17579-79-2

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYL-2-NAPHTHOL is used as a reactant for the preparation of dioncoquinone derivatives, which possess anti-tumoral activities. These derivatives have the potential to be developed into pharmaceutical compounds for the treatment of various types of cancer.
Used in Chemical Synthesis:
6-METHYL-2-NAPHTHOL can also be utilized as a building block or intermediate in the synthesis of various organic compounds, including dyes, pigments, and other specialty chemicals. Its unique chemical structure allows for further functionalization and modification to create a wide range of products with different applications.

Purification Methods

Crystallise the naphthol from EtOH or ligroin. Sublime it in vacuo.[Beilstein 6 II 618, 6 III 3028.]

InChI:InChI=1/C11H10O/c1-8-2-3-10-7-11(12)5-4-9(10)6-8/h2-7,12H,1H3

Upstream product

• 13035-04-6 sodium 6-methyl-2-naphthalene sulfonate 
• 52986-50-2 6-methyl-2-naphthyl acetate 
• 26386-94-7 2-methyl-6-methoxynaphthalene 
• 288-32-4 1H-imidazole 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 5111-66-0 6-Methoxy-2-naphthol 
• 75-16-1 methylmagnesium bromide 
• 1251910-25-4 1-(6-hydroxynaphthalen-2-yl)-N,N,N-trimethylmethanaminium iodide 
• 60-24-2 2-hydroxyethanethiol 
• 1251910-26-5 6-((2-hydroxyethylthio)methyl)naphthalen-2-ol 
• 1251910-23-2 6-[(dimethylamino)methyl]naphthalen-2-ol 
• 52927-22-7 6-cyano-2-naphthol 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 37796-79-5 6-methylnaphthalen-2-amine 
• 172170-94-4 1,1'-bi-(6-methyl-2-naphthol) 
• 26386-94-7 2-methyl-6-methoxynaphthalene 
• 398-38-9 (4-fluoro-phenyl)-(6-methyl-[2]naphthyl)-amine 
• 612-94-2 2-phenylnaphthalene 
• 29304-66-3 2-methyl-6-phenylnaphthalene 
• 663189-38-6 2-Methyl-3-hydroxy-6-methoxy-1,4-naphthochinon 
• 132041-61-3 2-methyl-6-p-tolylnaphthalene 

Relevant academic research and scientific papers

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX

Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.

Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols

Presented here is a class of novel axially chiral aryl-p-quinones as platform molecules for the preparation of non-C2 symmetric biaryldiols. Two sets of aryl-p-quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p-quinones by central-to-axial chirality conversion. These aryl-p-quinones were then used to access a wide spectrum of highly functionalized non-C2 symmetric biaryldiols with excellent retention of the enantiopurity.

Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

Ligand-controlled regiodivergent π-allyl palladium catalysis enables a switch between [3+2] and [3+3] cycloadditions

Reported herein is the use of ligands to tune the regioselectivity and reactivity of palladium-catalyzed [3+2] and [3+3] cycloadditions. Diverse synthesis with vinylethylene carbonates (VECs) as well as free naphthols has been explored to construct four different valuable polycyclic frameworks in a broad substrate scope.

Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: Synthesis of dihydrofuran derivatives

A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.

Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes

Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.

Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols

The iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the intermolecular allylation of naphthol derivatives to give the corresponding partially dearomatized allylated chromenones in good to excellent yields. The scope and limitations are reported. An efficient decarboxylative intramolecular C-allylation, starting from allyl naphthyl carbonates, was developed. From a mechanistic point of view, the overall process is the result of a fast O-allylation followed by a sigmatropic rearrangement to the desired product.

Simple and efficient one-step conversion of benzonitrile into methylarene under mild conditions

A very simple and efficient method has been developed for the synthesis of various methylarenes from the corresponding benzonitriles under mild conditions. The protocol uses Pearlmans catalyst to achieve the transformation under an atmosphere of gaseous hydrogen and proceeds smoothly in many common solvents. A series of methylarenes were thus obtained in high yields and purities. Georg Thieme Verlag Stuttgart - New York.

Protecting group free synthesis of 6-substituted naphthols and binols

A straightforward route for the preparation of 6-substituted naphthols and 6,6′-disubstituted binols (binol = 2,2′-dihydroxy-1,1′- binaphthyl) is presented. The synthesis has been accomplished by a one-step procedure starting from 6-bromo derivatives via direct lithiation with n-BuLi, followed by the addition of several electrophiles. This C-C functionalization has been successfully achieved with iodomethane, 3-methoxybenzaldehyde, benzophenone, methyl-2-methylbenzoate, methylbenzoate, dimethyl carbonate, ethyl 2-chloro-2-oxoacetate, and 2,2-dimethyloxirane (E). This reactivity offers a useful protecting group free synthetic protocol, toward chiral disubstituted 6,6′-binols with configuration retention of the binol moiety.