551-93-9

Name	2-Aminoacetophenone
CAS	551-93-9
EINECS(EC#)	209-002-8
Molecular Formula	C8H9NO
MDL Number	MFCD00007717
Molecular Weight	135.16
MOL File	551-93-9.mol

Chemical Properties

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
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

Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
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 . less more
WGK Germany	3
RTECS	AM5775000
Hazard Note	Irritant
TSCA	Yes
HS Code	29223990
Hazardous Substances Data	551-93-9(Hazardous Substances Data)

Raw materials And Preparation Products

Hazard Information

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ChEBI: An aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.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

Material Safety Data Sheet(MSDS)

Spectrum Detail

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