613-46-7

Usage

Chemical Properties

off-white to beige crystalline powder

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 6729, 1990 DOI: 10.1021/ja00174a053Synthesis, p. 223, 1989 DOI: 10.1055/s-1989-27210

InChI:InChI=1/C11H7N/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H

Upstream product

• 1166-32-1 N,N'-di(2-naphthyl)thiourea 
• 3007-91-8 ethyl-2-naphthoate 
• 120-18-3 naphthalene-2-sulfonate 
• 151-50-8 potassium cyanide 
• 4423-74-9 2-formamidonaphthalene 
• 7657-86-5 tri(naphthalen-2-yl) phosphate 
• 143-33-9 sodium cyanide 
• 532-02-5 2-naphthalenesulfonic acid sodium salt 
• 91-59-8 naphthalen-2-ylamine 
• 2243-82-5 2-naphthamide 
• 1131-33-5 2-phenylpyridin N-oxide 
• 603-71-4 nitromesitylene 
• 3857-83-8 2-naphthyl triflate 
• 51873-98-4 2-naphthaldoxime 

Downstream Products

• 7496-04-0 naphthalen-2-yl(o-tolyl)methanone 
• 93-08-3 methyl 2-naphthyl ketone 
• 859946-73-9 di(naphthalen-2-yl)methanimine 
• 6315-96-4 1-(2-naphthyl)-1-propanone 
• 113698-36-5 Benazoline 
• 644-13-3 C₆H₅COC₁₀H₇ 
• 2243-82-5 2-naphthamide 
• 1592-38-7 2-Naphthalenemethanol 
• 23245-67-2 5-nitro-2-naphthonitrile 
• 612-17-9 1,4-dihydronaphthalene 
• 2018-90-8 naphthalen-2-ylmethylamine 
• 47304-99-4 bis((naphthalen-2-yl)methyl)amine 
• 6967-89-1 naphthalene-2-carbothioamide 
• 73399-86-7 5-chloro-[2]naphthonitrile 

Relevant academic research and scientific papers

Photocycloaddition of Cyanonaphthalenes to 1,3-Cyclohexadiene

To prevent secondary processes due to facile thermal reaction, low-temperature irradiations of cyanonaphthalenes and 1,3-cyclohexadiene through a Pyrex filter were conducted. Along with the identification of the products, the results of the triplet-sensitized photoreaction of the irradiated mixture, low-temperature 1H NMR study of the irradiated mixture, and the Cope rearrangement reaction of some products suggested that the primary major products are the corresponding exo-[4 + 4] adducts fused at 1,4 position of the naphthalene skeleton and the syn-[2 + 2] adducts fused at 1,2 position. The formations of the primary products in these singlet-state photocycloaddition reactions were interpreted by primary and secondary orbital interactions. A rationalization for the previous results on the photoreactions at room temperature was also provided.

β-naphthalene incorporated thiazole-5-carboxamides/thiazole -5- ketones: Design, synthesis and anticonvulsant screening against two seizure models

A bunch of β-naphthalene incorporated thiazole-5-carboxamides/thiazole -5- ketones (7a-7o& 8a-8e) were prepared by reacting 4-methyl-2-(naphthalen-2-yl)thiazole-5-carbonyl chloride with appropriate amines. Structures of all the compounds were explained by elemental analysis, FT-IR, 1H NMR and mass spectral data. The compounds were evaluated for their anticonvulsant activity employing MES and chemoshock (scPTZ) seizure tests. Neurotoxicity was also assessed. Majority of these compounds exhibited significant activity against both animal models; however, compounds 7e, 7j, 7n and 8c displayed promising activity and could be considered as leads for further investigations.

Photoinduced Electron Transfer Reaction of Mono- and Dicyanonaphthalenes with Allyltrimethylsilane: Synthesis of Benzotricyclo3,8>nonenes by Reductive Photoallylation and Intramolecular (2? + 2?) Photocycloaddition

Irradiation of an acetonitrile-methanol (4:1) solution containing 1-cyanonaphthalene and allyltrimethylsilane (1) through Pyrex filter (>280 nm) regioselectively gave 3-cyano-4,5-benzotricyclo3,8>-4-nonene.The photoreaction of 2-cyanonaphthalene, 1-cyano-2-methylnaphthalene, 1-cyano-4-methylnaphthalene, 1,5- and 2,3-dicyanonaphthalenes with 1 gave the corresponding benzotricyclic compounds also in a regioselective manner.However, the photorection of 2,3-disubstituted 1,4-dicyanonaphthalenes with 1 gave no benzotricyclic compounds, but only the allyl substitution and reductive allylation products.These photoreactions were initiated by photoinduced electron transfer from 1 to the excited singlet states of mono- and dicyanonaphthalenes.The reductive allylation products from the former cyanonaphthalenes afforded the benzotricyclic compounds by an intramolecular (2? + 2?) photocycloaddition in good yields.The regioselectivity in the allylation reaction is discussed on the basis of the results of MO calculations of the radical anions of mono- and dicyanonaphthalenes.

Concentration-dependent isotope effects. The photocyanation of naphthalene

Concentration-dependent isotope effects (IEs) were measured in the competitive photocyanation of naphthalene and perdeuterionaphthalene in acetonitrile in the presence of electron acceptors. The concentration of the reagents naphthalene, cyanide, and oxygen influences the magnitude of the IE. Experiments in which the photocyanation is brought about via selective excitation of an electron acceptor show that the naphthalene-concentration dependence of the IEs is not caused by the naphthalene radical cations, which are intermediates in the photoreaction. This is corroborated by an electrochemical study of (the reactivity of) these radical cations. From these observations and complementary semiempirical PM3 calculations it is concluded that the variation of the IE with naphthalene concentration is due to an excited-state equilibration. A detailed reaction mechanism is proposed to account for the observed IEs.

Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones

The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.

Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst

A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.

Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles

Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.