33744-50-2

Usage

Uses

1. Used in Pharmaceutical Industry:
1-(naphthalen-1-yl)propan-2-one is used as a synthetic intermediate for the production of 6-Methyl Chrysene (M265140), an aryl hydrocarbon receptor (AhR) agonist. 1-(naphthalen-1-yl)propan-2-one has been listed as possibly carcinogenic to humans, and its synthesis is of interest for research and development purposes in the pharmaceutical industry.
2. Used in Chemical Synthesis:
1-(naphthalen-1-yl)propan-2-one serves as a valuable building block in the synthesis of various organic compounds, including those with potential applications in different industries such as agriculture, materials science, and environmental science. Its unique structure allows for further functionalization and modification to create new molecules with specific properties and applications.

Synthesis Reference(s)

Tetrahedron, 50, p. 11839, 1994 DOI: 10.1016/S0040-4020(01)89299-1Tetrahedron Letters, 26, p. 3777, 1985 DOI: 10.1016/S0040-4039(00)89248-5

InChI:InChI=1/C13H12O/c1-10(14)9-12-7-4-6-11-5-2-3-8-13(11)12/h2-8H,9H2,1H3

Upstream product

• 13098-88-9 naphthalen-1-ylmethyl acetate 
• 91-20-3 naphthalene 
• 67-64-1 acetone 
• 90-13-1 1-Chloronaphthalene 

Downstream Products

• 101759-44-8 2-Naphthalen-1-yl-4-nitro-phenol 
• 24258-13-7 1-(1'-naphthyl)-2-benzylaminopropane 
• 102421-51-2 1-(1-naphthyl)-2-propanone p-nitrobenzoyloxime 
• 86-53-3 1-Cyanonaphthalene 
• 1491163-05-3 (E,E)-2,5-bis{2-[4-(dipropylamino)phenyl]ethenyl}-3,6-di(1-naphthyl)pyrazine 
• 1491163-04-2 (E,E)-2,5-bis[2-(4-hexyloxyphenyl)ethenyl]-3,6-di(1-naphthyl)pyrazine 
• 89845-24-9 2-bromo-1-(naphth-1-yl)-1-propanone 
• 33744-54-6 4-Acetyl-4-α-naphthylcyclohexanon 
• 33732-67-1 1-Benzoyl-4-(α-naphthyl)bicyclo<2.2.2>octane 
• 75250-89-4 (E)-N-<1-Methyl-2-(1-naphthyl)ethyliden>benzolamin 
• 75250-88-3 (Z)-N-<1-Methyl-2-(1-naphthyl)ethyliden>benzolamin 
• 101712-57-6 N-(3-Diethylaminomethyl-4-hydroxy-5-naphthalen-1-yl-phenyl)-acetamide 
• 101712-38-3 N-(4-Hydroxy-3-naphthalen-1-yl-phenyl)-acetamide 

Relevant academic research and scientific papers

Reaction of Benzyl and Naphthylmethyl Esters with Arene Radical Anions

The reactions of four esters, naphth-1-ylmethyl acetate, naphth-1-ylmethyl benzoate, benzyl acetate, and benzyl benzoate, with the salts of radical anions of fluoranthene and biphenyl have been studied.When ester radical anion formation is energetically possible, CH2-O bond cleavage follows rapidly.The resultant ArCH2 radical is reduced under the reaction conditions.The ArCH2 anion thus produced can react with the ester both as a nucleophile and as a base to promote a variety of side reactions.In most cases, these processes compete with the initial reduction and cleavage.

SRN1 reactions of aryl halides with carbanions initiated by sodium amalgam in liquid ammonia

The reaction of 1-chloronaphthalene with acetone (2a) and acetophenone (2b) enolate ions was initiated by sodium amalgam [Na(Hg)] in liquid ammonia giving good yields of the substitution products 3a and 3b respectively. 2-Chloroquinoline and 2-chloropyridine gave good yields of substitution product with 2b, and moderate to good yields with 2a. 4-Bromobenzophenone and 2a gave 78% of the substitution product 5. With aryl halides whose radical anions fragment fast and consequently close to the Na(Hg) surface, such as bromobenzene and p-bromoanisole, only dehalogenation products were observed. However, when benzonitrile was used as a redox catalyst, about 50% of the substitution product 6 was obtained with p-bromoanisole and 2a. However, with the more reactive carbanionic nucleophile, such as anthrone anion 4, good yields of the substitution product 7 were obtained with bromobenzene. In all these reactions neither reduction of the aromatic moiety nor the ketone functionality was observed. It is therefore suggested that Na(Hg) amalgam initiates these SRN1 reactions.

Aromatic Acetonylation Promoted by Manganese(III) and Cerium(IV) Salts

Treatment of aromatic hydrocarbons with acetone and manganese(III) acetate gave rise to arylacetones in yields ranging from 25 percent with chlorobenzene to 74 percent with anisole.Cerium(IV) salts were also successfully used as promoters but gave lower yields.The reactions were relatively free of side products except with toluene.Isomer distributions, relative rates, and partial rate factors were determined for acetonylation of anisole, toluene, chlorobenzene, and fluorobenzene.A Hammett plot of the log of the partial rate factors for the manganese(III) system vs. ?-constants gave a slope, ρ, of -2.4 +/- 0.3.An isotope effect kH/kD = 3.8 was observed for the manganese(III)-promoted reaction with acetone-d6, indicating rate-determining proton loss from acetone.The overall mechanism involves formation and attack of acetonyl radicals onto the aromatic hydrocarbon followed by subsequent oxidative deprotonation of the resulting ?-radical complex.The acetonyl radical exhibits appreciable electron-deficient character in its substitution behavior with aromatic hydrocarbons.