67886-70-8

Usage

Uses

Used in Chemical Synthesis:
2-CYANO-6-METHOXYNAPHTHALENE is used as a key intermediate in the synthesis of 2-cyano-1-(1,3-diarylpropyl)-6-methoxynaphthalenes. These synthesized compounds have potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-CYANO-6-METHOXYNAPHTHALENE can be used as a building block for the development of new drugs with potential therapeutic properties. Its unique structure allows for the formation of various derivatives, which can be further modified to create novel drug candidates.
Used in Agrochemical Industry:
2-CYANO-6-METHOXYNAPHTHALENE can also be utilized in the agrochemical industry for the synthesis of new pesticides or herbicides. Its structural features can be exploited to design compounds with improved efficacy and selectivity, leading to more effective and environmentally friendly products.
Used in Materials Science:
In the field of materials science, 2-CYANO-6-METHOXYNAPHTHALENE can be employed in the development of advanced materials with specific properties, such as optical, electronic, or magnetic characteristics. Its incorporation into polymers or other materials can lead to the creation of novel materials with unique applications in various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4995, 1984 DOI: 10.1021/jo00199a048

InChI:InChI=1/C12H9NO/c1-14-12-5-4-10-6-9(8-13)2-3-11(10)7-12/h2-7H,1H3

Upstream product

• 5807-02-3 4-morpholinoacetonitrile 
• 55090-57-8 phenyl 6-methoxy-2-naphthoate 
• 82408-29-5 phenyl naphthalene-2-carboxylate 
• 874-77-1 2-(4-methylpiperazin-1-yl)acetonitrile 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 77287-34-4 formamide 
• 557-21-1 zinc(II) cyanide 
• 79215-28-4 6-methoxy-3,4-dihydronaphthalene-2-carbonitrile 
• 34093-07-7 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile 
• 606494-99-9 1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene 
• 16252-53-2 6-Methoxy-2-hydroxymethylen-1-tetralon 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 3453-33-6 6-methoxynaphthalene-2-carbaldehyde 
• 129113-00-4 2-ethynyl-6-methoxynaphthalene 

Downstream Products

• 3453-33-6 6-methoxynaphthalene-2-carbaldehyde 
• 52927-22-7 6-cyano-2-naphthol 
• 60201-22-1 (6-methoxy-2-naphthyl)methanol 
• 791-28-6 Triphenylphosphine oxide 
• 59115-50-3 2-methoxy-6-(4-methylphenyl)naphthalene 
• 93-04-9 2-Methoxynaphthalene 
• 1019477-32-7 N-((6-methoxynaphthalen-2-yl)methyl)propan-2-amine 
• 1402577-15-4 (6-methoxynaphthalen-2-yl)diphenylphosphine oxide 
• 1398119-47-5 C₂₇H₁₇NO₃ 
• 190434-38-9 6-benzyl-2-naphthalenol 
• 2471-69-4 6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid 
• 58601-32-4 6-methoxy-2-naphthoyl chloride 
• 199387-77-4 6-(aminomethyl)naphthalen-2-ol 
• 183231-93-8 [1-(6-Methoxy-naphthalen-2-yl)-ethyl]-phosphonic acid dibenzyl ester 

Relevant academic research and scientific papers

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.

Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy

Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.

Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)

The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)

A carboxamide is the cyanogen source of aromatic nitrile to the preparation method of the (by machine translation)

The invention discloses a method for preparing aromatic nitrile, is under the action of the nickel catalyst, in order to carboxamide is the cyanogen source, and with various substituents haloarene coupled reactions, preparing aromatic nitrile. The reaction temperature is 100 - 160 °C, the reaction time is 6 - 24 hours. It overcomes the traditional aromatic nitrile of the synthesis method operation of complex steps, requires the use of a toxic, more expensive, functionalization of the cyanogen source as the reaction raw material and the like. Compared with the traditional method, this method is simple to use cheap, green non-toxic of the formamide is cyano sources; without the need of external dehydrating agent, formamide in the nickel catalyst of the catalytic dehydration at the same time, with a nickel catalyst in coordination with the halogenated aromatic hydrocyanation, more economic, high-efficiency, environmental protection; at the same time the method exhibits good substrate universality, to air, moisture, light are not sensitive, high yield, product separation and purification is simple, with wide application. (by machine translation)

Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.

Synthesis method of benzonitrile compounds

The invention provides a preparation method of benzonitrile compounds. The preparation method comprises the steps: carrying out a reaction in an organic solvent at 0-50 DEG C for 4-12h under the action of an oxidant by taking phenylacetylene as shown in the formula (I) and a derivative of phenylacetylene as raw materials and nitrite as a nitrogen source, and separating and purifying the obtained reaction liquid to prepare the benzonitrile compound as shown in the formula (II); and the amount-of-substance ratio of the nitrogen source to phenylacetylene as shown in the formula (I) and the derivative of phenylacetylene is (1-3):1. The preparation method is simple and available in raw material, mild in reaction condition, good in functional group tolerance, simple in operation and environment-friendly so as to be a novel method for synthesizing benzonitrile containing various substituent groups.

Decarbonylative Cyanation of Amides by Palladium Catalysis

Transition-metal-catalyzed cyanation of aryl halides is a process of significant importance in the preparation pharmaceuticals, organic materials and agrochemicals. Here, we demonstrate a palladium-catalyzed decarbonylative cyanation of amides by highly selective carbon-nitrogen bond cleavage for the synthesis of a wide range of aryl nitriles. The utility of this technology is demonstrated by the synthesis of isotopically labeled aryl nitriles and orthogonal cross-coupling reactions of bench-stable amides to establish cross-coupling synthons with opposite polarity.

Design, Conformation, and Crystallography of 2-Naphthyl Phenyl Ethers as Potent Anti-HIV Agents

Catechol diethers that incorporate a 7-cyano-2-naphthyl substituent are reported as non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). Many of the compounds have 1-10 nM potencies toward wild-type HIV-1. An interesting conformational effect allows two unique conformers for the naphthyl group in complexes with HIV-RT. X-ray crystal structures for 4a and 4f illustrate the alternatives.

Aerobic Copper-Promoted Radical-Type Cleavage of Coordinated Cyanide Anion: Nitrogen Transfer to Aldehydes to Form Nitriles

We have disclosed for the first time the copper-promoted C≡N triple bond cleavage of coordinated cyanide anion under a dioxygen atmosphere, which enables a nitrogen transfer to various aldehydes. Mechanistic study of this unprecedented transformation suggests that the single electron-transfer process could be involved in the overall course. This protocol provides a new cleavage pattern for the cyanide ion and would eventually lead to a more useful synthetic pathway to nitriles from aldehydes.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).