3401-47-6

Basic information

• Product Name: 1-BROMO-2-METHOXYNAPHTHALENE
• Synonyms: 1-BROMO-2-METHOXYNAPHTHALENE;2-Methoxy-1-naphtyl bromide;1-Bromo-2-methoxynapthalene;Naphthalene, 1-broMo-2-Methoxy-;1-Bromo-2-methoxynaphthalene, >=97%
• CAS NO: 3401-47-6
• Molecular Formula: C₁₁H₉BrO
• Molecular Weight: 237.09
• EINECS: 222-272-1
• Product Categories: Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;C11;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 3401-47-6.mol
• Article Data: 77

Chemical Properties

• Melting Point: 80-83 °C
• Boiling Point: 319.248 °C at 760 mmHg
• Flash Point: 132.944 °C
• Appearance: /
• Density: 1.448 g/cm³
• Vapor Pressure: 0.000641mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• BRN: 2045600
• CAS DataBase Reference: 1-BROMO-2-METHOXYNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-METHOXYNAPHTHALENE(3401-47-6)
• EPA Substance Registry System: 1-BROMO-2-METHOXYNAPHTHALENE(3401-47-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3401-47-6(Hazardous Substances Data)

Usage

Description

1-Bromo-2-methoxynaphthalene is an organic compound that serves as a valuable synthetic intermediate in the field of chemistry. It is a solid with a molecular structure that features a naphthalene ring, a bromine atom, and a methoxy group. This unique combination of functional groups makes it a versatile compound for various chemical reactions and applications.

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 
• 573-97-7 1-bromo-2-naphthol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 7789-69-7 phosphorus pentabromide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 135-19-3 β-naphthol 
• 32721-21-4 1-iodo-2-methoxynapthalene 
• 5392-12-1 2-methoxy-1-naphthaldehyde 

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 
• 92643-16-8 6-Bromo-1-(chloromethyl)-2-methoxynaphthalene 
• 883-62-5 3-methoxy-2-naphthoic acid 
• 93-04-9 2-Methoxynaphthalene 
• 77003-52-2 C₃₃H₂₆O₃ 
• 138604-66-7 (1R)-menthyl (aS,1R)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylate 
• 23997-58-2 1-(2'-methoxyphenoxy)-2-methoxynaphtalene 
• 573-97-7 1-bromo-2-naphthol 
• 84167-74-8 5-bromo-6-methoxy-2-acetylnaphthalene 

Relevant articles and documents

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.

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.

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.

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.