Basic information
- Standard SMILES
CC(=O)c1ccccc1N- InChIKey
GTDQGKWDWVUKTI-UHFFFAOYSA-N- Molecular formula
- C8H9NO
- Average molar mass
- 135.16 g/mol
- Monoisotopic mass
- 135.06841391
Overview
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is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.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.
Names & identifiers
- Preferred name
- 2'-Aminoacetophenone
- IUPAC
- 1-(2-aminophenyl)ethanone
- English name
- 2-Aminoacetophenone
- Molecular formula
- C8H9NO
- Molecular weight
- 135.16
Names & synonyms
2'-Aminoacetophenone551-93-91-(2-Aminophenyl)ethanone2-AcetylanilineO-AMINOACETOPHENONEo-Acetylaniline1-(2-Aminophenyl)Ethan-1-Oneo-Aminoacetylbenzene1-Acetyl-2-aminobenzeneAcetophenone, 2'-amino-Ethanone, 1-(2-aminophenyl)-ortho-aminoacetophenone
Show more names
FEMA 39062-AMINO-1-PHENYLETHANONE1-(2-aminophenyl)-ethanone2’-amino-acetophenon1-(2-aminophenyl)-ethanon
2-acetylphenylamineDTXSID4052213NSC-882069Y77091BCDTXCID6030784FEMA NO. 3906CHEBI:91110RefChem:855192
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 43.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 133
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP1.63
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.115-1.121
Flavoring AgentsEU Flavoring substances
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
Vapor Pressure0.00989 [mmHg]
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
Physicochemical properties
- Melting point
- 20 °C · 20 °C
- Boiling point
- 85 · 85-90 °C0.5 mm Hg(lit.)
- Density
- 1.112 g/mL · 1.112 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.614(lit.)
- FEMA
- 3906 · 3906 | 2-AMINOACETOPHENONE
- FLAVIS Number
- 11.008 · 11.008 | 2-Aminoacetophenone
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Dichloromethane (Sparingly), DMSO, Methanol (Slightly)
- pka
- 2.31 · 2.31±0.10(Predicted)
- form
- Liquid
- color
- Yellow to yellow-brown
- Odor
- grape sweet, Heavy-sweet, somewhat animal-floral odor of considerable tenacity, faintly reminiscent of tobacco leaf odor.
- biological source
- synthetic
- Odor Type
- 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 DataBase Reference
- 551 · 551-93-9(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 2 · 2'-AMINOACETOPHENONE
- FDA UNII
- 69 Y77091BC · 69Y77091BC
- NIST Chemistry Reference
- 1 · Ethanone, 1-(2-aminophenyl)-(551-93-9)
- EPA Substance Registry System
- 1 · Ethanone, 1-(2-aminophenyl)- (551-93-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-24/25-37/39
- WGK Germany
- 3 · 3
- RTECS
- 5775000 · AM5775000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29223990 · 29223990
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 551 · 551-93-9(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
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.
Hazard information
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
Hazards SummaryAn irritant; May induce methemoglobinemia; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (13.9%)
Safety & protection
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/
Toxicology
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
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.
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AM5775000
- hs_code
- 29223990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-24/25-37/39
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 551-93-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
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.
Cellular LocationsCytoplasm
Uses & manufacturing
Methods of ManufacturingPREPN OF O- ISOMERS
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationEthanone, 1-(2-aminophenyl)-: ACTIVE
Applications
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.
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.
Preparation methods
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
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.
Related reactions
65 records
Linked notes
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