Grundinformationen
- Standard-SMILES
CC(=O)c1ccccc1N- InChIKey
GTDQGKWDWVUKTI-UHFFFAOYSA-N- Summenformel
- C8H9NO
- Durchschnittliche Molmasse
- 135,16 g/mol
- Monoisotopische Masse
- 135,06841391
Überblick
O-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is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group. It has a role as a bacterial metabolite. It is a member of acetophenones and a substituted aniline.
Namen und Bezeichner
- Bevorzugter Name
- 2'-Aminoacetophenone
- IUPAC
- 1-(2-aminophenyl)ethanone
- Lokaler Name
- 2'-Aminoacetophenon
- Englischer Name
- 2-Aminoacetophenone
- Summenformel
- C8H9NO
- Molmasse
- 135.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
27941-88-4、551-93-9- PubChem CID
- 11086
- DTXSID
DTXSID4052213- ChEMBL
CHEMBL2251601- ChEBI
CHEBI:91110- UNII
- 69Y77091BC
- EC Number
- 209-002-8
- Nikkaji
- J2.651D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 43,1 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 133
Experimentelle und physikochemische Eigenschaften
Color/Form
YELLOW OILY LIQUID
YELLOW CRYSTALS
Solubility
PRACTICALLY INSOL IN WATER; SOL IN ALC
SOL IN ETHER
Soluble in fats, acetone; Very slightly soluble in water
Soluble (in ethanol)
Boiling Point
BP 250-252 °C @ 760 MM HG (SOME DECOMP)
85.00 to 90.00 °C. @ 0.50 mm Hg
85-90 °C (0.5 mm Hg)
Melting Point
20 °C
20 °C
Refractive Index
INDEX OF REFRACTION: 1.6160 @ 20 °C/D; MAX ABSORPTION (ALC): 226 NM (LOG E= 4.32), 254 NM (LOG E= 3.75), 359 NM (LOG E= 3.64)
1.612-1.619
Physikochemische Eigenschaften
- Schmelzpunkt
- 20 °C · 20 °C
- Siedepunkt
- 85 · 85-90 °C0.5 mm Hg(lit.)
- Dichte
- 1.112 g/mL · 1.112 g/mL at 25 °C(lit.)
- Brechungsindex
- 20 · n20/D 1.614(lit.)
- FEMA
- 3906 · 3906 | 2-AMINOACETOPHENONE
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Dichloromethane (Sparingly), DMSO, Methanol (Slightly)
- pka
- 2.31 · 2.31±0.10(Predicted)
- Aggregatzustand
- Liquid
- Farbe
- Yellow to yellow-brown
- Geruch (Odor)
- grape sweet, Heavy-sweet, somewhat animal-floral odor of considerable tenacity, faintly reminiscent of tobacco leaf odor.
- Biologische Quelle
- synthetic
- Geruchsart
- grape
- JECFA Number
- 2043 · 2043
- Merck
- 14 · 14,413
- BRN
- 386122 · 386122
- Major Application
- flavors and fragrances
- InChI
- 1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3
- InChIKey
- GTDQGKWDWVUKTI-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccccc1N
- LogP
- 1.63 · 1.63
- CAS Datenbank
- 551 · 551-93-9(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · Ethanone, 1-(2-aminophenyl)-(551-93-9)
- EPA chemische Informationen
- 1 · Ethanone, 1-(2-aminophenyl)- (551-93-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 56.9% (78 of 137) of all reports.
Warning
H302 (13.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 137 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Ethanone, 1-(2-aminophenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 15-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20816
Ethanone, 1-(2-aminophenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Sicherheit und Schutzausrüstung
Disposal Methods
The following wastewater treatment technologies have been investigated for acetophenone: concentration process: activated carbon. /Acetophenone/
The following wastewater treatment technologies have been investigated for acetophenone: concentration process: resin adsorption. /Acetophenone/
Toxikologische Informationen
Non-Human Toxicity Excerpts
Methyl anthranilate is an effective bird repellent at concentrations of 1.0% (g/g). Ortho-aminoacetophenone has an odor similar to that of methyl anthranilate and is chemically (structurally) similar. Coincidentally, ortho-aminoacetophenone is present in the scent gland secretions of mustelid species that prey on birds. For these reasons, ... the bird repellency of this material and 3 isomers to European starlings (Sturnus vulgaris) /were tested/. Ortho-aminoacetophenone was repellent at concentrations 0.01% in both choice and no-choice feeding tests. The other structural isomers (meta-,para-, alpha-) were less effective. Chemically, the results suggest that hydrogen-bonded ring structure formation and basicity predict bird repellent activity.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29223990
- RTECS-Nr.
- AM5775000
- risk_code
- 36/37/38
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-24/25-37/39
- Speicherklasse
- 10 - Combustible liquids
- Giftige Stoffe Daten
- 551-93-9(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
YIELDS 2-CARBOXAMIDO-4-METHYLQUINAZOLINE, 2-HYDROXYMETHYL-4-METHYLQUINAZOLINE, & 4-METHYLQUINAZOLINE IN PSEUDOMONAS. /FROM TABLE/
2-AMINO-3-HYDROXYACETOPHENONE WAS ISOLATED FROM URINE OF RATS GIVEN 15 MG 2-AMINOACETOPHENONE/KG/DAY FOR 4 DAYS & FROM THE SUPERNATANT OF CULTURES OF RAT LIVER MICROSOMES INCUBATED WITH 2-AMINOACETOPHENONE FOR 2 HR AT 37 °C.
IN CELL-FREE EXTRACTS OF BACILLUS SUBTILIS, 2'-AMINOACETOPHENONE WAS UTILIZED AS RAPIDLY AS AMINOACETONE.
Verwendung und Herstellung
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Anwendungen
OccurrenceReported present in chestnut honey (>154 ppb)*; green tea and wine (0.7 to 12.8 μg/L).
Verwenden2′-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.
Darstellung
synthetischeSynthesis 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
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.
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