20717-79-7

Usage

Uses

Used in Pharmaceutical and Chemical Industries:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Binaphthyl-based amino acids and amino alcohols via domino coupling reactions and lactam ring opening of intermediates. This application is crucial for the development of chiral molecules with potential pharmaceutical applications.
Used in Heterocyclic Chemistry:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Benzimidazoles and Benzimidazolequinone derivatives via cyclocondensation. These heterocyclic compounds are important in the development of pharmaceuticals, agrochemicals, and other organic compounds.
Used in Chiral Compounds Synthesis:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Axially chiral biaryls via Suzuki-Miyaura reactions. Axially chiral biaryls are valuable building blocks in the creation of enantioselective catalysts and ligands.
Used in Organic Synthesis:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Aryl ring-fused benzimidazolequinones via radical cyclization. These compounds have potential applications in various fields, including materials science and medicinal chemistry.
Used in Enzyme Research:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Probes for human cytochrome P450 enzymes. These probes are essential for studying enzyme activity and understanding the metabolism of various compounds.
Used in Organic Synthesis:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Phananthridinone derivatives via domino coupling reactions. These derivatives have potential applications in the development of novel organic compounds and materials.

InChI:InChI=1/C11H7BrO2/c12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h1-6H,(H,13,14)

Upstream product

• 3378-82-3 1-bromo-2-naphthaldehyde 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 76635-70-6 (1-bromo-2-naphthyl)methanol 
• 37763-43-2 1-bromo-2-(bromomethyl)naphthalene 
• 91-57-6 2-Methylnaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 
• 127349-02-4 1-bromo-2-(dibromomethyl)naphthalene 
• 20176-08-3 1-bromo-2-naphthalenyl-2-carbonitrile 
• 87262-94-0 1-bromo-2-(acetoxymethyl)naphthalene 

Downstream Products

• 89555-39-5 methyl 1-bromo-2-naphthalenecarboxylate 
• 138435-64-0 3,5-dimethoxyphenyl 1-bromo-2-naphthoate 
• 138435-68-4 3,5-diisopropylphenyl 1-bromo-2-naphthoate 
• 138435-69-5 3,5-di-tert-butylphenyl 1-bromo-2-naphthoate 
• 138435-67-3 3,5-diethylphenyl 1-bromo-2-naphthoate 
• 138435-65-1 3,5-dioctoxyphenyl 1-bromo-2-naphthoate 
• 138435-66-2 1-bromo-2-naphthoic acid(3,5-dimethylphenyl) ester 
• 54245-30-6 1-Hydroxy-2-naphthalincarbonsaeureethylester 
• 85464-88-6 [1,1']binaphthyl-2,2'-dicarboxylic acid dimethyl ester 
• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 1221726-55-1 1-bromo-N-(4-methoxybenzyl)-2-naphthamide 
• 1221726-56-2 3-(p-methoxybenzyl)dibenzo[a,k]phenanthridin-4(3H)-one 

Relevant academic research and scientific papers

Synthesis and cytotoxic activity of acronycine analogues in the benzo[c]pyrano[3,2-h]acridin-7-one and naphtho[1,2-b][1,7] and [1,10]-phenanthrolin-7(14H)-one series

Condensation of 1-bromo-2-naphthalenecarboxylic acid (9) with 7-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamine (13) followed by acid-mediated cyclization afforded 6-methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2- h]acridin-7-one (15), which was further methylated into 6-methoxy-3,3,14- trimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2-h]acridin-7-one (benzo[c]acronycine) (3) and 6,7-dimethoxy-3,3-dimethyl-3H-benzo[c]pyrano[3,2-h] acridine (4). Osmium tetroxide oxidation of 15 gave the (±)-cis-diol 16, which afforded the benzopyranoacridine and benzopyranoacridone esters 17-22 upon acylation. Condensation of 9 with suitable aminoquinolines 23-25 afforded the carboxylic naphthylquinolylamines 26-28. Cyclization gave the corresponding naphtho[1,2-b][1,10]-phenanthrolin-7(14H)-ones 29 and 30, and naphtho[1,2-b][1,7]-phenanthrolin-7(14H)-one 31, which were subsequently N-methylated to the desired 14-methylnaphtho[1,2-b][1,10] and [1,7]-phenanthrolinones 6, 7, and 8. Benzo[c]pyrano[3,2-h]acridin-7-one derivatives 3, 16, and 22 displayed cytotoxic activities within the same range of magnitude as acronycine itself, whereas 7-alkoxybenzo[c]pyrano[3,2-h]acridine and 7-acyloxybenzo[c]pyrano[3,2-h]acridine derivatives 4 and 17-21 were less active when tested against L1210 murine leukemia cells in vitro. Naphthophenanthrolinones 6-8 were devoid of significant antiproliferative activity, but compounds 29-31 bearing no substituent on the nitrogen atom at position 14 were more potent.

Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids

A mild and metal-free procedure is reported for the aerobic oxidation of substituted toluenes to carboxylic acids by using CBr 4 as initiator under irradiation from a 400 nm blue light-emitting diode.

Synthesis method of benzoic acid compounds

The invention discloses a photocatalytic oxidation synthesis method of benzoic acid compounds, and the photocatalytic oxidation synthesis method comprises the following specific steps: mixing and dissolving toluene compounds and a catalyst in a solvent, reacting for 24-60h in the presence of an oxidant under the conditions of 350-460 nm LED illumination and a temperature of 20-80 DEG C, and performing post-treatment on the reaction liquid to obtain the benzoic acid compounds. The photocatalytic oxidation synthesis method has the advantages of no need of metal catalysts, simple operation and mild reaction conditions; oxygen is used as an oxidant, and the photocatalytic oxidation synthesis method has high atom economy, cheap reagent and environmental protection. The photocatalytic oxidationsynthesis method has good substrate applicability, and various substituents can realize the synthesis of corresponding benzoic acid compounds.

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.

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.

Synthesis method of axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid

The invention relates to the technical field of bromination, hydrolysis, oxidation and coupling reaction in organic synthesis, particularly a synthesis method of an axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method comprises the following steps: synthesizing a compound 1-bromo-2-methylnaphthalene from an initial raw material 2-bromomethylnaphthalene, carrying out bromination, hydrolysis and oxidation on the 1-bromo-2-methylnaphthalene to obtain 1-bromo-2-naphthoic acid, generating an ester under the actions of methanol and thionyl chloride, protecting the carboxyl group, carrying out Ullmann reaction under the action of copper powder to perform coupling, carrying out hydrolysis to obtain 2,2'-dinaphthyl-1,1'-dicarboxylic acid, and finally, resolving to obtain the (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method is simple to operate, and has the advantages of higher yield and favorable economical efficiency.

Selenium-catalyzed C(sp3)-H acyloxylation: Application in the expedient synthesis of isobenzofuranones

Oxidative Se-catalyzed C(sp3)-H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho-allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural products.

Design and synthesis of new stable fluorenyl-based radicals

Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.

New fluorescent blue oled host and dopant materials based on the spirobenzofluorene

New spiro[benzo[c]fluorene-7,9'-fluorene] (SBFF)-based blue host materials, 9-phenyl-SBFF (BH-4P) and 5,9-diphenyl-SBFF (BH-6DP), were successfully prepared by spiro-formation of 9-phenyl-7H-benzo[c]fluoren- 7-one with 2-bromobiphenyl via lithiation and reaction of 5,9-dibromo-SBFF with phenylboronic acid through the Suzuki reaction, respectively. Diphenyl-[4-(2-[1,1;4,1]terphenyl-4-yl-vinyl)-phenyl]-amine (BD-1) and N,N-diphenyl-N',N'-diphenyl-SBFF-5,9-diamine (BD-6DPA) were used as dopant materials. Blue OLEDs with the configuration ITO/N,N'-bis-[4-(di-m-tolylamino) phenyl]-N,N'-diphenylbiphenyl-4,4'-diamine (DNTPD)/ bis[N-(1-naphthyl)-N-phenyl] benzidine (NPB)/host:5% dopant/SFC-137/Al-LiF were prepared from the two host materials doped with BD-1 and BD-6DPA dopants and the devices composed of BH-4P and BH-6DP doped with BD-6DPA showed blue EL spectra at 458 and 463 nm at 7 V and luminance efficiencies of 4.58 and 4.88 cd/A, respectively.