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2'-アセトナフトン

2-Acetylnaphthalene

HCID 7122
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
1333-52-4
標準SMILES
CC(=O)c1ccc2ccccc2c1
InChIKey
XSAYZAUNJMRRIR-UHFFFAOYSA-N
分子式
C12H10O
平均分子量
170.21 g/mol
単同位体質量
170.07316494

概要

2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.

名称と識別子

優先名称
2-Acetylnaphthalene
IUPAC
1-naphthalen-2-ylethanone
現地名
2'-アセトナフトン
英語名
2-Acetonaphthone
分子式
C12H10O
分子量
170.21

名称と別名

2-Acetylnaphthalene2-Acetonaphthone93-08-32'-Acetonaphthone1-(naphthalen-2-yl)ethanoneMethyl 2-naphthyl ketoneEthanone, 1-(2-naphthalenyl)-1-(2-Naphthyl)ethanone2-Naphthyl methyl ketoneAcetonaphthoneMethyl beta-naphthyl ketoneOranger cyrstals
名称をさらに表示
2'-アセトナフトンメチルナフチルケトン2-アセチルナフタレンβ-アセトナフトン1-(2-ナフタレニル)エタノン1-(2-ナフチル)エタノン2-アセトナフトンメチルβ-ナフチルケトンメチル2-ナフチルケトンメチル(2-ナフチル)ケトン(2-ナフチル)(メチル)ケトン2-ナフチル(メチル)ケトンメチル β-ナフチルケトン2′-アセトナフトン2′‐アセトナフトン2-(ナフタレン-2-イル)-1-オキソエタニド2-(ナフタレン-1-イル)-1-オキソエタニド1-ナフチルメチルケトン2-ナフチルメチルケトンORANGE IIMETHYL NAPHTHYL KETONEMethyl β-naphthyl ketoneORANGE 2ACID ORANGE IIFEMA 27232-Acetonaphthone99%
beta-AcetonaphthoneCetone D1-(2-NAPHTHALENYL)ETHANONEbeta-AcetonaphthaleneOranger crystalsKetone, methyl 2-naphthylbeta-Naphthyl methyl ketone1-(naphthalen-2-yl)ethan-1-one

データベース識別子

CAS
1333-52-4、93-08-3
PubChem CID
7122
DTXSID
DTXSID2041389
ChEMBL
CHEMBL3183700
ChEBI
CHEBI:52364
UNII
21D49LOP2T
EC Number
202-216-2、215-594-9
Nikkaji
J2.840A

物性

構造計算による物性補完中

XLogP
3.2
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
1
重原子数
13
形式電荷
0
複雑度
197

実験および物理化学的性質

Chemical ClassesOther Classes -> Naphthalenes
PolymersPolycyclic aromatic compound
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Fragrances · 2 件

Fragrance Ingredient (1-(Naphthyl)ethan-1-one) -> IFRA transparency List

Fragrance Ingredient (Methyl beta-naphthyl ketone) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 3 件

0.272 mg/mL at 25 °C

insoluble in water; soluble in organic solvents, oils

soluble (in ethanol)

Boiling Point · 2 件

300.00 to 301.00 °C. @ 760.00 mm Hg

300 °C

Melting Point56 °C
Physical Description · 4 件

Liquid; CBI

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 67.4% (1321 of 1959) of all reports.

Warning

H302 (11.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1959 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 5 件

Chemical: Ethanone, 1-(2-naphthalenyl)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanone, 1-(2-naphthalenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-(2-naphthalenyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 16-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11282

2-Acetylnaphthalene: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Naphthalene.
Hazard Classes and Categories · 2 件

Acute Tox. 4 (11.3%)

Acute Tox. 4 (100%)

毒性情報

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

化学と産業

薬理情報

Cellular LocationsMembrane

用途と製造

UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 7,000,000 - <8,500,000 lb
Consumer UsesFragrance
Industry UsesFragrance
IFRA Fragrance Standards · 6 件

Methyl beta-naphthyl ketone

2-Acetonaphthone; β-Acetylnaphthalene; Cetone d; Ethanone, 1-(2-naphthalenyl); β-Methyl naphthyl ketone; β-Naphthyl methyl ketone; Oranger crystals

IFRA_STD_095.pdf

49

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

Household ProductsInformation on 27 consumer products that contain 2-Acetylnaphthalene
 in the following categories is provided:
Use Classification · 6 件

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 件

All Other Chemical Product and Preparation Manufacturing

Ethanone, 1-(2-naphthalenyl)-: ACTIVE

Restriction Limits in the Finished Product (%)

関連反応

56 件
反応記録を作成
HRID 65214 の反応式
HRID 65214反応物としてuspto-grants-1986_09
HRID 116992 の反応式
HRID 116992反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 130297 の反応式
HRID 130297反応物としてuspto-grants-2008_06
HRID 130298 の反応式
HRID 130298反応物としてuspto-grants-2008_06
HRID 248231 の反応式
HRID 248231反応物としてuspto-grants-1993_05
HRID 322597 の反応式
HRID 322597反応物としてuspto-grants-2001_04
HRID 324754 の反応式
HRID 324754反応物としてuspto-grants-2001_04
HRID 324763 の反応式
HRID 324763反応物としてuspto-grants-2001_04
1 / 7 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
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White powder; [Alfa Aesar MSDS]

Solid

white or nearly white crystalline solid with a floral, orange blossom, neroli odour

物理化学的性質

融点
52 · 52-56 °C (lit.)
沸点
300 · 300-301 °C (lit.)
比重(密度)
1.12 g/mL · 1.12 g/mL at 25 °C(lit.)
蒸気圧
0.12 Pa · 0.12Pa at 25℃
FEMA
2723 · 2723 | METHYL BETA-NAPHTHYL KETONE
屈折率
20 · n20/D 1.628(lit.)
闪点
230 °F · >230 °F
貯蔵温度
Sealed in dry,Room Temperature
溶解性
0.272 g/リットル · 0.272g/リットル
外見
微結晶性粉末およびチャンク
酸解離定数(Pka)
0 · 0[at 20 ℃]
色
白い
臭い (Odor)
オレンジの花の匂い
においのタイプ
花柄
由来生物
synthetic
水溶解度
不溶性
JECFA Number
811 · 811
BRN
774965 · 774965
化粧品成分の機能
香料香料
InChI
1S/C12H10O/c1-9(13)11-7-6-10-4-2-3-5-12(10)8-11/h2-8H,1H3
InChIKey
XSAYZAUNJMRRIR-UHFFFAOYSA-N
SMILES
CC(=O)c1ccc2ccccc2c1
LogP
2.678 at · 2.678 at 25℃
CAS データベース
93 · 93-08-3(CAS DataBase Reference)
NISTの化学物質情報
2 · 2-Naphthyl methyl ketone(93-08-3)
EPAの化学物質情報
2 · 2'-Acetonaphthone (93-08-3)
化学的性質 · 1 件

化学的特性2-Acetonaphthone smells similar to orange blossomand is a colorless crystalline solid (mp 56 °C). It is usually prepared by Friedel–Crafts acetylation of naphthalene (with acetyl chloride, acetic anhydride, etc.) in the presence of aluminumchloride. In polar solvents (e.g., nitrobenzene), the percentage of the simultaneously formed -isomer is lower. Methyl 2-naphthyl ketone is used in eau de cologne, soap perfumes, and detergents. It is a good fixative.

wgk
3
tsca
TSCA listed
rtecs
DB7084000
ridadr
UN3077
毒性
skn-hmn 100% FCTXAV 13,867,75
hs_code
29143900
risk_code
36/37/38-51/53-22-20/21/22
化審法
(4)-394
hazard_code
Xn,Xi,N
hazard_note
Irritant
safety_code
26-36-61-24/25-22-36/37
hazard_class
9
packing_group
III
Hazard Classifications
Aquatic Chronic 2
ストレージクラス
11 - Combustible Solids
· 6 件

0.2 [Products applied to the lips]

0.2 [Products applied to the axillae]

0.2 [Products applied to the face/body using fingertips]

0.2 [Products related to fine fragrances]

0.2 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.2 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

応用分野 · 2 件

使用2-Acetonaphthone is a flavoring agent that is a crystalline solid (white or nearly white) with orange blossom-like odor. It is soluble in most fixed oils, slightly soluble in mineral oil and propylene glycol, and insoluble in glycerin. It is obtained by chemical synthesis.

一般的な説明2-Acetonaphthone undergoes efficient photoreduction in the presence of tri-n-butylstannane as hydrogen donor. It is solubilized in air-saturated sodium dodecyl sulphate micelles in D2O or H2O by pulsed nitrogen laser photolysis for triplet sensitized production of singlet oxygen.

調製方法 · 2 件

製造方法2-Acetonaphthone may be prepared by Friedel-Crafts reaction of naphthalene, acetyl chloride and AlCl3.

純化方法Separate it from the 1-isomer by fractional crystallisation of the picrate in EtOH (see entry for the 1-isomer above) to m 82o. Decomposition of the picrate with dilute NaOH and extraction with Et2O, then evaporation, give purer 2-acetylnaphthalene. If this residue solidifies, it can be recrystallised from pet ether, EtOH or acetic acid; otherwise it should be distilled in a vacuum and the solid distillate is recrystallised [Gorman & Rodgers J Am Chem Soc 108 5074 1986, Levanon et al. J Phys Chem 91 14 1987]. Purity should be checked by high field NMR spectroscopy. Its oxime has m 145o(dec), and the semicarbazone has m 235o. [Stobbe & Lenzer Justus Liebigs Ann Chem 380 95 1911, Raffauf J Am Chem Soc 72 753 1950, Hunsberger J Am Chem Soc 72 5626 1950, Immediata & Day J Org Chem 5 512 1940, Beilstein 7 IV 1294.]

上流・下流製品情報

上流原料

塩化アルミニウム(III)2-イソプロペニルナフタレン2-ナフタレンボロン酸1-(2-ナフチル)エタノール2-ブロモアセチルナフタレン(2-ナフチル)アセチレンブチルビニルエーテル2-ブロモナフタレンスルファニル酸ジフェニルアミンBenzenesulfonic acid, 4-[[4-(nitrosophenylamino)phenyl]azo]-, nitro derivs.

下流製品

2-(2-Naphthyl)-1H-indole-3-carbaldehydeジフェニルジスルフィド(S)-(-)-1-(2-ナフチル)エタノール2-ナフトアルデヒド1'-アセトナフトン2‐(2‐ナフチル)アセチルクロリドN-(2-ナフチル)アセトアミド1-ブロモ-2-ナフチルアミン1-ブロモ-2-ヨードナフタレンZM 449829

補足説明

定義ChEBI: 2-acetylnaphthalene is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group.