3401-47-6

Usage

Uses

1. Used in Chemical Synthesis:
1-Bromo-2-methoxynaphthalene is used as a reagent for the synthesis of a catalyst that is highly enantioselective for aziridination of styrene derivatives. This application is significant in the pharmaceutical industry, as it helps in the production of chiral drugs with improved efficacy and reduced side effects.
2. Used in Catalyst Preparation:
In the field of catalysis, 1-Bromo-2-methoxynaphthalene is utilized to prepare catalysts that are essential for various chemical reactions. These catalysts play a crucial role in enhancing the efficiency and selectivity of the reactions, leading to the production of desired products with minimal side reactions.
3. Used in the Synthesis of Biaryls and Biheterocycles:
1-Bromo-2-methoxynaphthalene is also employed in the preparation of biaryls and biheterocycles through palladium-catalyzed Ullmann coupling. This application is particularly relevant in the synthesis of complex organic molecules, which are often found in pharmaceuticals, agrochemicals, and advanced materials.
4. Used in the Pharmaceutical Industry:
As a synthetic intermediate, 1-Bromo-2-methoxynaphthalene can be used to develop new pharmaceutical compounds with potential therapeutic applications. Its unique structure allows for the creation of novel molecules that can target specific biological pathways, leading to the development of more effective drugs.
5. Used in the Agrochemical Industry:
In the agrochemical sector, 1-Bromo-2-methoxynaphthalene can be used to synthesize new compounds with pesticidal, herbicidal, or fungicidal properties. These compounds can be employed to protect crops from pests and diseases, ensuring higher yields and better quality produce.
6. Used in the Development of Advanced Materials:
The unique structure of 1-Bromo-2-methoxynaphthalene also makes it a promising candidate for the development of advanced materials with specific properties, such as optoelectronic devices, sensors, and energy storage systems. Its versatility in chemical reactions allows for the creation of novel materials with tailored properties for various applications.

InChI:InChI=1/C11H9BrO/c1-13-10-7-6-8-4-2-3-5-9(8)11(10)12/h2-7H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 93-04-9 2-Methoxynaphthalene 
• 7072-23-3 1,3-dibromo-5,5-dimethyl-hydantoin 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 7789-69-7 phosphorus pentabromide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 135-19-3 β-naphthol 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 573-97-7 1-bromo-2-naphthol 
• 32721-21-4 1-iodo-2-methoxynapthalene 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 947-62-6 2-methoxy-1-naphthoic acid 
• 108979-03-9 (2-methoxynaphthalen-1-yl)(phenyl)sulfane 
• 111064-96-1 (2-methoxynaphthalen-1-yl)(p-tolyl)sulfane 
• 2246-42-6 2-methoxynaphthylamine 
• 39191-42-9 N-(2-methoxy-[1]naphthyl)-anthranilic acid 
• 95854-85-6 2-(2-methoxy-1-naphthylthio)benzoic acid 
• 883-62-5 3-methoxy-2-naphthoic acid 
• 93-04-9 2-Methoxynaphthalene 
• 77003-52-2 C₃₃H₂₆O₃ 
• 573-97-7 1-bromo-2-naphthol 
• 84167-74-8 5-bromo-6-methoxy-2-acetylnaphthalene 
• 186465-05-4 1-([1,1'-biphenyl]-2-yl)-2-methoxynaphthalene 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 1130-80-9 2-methoxy-1-methylnaphthalene 

Relevant academic research and scientific papers

Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds

4-Methoxy-1H-phenalen-1-one (4-methoxyperinaphthenone, 1), a subunit found in some Musa phytoalexins and related natural products from the Haemodoraceae, was synthesized starting from 2-methoxynaphthalene in five steps and an overall yield of 36%. A Heck-Fujiwara coupling between ethyl acrylate and 1-bromonaphthalene afforded the corresponding (E)-naphthylpropanoic acid which, after hydrogenolysis, was subjected to a one-pot Friedel-Crafts acylation-DDQ dehydrogenation procedure to furnish 1.

Cetyltrimethylammonium bromide as an efficient catalyst for regioselective bromination of alkoxy naphthalenes with trimethyl benzyl ammonium tribromide: Synthetic and kinetic approach

Bromination of 2-alkoxynaphthalene (2-ANP) and its derivatives with trimethyl benzyl ammonium tribromide (TMBATB) did not proceed smoothly even under reflux conditions. But the addition of microconcentrations of cetyltrimethyl ammonium bromide (CTAB) to t

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.

Bromination of phenyl ether and other aromatics with bromoisobutyrate and dimethyl sulfoxide

Bromoisobutyrate has been used for the first time as a general brominating source for the direct bromination of a diverse of simple phenyl ethers. Aromatic ethers bearing various substituents could be compatible in this reaction system delivering brominated arenes in moderate to good yields. The reaction system can also be expanded to bromination of phenols and unactivated arene. This process can be regarded as an alternative for the well-established bromination systems for bromoarene synthesis.

Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones

We describe the first atropselective Suzuki-Miyaura cross-coupling of β-keto enol triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual intramolecular Morita-Baylis-Hillman reaction is utilized for the Z-selective synthesis of β-keto enol triflates.

Axially Chiral 1,1'-Binaphthyl-2-Carboxylic Acid (BINA-Cox) as Ligands for Titanium-Catalyzed Asymmetric Hydroalkoxylation

Axially chiral, enantiopure 1,1'-binaphthyl-2-carboxylic acids (BINA-Cox) have recently been introduced as chiral ligands for transition metal catalysis. Together with equimolar, co-catalytic amounts of Ti(OiPr)4 and water they form an in situ catalyst that performs the asymmetric catalytic hydroalkoxylation of 2-allylphenols to 2-methylcoumarans at high temperature (240 °C, microwave heating). The synthesis of reference ligand 2'-MeO-BINA-Cox (L1) has been optimized and performed at molar scale. Synthetic routes have been developed to access a variety of substituted BINA-Cox ligands (>30 examples), which have been tested for ligand effects on the reference asymmetric cyclization of 2-allylphenol. The substrate range of asymmetric catalytic hydroalkoxylation has been explored through systematic substrate structure variations to define scope and limitations of the titanium-catalyzed process. The new substrates 2-(1-vinylcycloalkyl)phenols (1j, 1k), 2-(2-vinylphenyl)propan-2-ol (1t), and 2'-vinyl-[1,1'-biphenyl]-2-ol (1u) are shown to undergo asymmetric catalytic cyclization to benzodihydrofurans and benzo[c]chromene, respectively.

Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics

Alkoxyamide has been reported as a catalyst for the activation ofN-bromosuccinimide to perform bromocyclization and bromination of a wide range of substrates in a lipophilic solvent, where adequate suppression of the background reactions was observed. The key feature of the active site is the alkoxy group attached to the sulfonamide moiety, which facilitates the acceptance as well as the delivery of bromonium species from the bromine source to the substrates.

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

Electrocatalytic Deuteration of Halides with D2O as the Deuterium Source over a Copper Nanowire Arrays Cathode

Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D2O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross-coupling of carbon and deuterium free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C?H to C?D transformations were achieved with high yields and deuterium ratios through a one-pot halogenation–deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific deuterium incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chemicals with low energy input highlighted the potential practicality.