5467-58-3

Usage

Chemical Properties

Oil

Synthesis Reference(s)

The Journal of Organic Chemistry, 11, p. 399, 1946 DOI: 10.1021/jo01174a017

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

Upstream product

• 100-66-3 methoxybenzene 
• 2216-69-5 1-Methoxynaphthalene 

Downstream Products

• 163397-20-4 (1-methoxynaphthalen-4-yl)(phenyl)sulfane 
• 571-57-3 4-bromo-1-naphthol 
• 269410-16-4 2-(4-methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 2216-69-5 1-Methoxynaphthalene 
• 219834-95-4 (4-methoxynaphthalen-1-yl)boronic acid 
• 72774-00-6 1-methoxy-4-phenylnaphthalene 
• 36159-76-9 4-phenyl-1-naphthol 
• 1303519-19-8 1-methoxy-4-{3,5-(diphenyl)phenyl}naphthalene 
• 61639-32-5 1-ethynyl-4-methoxynaphthalene 
• 36831-92-2 2-(4-bromo-1-hydroxy-[2]naphthoyl)-benzoic acid 
• 38063-26-2 5-hydroxybenzophenanthrene 

Relevant academic research and scientific papers

Aerobic oxidative bromination of arenes using an ionic liquid as both the catalyst and the solvent

A method for the bromination of alkoxy-substituted benzenes and naphthalenes was developed by using the residual oxygen in the reaction tube as the oxidant, and [Bmim]NO3 (1-butyl-3-methylimidazolium nitrate) ionic liquid as both the catalyst and the solvent. No other reagent apart from the ionic liquid and molecular bromine was used in the reactions, and basically all the bromine atoms in the bromine source were transferred to the bromination products, showing that the presented protocol is highly atom economic and practical.

Selective Halogenation Using an Aniline Catalyst

Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.

An efficient and regioselective oxybromination of aromatic compounds using potassium bromide and oxone

A simple, efficient and regioselective method for oxybromination of aromatics is reported. The electrophilic substitution of bromine generated in situ from potassium bromide using oxone as an oxidant for the first time.