2-Acetylnaphthalene (HCID 7122)

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

XLogP: 3.2
極性表面積: 17.1 Å²
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

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.

安全と法規制

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

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

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; Î²-Acetylnaphthalene; Cetone d; Ethanone, 1-(2-naphthalenyl); Î²-Methyl naphthyl ketone; Î²-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-AcetylnaphthaleneÃ¢â¬Â¨ in the following categories is provided:

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.]

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補足説明

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

2'-アセトナフトン

基本情報

概要