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.]

Upstream product

• 463-51-4 Ketene 
• 91-20-3 naphthalene 
• 917-64-6 methyl magnesium iodide 
• 613-46-7 2-naphthalenecarbonitrile 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 941-98-0 1'-naphthacetophenone 
• 506-96-7 Acetyl bromide 
• 111-34-2 -butyl vinyl ether 
• 580-13-2 2-bromonaphthalene 
• 3622-76-2 (2-ethenyloxyethyl)dimethylamine 
• 3857-83-8 2-naphthyl triflate 
• 750634-70-9 2-naphthyl triflate 
• 1146-65-2 naphthalene-d8 

Downstream Products

• 5399-06-4 2-naphthylthioacetic acid morpholylamide 
• 15462-59-6 2-(3--acryloyl)-naphthalin 
• 104765-79-9 (2E)-1-(2-naphthyl)-3-(4-fluorophenyl)-2-propen-1-one 
• 22359-67-7 3-(4-methoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one 
• 1201-74-7 1-(2-Naphthyl)ethylamine 
• 13298-50-5 1-methyl-3-(2-naphthyl)propane-1,3-dione 
• 81826-91-7 methyl β-(naphthyl)crotonate 
• 21331-43-1 2-amino-4-(2-naphthyl)thiazole 
• 93-09-4 naphthalene-2-carboxylate 
• 36983-38-7 ethyl 4-(naphthalen-2-yl)-2,4-dioxobutanoate 
• 10432-43-6 2-(1-(naphthalen-6-yl)ethylidene)malononitrile 
• 15473-67-3 1-(naphthalen-3-yl)-3-phenyl-3-thioxopropan-1-one 
• 69470-14-0 1-(2-Naphthyl)-1.1-bis(phenylseleno)aethan 
• 73265-81-3 2-(4-naphthalen-2-yl-thiazol-2-ylamino)-benzenethiol 

Relevant academic research and scientific papers

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

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

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

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

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

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

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%.

Iron-Catalyzed Wacker-type Oxidation of Olefins at Room Temperature with 1,3-Diketones or Neocuproine as Ligands**

Herein, we describe a convenient and general method for the oxidation of olefins to ketones using either tris(dibenzoylmethanato)iron(III) [Fe(dbm)3] or a combination of iron(II) chloride and neocuproine (2,9-dimethyl-1,10-phenanthroline) as catalysts and phenylsilane (PhSiH3) as additive. All reactions proceed efficiently at room temperature using air as sole oxidant. This transformation has been applied to a variety of substrates, is operationally simple, proceeds under mild reaction conditions, and shows a high functional-group tolerance. The ketones are formed smoothly in up to 97 % yield and with 100 % regioselectivity, while the corresponding alcohols were observed as by-products. Labeling experiments showed that an incorporated hydrogen atom originates from the phenylsilane. The oxygen atom of the ketone as well as of the alcohol derives from the ambient atmosphere.

Chiral Yolk-Shell MOF as an Efficient Nanoreactor for Asymmetric Catalysis in Organic-Aqueous Two-Phase System

It remains a great challenge to introduce large and efficient homogeneous asymmetric catalysts into MOFs and other microporous materials as well as retain their degrees of freedom. Herein, a new heterogeneous strategy of homogeneous chiral catalysts is proposed, that is, to construct a yolk-shell MOFs-confined, large-size, and highly efficient homogeneous chiral catalyst, which can be used as a nanoreactor for asymmetric catalytic reactions.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.