2'-Aminoacetophenone (HCID 11086)

概要

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is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.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

名称と識別子

優先名称: 2'-Aminoacetophenone
IUPAC: 1-(2-aminophenyl)ethanone
現地名: 2'-アミノアセトフェノン
英語名: 2-Aminoacetophenone
分子式: C8H9NO
分子量: 135.16

名称と別名

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

名称をさらに表示

2'-アミノアセトフェノン2-アセチルアニリンo-アミノアセトフェノン1-(2-アミノフェニル)エタノン2′-アミノアセトフェノンo-アミノアセトフェノン(2′-)2′‐アミノアセトフェノン2'-アミノアセトフェノン, 98%FEMA 39062-AMINO-1-PHENYLETHANONE1-(2-aminophenyl)-ethanone2’-amino-acetophenon1-(2-aminophenyl)-ethanon

2-acetylphenylamineDTXSID4052213NSC-882069Y77091BCDTXCID6030784FEMA NO. 3906CHEBI:91110RefChem:855192

データベース識別子

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

物性

構造計算による物性

XLogP: 1.6
極性表面積: 43.1 Å²
水素結合供与体数: 1
水素結合受容体数: 2
回転可能結合数: 1
重原子数: 10
形式電荷: 0
複雑度: 133

実験および物理化学的性質

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

物理化学的性質

融点: 20 °C · 20 °C
沸点: 85 · 85-90 °C0.5 mm Hg(lit.)
比重(密度): 1.112 g/mL · 1.112 g/mL at 25 °C(lit.)
屈折率: 20 · n20/D 1.614(lit.)
FEMA: 3906 · 3906 | 2-AMINOACETOPHENONE
闪点: 230 °F · >230 °F
貯蔵温度: 2 · 2-8°C
溶解性: ジクロロメタン（少量）、DMSO、メタノール（少量）
酸解離定数(Pka): 2.31 · 2.31±0.10(Predicted)
外見: 液体
色: 黄色から黄褐色
臭い (Odor): ブドウの甘い
由来生物: synthetic
においのタイプ: 葡萄
JECFA Number: 2043 · 2043
Merck: 14 · 14,413
BRN: 386122 · 386122
主な用途: フレーバーそして香料
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 データベース: 551 · 551-93-9(CAS DataBase Reference)
NISTの化学物質情報: 1 · Ethanone, 1-(2-aminophenyl)-(551-93-9)
EPAの化学物質情報: 1 · Ethanone, 1-(2-aminophenyl)- (551-93-9)

化学的性質 · 1 件

化学的特性2-Aminoacetophenone, also known as o-aminoacetophenone or 2-AA, is a yellow to yellow-brown liquid that 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.

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 4 件

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%)

安全と保護具

Disposal Methods · 2 件

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/

毒性情報

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Non-Human Toxicity Excerpts · 1 件

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.

安全データ

wgk: 3
tsca: TSCA listed
rtecs: AM5775000
hs_code: 29223990
risk_code: 36/37/38
消防法: 危-4-3-III
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36-24/25-37/39
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 10 - Combustible liquids
有毒物質データの: 551-93-9(Hazardous Substances Data)

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

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

用途と製造

Methods of ManufacturingPREPN OF O- ISOMERS

Use Classification · 2 件

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationEthanone, 1-(2-aminophenyl)-: ACTIVE

応用分野 · 4 件

用途有機合成用原料、香料材料。

天然物の起源Reported present in chestnut honey (>154 ppb)*; green tea and wine (0.7 to 12.8 μg/L).

使用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.

一般的な説明2′-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.

調製方法

製造方法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.

上流・下流製品情報

上流原料

メチルリチウムイサト酸無水物

下流製品

Ethyl 2,4-dimethylquinoline-3-carboxylate 2-(クロロメチル)-4-メチルキノリン-3-カルボン酸エチル塩酸塩 2-Chloro-4-methylquinoline-3-carbonitrile 2-(1H-ピロール-2-イル)-4-メチルキノリン 2-Amino-4-methyl-quinoline-3-carbonitrile 3-メチル-1H-インドール-2-カルボニトリル (2,4-Dimethylquinolin-3-yl)acetic acid hydrochloride 3-メチル-1H-インドール-2-カルボン酸エチル Methyl 2-(chloromethyl)-4-methylquinoline-3-carboxylate hydrochloride 3-メチル-1H-インダゾール-5-アミン 2-Ethyl-4-methylquinoline-3-carboxylic acid 2-アミノベンゼン酢酸

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上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

補足説明

定義ChEBI: 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.

2'-アミノアセトフェノン

基本情報

概要