93-08-3 Usage
Description
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.
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.
93-08-3Relevant articles and documents
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Pampel,Schmidt
, p. 2898 (1886)
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Lock
, p. 77,81 (1943)
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Bassilios et al.
, p. 72 (1954)
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.
Mechanistic Studies on the Hexadecafluorophthalocyanine–Iron-Catalyzed Wacker-Type Oxidation of Olefins to Ketones**
Grinenko, Vadim,Klau?, Hans-Henning,Kn?lker, Hans-Joachim,Puls, Florian,Seewald, Felix
, p. 16776 - 16787 (2021/11/04)
The hexadecafluorophthalocyanine–iron complex FePcF16 was recently shown to convert olefins into ketones in the presence of stoichiometric amounts of triethylsilane in ethanol at room temperature under an oxygen atmosphere. Herein, we describe an extensive mechanistic investigation for the conversion of 2-vinylnaphthalene into 2-acetylnaphthalene as model reaction. A variety of studies including deuterium- and 18O2-labeling experiments, ESI-MS, and 57Fe M?ssbauer spectroscopy were performed to identify the intermediates involved in the catalytic cycle of the oxidation process. Finally, a detailed and well-supported reaction mechanism for the FePcF16-catalyzed Wacker-type oxidation is proposed.
