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

Chemical Properties

solid

Uses

1-Bromo-2-methoxy-naphthalene is a useful synthetic intermediate. It is used as a reagent to synthesize a catalyst for highly enantioselective aziridination of styrene derivatives. It can also be used to prepare biaryls or biheterocycles by palladium-catalyzed Ullmann coupling.

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

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 573-97-7 1-bromo-2-naphthol 
• 77-78-1 dimethyl sulfate 
• 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 
• 74-88-4 methyl iodide 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 7072-23-3 1,3-dibromo-5,5-dimethyl-hydantoin 
• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 5392-12-1 2-methoxy-1-naphthaldehyde 

Downstream Products

• 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 
• 186465-05-4 1-([1,1'-biphenyl]-2-yl)-2-methoxynaphthalene 
• 573-97-7 1-bromo-2-naphthol 
• 1130-80-9 2-methoxy-1-methylnaphthalene 
• 17295-03-3 1-ethyl-2-methoxynaphthalene 
• 29574-51-4 6,6-dimethyl-6H-dibenzopyran 
• 93-04-9 2-Methoxynaphthalene 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 

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.