetyl-2-aminobenzene
2’-amino-acetophenon
2-Acetylaniline
Acetophenone, 2'-amino-
o-acetylaniline
o-Aminoacetylbenzene
2'-AMINOACETOPHENONE 98+%
2'-AminoActophenone
2-Aminoacetophenone99% | [EINECS(EC#)]
209-002-8 | [Molecular Formula]
C8H9NO | [MDL Number]
MFCD00007717 | [Molecular Weight]
135.16 | [MOL File]
551-93-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to yellow-brown liquid | [Melting point ]
20 °C
| [Boiling point ]
85-90 °C0.5 mm Hg(lit.)
| [density ]
1.112 g/mL at 25 °C(lit.)
| [FEMA ]
3906 | [refractive index ]
n20/D 1.614(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
0-6°C | [solubility ]
Dichloromethane (Sparingly), DMSO, Methanol (Slightly) | [form ]
Liquid | [pka]
2.31±0.10(Predicted) | [color ]
Yellow to yellow-brown | [Odor]
grape sweet | [biological source]
synthetic | [Odor Type]
grape | [JECFA Number]
2043 | [Merck ]
14,413 | [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]
551-93-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3 | [RTECS ]
AM5775000 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29223990 | [Hazardous Substances Data]
551-93-9(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Chemical Properties]
2-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 Properties]
yellow to yellow-brown liquid | [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: 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[551-93-9] 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. This grape-like odor is often of diagnostic importance in detecting the growth of Pseudomonas aeruginosa in culture and in burn wounds. |
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