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2'-Aminoacetophenone

HCID 11086
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
27941-88-4
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is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.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 propertiesFilling in

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 · 2 items

YELLOW OILY LIQUID

YELLOW CRYSTALS

Solubility · 4 items

PRACTICALLY INSOL IN WATER; SOL IN ALC

SOL IN ETHER

Soluble in fats, acetone; Very slightly soluble in water

Soluble (in ethanol)

Boiling Point · 3 items

BP 250-252 °C @ 760 MM HG (SOME DECOMP)

85.00 to 90.00 °C. @ 0.50 mm Hg

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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 · 4 items

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 · 2 items

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/

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

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 · 2 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationEthanone, 1-(2-aminophenyl)-: ACTIVE
Applications · 3 items

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

Related reactions

65 records
New reaction record
HRID 52511 reaction equation
HRID 52511As reactantuspto-grants-1997_04
HRID 76995 reaction equation
HRID 76995As reactantuspto-grants-2014_09
HRID 117657 reaction equation
HRID 117657As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 161833 reaction equation
HRID 161833As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 179418 reaction equation
HRID 179418As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 192260 reaction equation
HRID 192260As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 298372 reaction equation
HRID 298372As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 364925 reaction equation
HRID 364925As reactantuspto-grants-1986_08
Page 1 of 9

Compound notes

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85-90 °C (0.5 mm Hg)

Melting Point · 2 items

20 °C

20 °C

Vapor Pressure0.00989 [mmHg]
Refractive Index · 2 items

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

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Non-Human Toxicity Excerpts · 1 item

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)

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

MethyllithiumIsatoic Anhydride

Downstream products

Ethyl 2,4-dimethylquinoline-3-carboxylateEthyl 2-(chloromethyl)-4-methylquinoline-3-carboxylate hydrochloride2-Chloro-4-methylquinoline-3-carbonitrile4-Methyl-2-(1H-pyrrol-2-yl)quinoline2-Amino-4-methyl-quinoline-3-carbonitrile1H-Indole-2-carbonitrile,3-methyl-(2,4-Dimethylquinolin-3-yl)acetic acid hydrochlorideEthyl3-methyl-2-indolecarboxylateMethyl 2-(chloromethyl)-4-methylquinoline-3-carboxylate hydrochloride3-Methyl-1H-indazol-5-amine2-Ethyl-4-methylquinoline-3-carboxylic acid2-Aminophenylacetic acid9-Methylacridine2,4-Dimethylquinoline-3-carboxylic acid1-(2,4-Dimethylquinolin-3-yl)ethanone hydrochloride3-Chloro-2-(chloromethyl)-4-methylquinoline hydrochloride1-(2-Aminophenyl)-3-(2-chlorophenyl)propan-1-one2-(3,4-Dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one3-Quinolinecarboxylic acid, 2-ethyl-4-methyl-4-Chloro-2-(p-tolyl)quinoline-1(2H)-carbaldehyde2-(3-Fluoro-phenyl)-2,3-dihydro-1H-quinolin-4-one

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.