3378-82-3

Usage

Uses

Used in Chemical Synthesis:
1-Bromo-2-naphthaldehyde is used as a reagent for the synthesis of Hoveyda-Grubbs type metathesis catalysts, which are essential in cross olefin metathesis. These catalysts play a significant role in the formation of new carbon-carbon double bonds, which are vital in the development of various chemical compounds and materials.
Used in Pharmaceutical Industry:
1-Bromo-2-naphthaldehyde is also utilized in the preparation of novel (-)-cercosporamide derivatives, which act as potent and selective PPARγ modulators. PPARγ modulators have potential applications in the treatment of type 2 diabetes, inflammatory diseases, and certain types of cancer. The development of these derivatives contributes to the advancement of therapeutic options in the pharmaceutical industry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4617, 1981 DOI: 10.1021/jo00335a076

InChI:InChI=1/C11H7BrO/c12-11-9(7-13)6-5-8-3-1-2-4-10(8)11/h1-7H

Upstream product

• 37763-43-2 1-bromo-2-(bromomethyl)naphthalene 
• 64689-70-9 1-bromo-2-(methoxymethyl)naphthalene 
• 35810-04-9 benzenesulfinic acid cyclohexylamide 
• 76635-70-6 (1-bromo-2-naphthyl)methanol 
• 127349-02-4 1-bromo-2-(dibromomethyl)naphthalene 
• 91-57-6 2-Methylnaphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 

Downstream Products

• 116402-71-2 3-(1-bromo-[2]naphthyl)-2-phenyl-acrylic acid 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 101737-31-9 1-bromo-2-(2-methyl-benzyl)-naphthalene 
• 108978-33-2 2-benzyl-1-bromonaphthalene 
• 80409-67-2 1-(1-naphthyl)-naphthalene-2-carbaldehyde 
• 883221-33-8 1-(o-tolyl)naphthalene-2-carbaldehyde 
• 883221-32-7 1-(3,4,5-trimethoxyphenyl)-naphthalene-2-carbaldehyde 
• 169233-83-4 1-bromo-2-ethenylnaphthalene 
• 279245-83-9 2-[2-[(4'-chloro-[1,1'-biphenyl]-4-yl)oxy]ethyl]-1-bromonaphthalene 
• 279245-84-0 2-[2-[(4'-chloro-[1,1'-biphenyl]-4-yl)oxy]ethyl]-1-naphthoic acid 
• 68427-26-9 4-(naphthalen-2-yl)butan-2-one 
• 59632-40-5 2-(1-Bromo-2-naphthylmethylamino)-1-phenyl-1-propanol hydrochloride 
• 71382-61-1 1-phenylnaphthalene-2,2'-dicarboxaldehyde 
• 1084904-40-4 1-(2-isopropoxyphenyl)-2-naphthaldehyde 

Relevant academic research and scientific papers

A New Strategy for the Synthesis of Axially Chiral Biaryl Compounds

Axially chiral compounds can be synthesized in high atropisomeric purity by aryl coupling of a conformationally locked dihydroxy-stilbenoids, which are readily available via Sharpless asymmetric dihydroxylation of olefin precursors.

Synthesis of Naphthocyclobutenes from α-Naphthyl Acrylates by Visible-Light Energy-Transfer Catalysis

Methyl (α-naphthyl) acrylates bearing an ortho-substituent with a hydrogen atom produce naphthocyclobutenes upon Ir(Fppy)3-mediated photosensitization. This reaction can be described as a carbon analogue of the Norrish-Yang reaction: upon triplet excitation of the acrylate a 1,5-HAT results in a 1,4-diradical which forms the cyclobutene. Diastereoselectivities up to >20:1 were observed for the ring-closure reaction.

Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes

A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.

Tuning Flavin-Based Photocatalytic Systems for Application in the Mild Chemoselective Aerobic Oxidation of Benzylic Substrates

New flavin-based photocatalytic systems used for chemoselective aerobic visible-light oxidations have been developed by tuning the flavin structure and reaction conditions. 1,3-Dimethyl-7-trifluoromethylalloxazine (2) and 10-butyl-3-methyl-7-trifluoromethylisoalloxazine (3) were shown to mediate the selective oxidation of benzyl alcohols to form aldehydes in the presence of Cs2CO3. Flavin 3 was superior in the oxidation of toluene derivatives to form aldehydes in the presence of trifluoroacetic acid. On the other hand, photooxidations provided by ethylene-bridged quaternary flavinium salt 1 gave the corresponding carboxylic acids. The usefulness of the developed catalytic systems using 1–3 was also demonstrated in the oxidation of secondary benzylic and aliphatic alcohols, and benzylic methylene groups to form the corresponding ketones. The systems have the advantage of a broad substrate scope and metal-free conditions, which distinguish them from the previously reported flavin photooxidation reactions.

Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling

A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

Atropoenantioselective redox-neutral amination of biaryl compounds through borrowing hydrogen and dynamic kinetic resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME

The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R1 to R8, and R11 to R20 are as defined in the specification.

Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution

The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.

Pd(0)-catalyzed intramolecular Heck reaction: A general route for fused oxepine derivatives

A simple and facile approach for the synthesis of various structurally different tricyclic bent oxepine frameworks from a readily accessible precursor has been introduced. The synthesis of substituted oxepine derivative involved Pd(0)-catalyzed Heck reaction. This methodology enriches the literature for the large ring formation.