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2-Acetonaphthone, also known as Methyl β-napthyl ketone, is a colorless crystalline solid with a floral, neroli odor suggestive of orange blossom and a strawberry-like flavor. It is a naphthyl ketone that is naphthalene substituted at position 2 by an acetyl group. It is usually prepared by Friedel-Crafts acetylation of naphthalene in the presence of aluminum chloride. It is soluble in most fixed oils, slightly soluble in mineral oil and propylene glycol, and insoluble in glycerin.

93-08-3

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93-08-3 Usage

Uses

Used in Flavoring Industry:
2-Acetonaphthone is used as a flavoring agent for its orange blossom-like odor and strawberry-like flavor. It is used in the production of various food and beverage products.
Used in Perfumery Industry:
2-Acetonaphthone is used as a fixative in eau de cologne, soap perfumes, and detergents due to its floral, neroli odor.
Used in Chemical Research:
2-Acetonaphthone is used in direct time-resolved studies on singlet molecular oxygen phosphorescence in heterogeneous silica gel/cyclohexane systems.
Used in Photochemistry:
2-Acetonaphthone undergoes efficient photoreduction in the presence of tri-n-butylstannane as a hydrogen donor. It is solubilized in air-saturated sodium dodecyl sulfate micelles in D2O or H2O by pulsed nitrogen laser photolysis for triplet sensitized production of singlet oxygen.

Preparation

Prepared by Friedel–Crafts reaction of naphthalene, acetyl chloride and AlCl3.

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 3101, 1977 DOI: 10.1021/ja00451a041The Journal of Organic Chemistry, 55, p. 319, 1990 DOI: 10.1021/jo00288a054Tetrahedron Letters, 19, p. 147, 1978 DOI: 10.1016/S0040-4039(01)85068-1

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Odor at 1.0%

Safety Profile

Moderately toxic by ingestion. A human skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and fumes

Purification Methods

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 93-08-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 93-08:
(4*9)+(3*3)+(2*0)+(1*8)=53
53 % 10 = 3
So 93-08-3 is a valid CAS Registry Number.

93-08-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A14793)  2-Acetylnaphthalene, 99%   

  • 93-08-3

  • 50g

  • 214.0CNY

  • Detail
  • Alfa Aesar

  • (A14793)  2-Acetylnaphthalene, 99%   

  • 93-08-3

  • 100g

  • 251.0CNY

  • Detail
  • Alfa Aesar

  • (A14793)  2-Acetylnaphthalene, 99%   

  • 93-08-3

  • 250g

  • 500.0CNY

  • Detail
  • Alfa Aesar

  • (A14793)  2-Acetylnaphthalene, 99%   

  • 93-08-3

  • 1000g

  • 1886.0CNY

  • Detail
  • Sigma-Aldrich

  • (18478)  2-Acetonaphthone  analytical standard

  • 93-08-3

  • 18478-100MG

  • 458.64CNY

  • Detail

93-08-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-acetylnaphthalene

1.2 Other means of identification

Product number -
Other names 2'-Acetonaphthone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:93-08-3 SDS

93-08-3Relevant articles and documents

Fluorescence and phosphorescence of α- and β-isomers of boron Difluoride naphthaloylacetonates

Fedorenko, Elena V.,Mirochnik, Anatolii G.,Gerasimenko, Andrey V.,Beloliptsev, Anton Yu.,Puzyrkov, Zakhar N.,Svistunova, Irina V.,Sergeev, Aleksander A.

, (2021)

A comparative study of the luminescence properties of solutions and crystals of two isomers: boron difluoride 1-(1′-naphthyl)butanedionate-1,3 (α-NAcBF2) and 1-(2′-naphthyl)butanedionate-1,3 (β-NAcBF2) has been performed. An interrelation between the molecular and crystal structure of the studied complexes and their luminescence properties has been revealed. In the α-NAcBF2 molecule, the plane of the naphthyl group was turned by 34.26° relatively to the chelate cycle, while the β-NAcBF2 molecule was planar. The difference in the luminescence properties of the crystals of α-NAcBF2 (452 nm) and β-NAcBF2 (537 nm) was related to different abilities to form excimers. In β-NAcBF2 crystals, J-aggregates consisted of dimers of antiparallel molecules comprising excimer traps. For the crystals and solutions of α-NAcBF2 at 77 K, in addition to phosphorescence, the delayed fluorescence was observed. In case of β-NAcBF2, the delayed fluorescence was detected only for crystals, whereas the phosphorescence – for both crystals and solutions.

1-butyl-3-methylimidazolium cobalt tetracarbonyl [bmim][Co(CO)4]: A catalytically active organometallic ionic liquid

Brown,Dyson,Ellis,Welton

, p. 1862 - 1863 (2001)

An ambient temperature liquid transition metal carbonyl anion has been prepared in a metathesis reaction between [bmim]Cl ([bmim]+ = 1-butyl-3-methylimidazolium cation) and Na[Co(CO)4]; the ionic liquid catalyses the debromination of 2-bromoketones.

Enantioselective electrocatalytic oxidation of racemic sec-alcohols using a chiral 1-azaspiro[5.5]undecane-N-oxyl radical

Kashiwagi, Yoshitomo,Kurashima, Futoshi,Kikuchi, Chikara,Anzai, Jun-ichi,Osa, Tetsuo,Bobbitt, James M.

, p. 6469 - 6472 (1999)

Nitroxyl radical (6S,7R,10R)-4-acetylamino-2,2,7-trimethyl-10-isopropyl- 1-azaspiro[5.5]-undecane-N-oxyl reveals a reversible redox peak in cyclic voltammetry at + 0.62 V vs. Ag/AgCl. A preparative electrocatalytic oxidation of racemic sec-alcohols on the nitroxyl radical yielded mixtures of 51.4 - 63.9 % ketones and 36.1 - 48.6 % alcohols by 10 h of electrolysis. The current efficiency and turnover number of the reactions were 85.6 - 87.9 % and 20.6 - 25.6, respectively. The enantiopurity of the remaining (R)-isomers was 50 - 70 % and the S values as a selective factor was 4.1 - 4.6.

Synthesis of Visible-Light–Activated Hypervalent Iodine and Photo-oxidation under Visible Light Irradiation via a Direct S0→Tn Transition

Matsuda, Yu,Matsumoto, Koki,Nagasawa, Sho,Nakajima, Masaya,Nemoto, Tetsuhiro

, p. 235 - 239 (2022/03/16)

Heavy atom-containing molecules cause a photoreaction by a direct S0→Tn transition. Therefore, even in a hypervalent iodine compound with a benzene ring as the main skeleton, the photoreaction proceeds under 365–400nm wavelength light, where UV-visible spectra are not observed by usual measurement method. Some studies, however, report hypervalent iodine compounds that strongly absorb visible light. Herein, we report the synthesis of two visible light-absorbing hypervalent iodines and their photooxidation properties under visible light irradiation. We also demonstrated that the S0→Tn transition causes the photoreaction to proceed under wavelengths in the blue and green light region.

Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free

Burns, David J.,Lee, Ai-Lan,McLean, Euan B.,Mooney, David T.

supporting information, p. 686 - 691 (2022/01/28)

A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge

supporting information, p. 1372 - 1377 (2022/02/23)

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis

Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan

supporting information, p. 6781 - 6785 (2021/08/20)

A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.

Selective oxidation of alkenes to carbonyls under mild conditions

Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan

supporting information, p. 5549 - 5555 (2021/08/16)

Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

Du, Dongdong,Luo, Junfei,Shi, Sanshan,Xie, Pan,Xue, Cheng

, p. 5936 - 5943 (2021/08/23)

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

Visible-Light-Driven Oxidative Cleavage of Alkenes Using Water-Soluble CdSe Quantum Dots

Li, Jianing,Zhao, Jingnan,Ma, Cunfei,Yu, Zongyi,Zhu, Hongfei,Yun, Lei,Meng, Qingwei

, p. 4985 - 4992 (2021/10/16)

The oxidative cleavage of C=C bonds is an important chemical reaction, which is a popular reaction in the photocatalytic field. However, high catalyst-loading and low turnover number (TON) are general shortcomings in reported visible-light-driven reactions. Herein, the direct oxidative cleavage of C=C bonds through water-soluble CdSe quantum dots (QDs) is described under visible-light irradiation at room temperature with high TON (up to 3.7×104). Under the same conditions, water-soluble CdSe QDs could also oxidize sulfides to sulfoxides with 51–84 % yields and TONs up to 3.4×104. The key features of this photocatalytic protocol include high TONs, wide substrates scope, low catalyst loadings, simple and mild reaction conditions, and molecular O2 as the oxidant.

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