71056-96-7

Usage

Uses

Used in Organic Synthesis:
2-(6-Methoxy-2-naphthyl)acetonitrile is used as a key intermediate for the synthesis of various organic compounds. Its chemical structure allows it to be a versatile building block in the development of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(6-Methoxy-2-naphthyl)acetonitrile is used as a starting material for the development of new drugs. Its unique chemical properties enable the creation of novel drug candidates that can potentially target specific diseases or conditions.
Used in Chemical Research:
2-(6-Methoxy-2-naphthyl)acetonitrile is also used in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methods. Its reactivity and structural features make it an ideal candidate for exploring new chemical pathways and understanding the underlying principles of organic chemistry.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 2-(6-Methoxy-2-naphthyl)acetonitrile can be used as a precursor for the synthesis of various dyes and pigments. Its yellow color and chemical properties make it a suitable candidate for the development of new colorants with improved properties, such as enhanced stability and color intensity.
Used in Material Science:
2-(6-Methoxy-2-naphthyl)acetonitrile can also be employed in the field of material science for the development of new materials with specific properties. Its chemical structure can be used to create novel polymers, coatings, or other materials with unique characteristics, such as improved mechanical strength, thermal stability, or chemical resistance.

InChI:InChI=1/C13H11NO/c1-15-13-5-4-11-8-10(6-7-14)2-3-12(11)9-13/h2-5,8-9H,6H2,1H3

Upstream product

• 73022-40-9 2-(Bromomethyl)-6-methoxynaphthalene 
• 143-33-9 sodium cyanide 
• 41790-33-4 2-(chloromethyl)-6-methoxynaphthalene 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 557-21-1 zinc(II) cyanide 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 3453-33-6 6-methoxynaphthalene-2-carbaldehyde 
• 60201-22-1 (6-methoxy-2-naphthyl)methanol 
• 2471-70-7 2-methoxy-6-naphthoic acid 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 773837-37-9 sodium cyanide 

Downstream Products

• 23981-48-8 methyl 6-methoxy-2-naphthylacetate 
• 22204-53-1 (2S)-2-(6-methoxy(2-naphthyl))propanoic acid 
• 23981-47-7 6-methoxy-2-naphthylacetic acid 
• 196087-87-3 N-[2-(6-Methoxynaphthyl)ethyl]-4-methoxybenzamide 

Relevant academic research and scientific papers

Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.

Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation

A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl2dppf, KF, DMSO/H2O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.

Mild palladium-catalyzed selective monoarylation of nitriles

Two new palladium-catalyzed procedures for the arylation of nitriles under less basic conditions than previously reported have been developed. The selective monoarylation of acetonitrile and primary nitriles has been achieved using α-silyl nitriles in the presence of ZnF2. This procedure is compatible with a variety of functional groups, including cyano, keto, nitro, and ester groups, on the aryl bromide. The arylation of secondary nitriles occurred in high yield by conducting reactions with zinc cyanoalkyl reagents. These reaction conditions tolerated base-sensitive functional groups, such as ketones and esters. The combination of these two methods, one with a-silyl nitriles and one with zinc cyanoalkyl reagents, provides a catalytic route to a variety of benzylic nitriles, which have not only biological significance but utility as synthetic intermediates. The utility of these new coupling reactions has been demonstrated by a synthesis of verapamil, a clinically used drug for the treatment of heart disease, by a three-step route from commercial materials that allows convenient variation of the aryl group.

NAPTHTHALENE DERIVATIVES WHICH INHIBIT THE CYTOKINE OR BIOLOGICAL ACTIVITY OF MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF)

Where Y, R1-R8 and R101-R108 are as defined in the specification. Compounds of formula (II) and methods of inhibiting the cytokine or biological activity of Macrophage Migrating Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as part of a combination therapy.

Antihyperglycemic Activity of Novel Naphthalenyl 3H-1,2,3,5-Oxathiadiazole 2-Oxides

A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus.Substitution at the 1-,5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4--3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.