92455-04-4

Basic information

• Product Name: 6-BroMo-1-chloro-2-Methoxynaphthalene
• Synonyms: 6-BroMo-1-chloro-2-Methoxynaphthalene
• CAS NO: 92455-04-4
• Molecular Formula: C11H8BrClO
• Molecular Weight: 271.53762
• Mol File: 92455-04-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-BroMo-1-chloro-2-Methoxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BroMo-1-chloro-2-Methoxynaphthalene(92455-04-4)
• EPA Substance Registry System: 6-BroMo-1-chloro-2-Methoxynaphthalene(92455-04-4)

Safety Data

• Hazardous Substances Data: 92455-04-4(Hazardous Substances Data)

Usage

General Description

6-Bromo-1-chloro-2-methoxynaphthalene is a chemical compound with the molecular formula C11H8BrClO. It is a derivative of naphthalene and belongs to the family of brominated and chlorinated organic compounds. This chemical is used in the synthesis of pharmaceuticals and agrochemicals, as well as in the production of dyes and pigments. It is also a versatile building block for the creation of various other organic compounds. The compound's unique combination of bromine, chlorine, and methoxy functional groups makes it useful in a variety of chemical reactions and applications. However, it is important to handle this compound with caution, as it may pose health and environmental risks if not used properly.

Upstream product

• 102169-88-0 6-bromo-1-chloro-naphthalen-2-ol 
• 74-88-4 methyl iodide 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 247174-18-1 6-bromo-2-methoxynaphthalene-1-carbaldehyde 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 13101-92-3 1-chloro-2-methoxynaphthalene 

Downstream Products

• 102169-88-0 6-bromo-1-chloro-naphthalen-2-ol 

Relevant articles and documents

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system

A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.

A Doubly Biomimetic Synthetic Transformation: Catalytic Decarbonylation and Halogenation at Room Temperature by Vanadium Pentoxide

The halogenation of the C?H bond by metal-oxo-peroxo species and the decarbonylation of aldehydes by metal-peroxo species are performed routinely in biological systems. However, metal-mediated decarbonylative halogenation is unknown in nature. In this work, we have shown that widely available V2O5 and VO(acac)2 (acac=acetylacetonate) can catalyze decarbonylative halogenation through the generation of an intermediate vanadium-oxo-peroxo species, which was characterized by using 51 V NMR, UV/Vis, and resonance Raman spectroscopy. Further detection of formic acid from the reaction mixture confirmed the biomimetic aspects of decarbonylative halogenation. A detailed experimental and DFT study indicated a concerted mechanism for this decarbonylative halogenation performed under simple and mild reaction conditions.

Decarbonylative halogenation by a vanadium complex

Metal-catalyzed halogenation of the C-H bond and decarbonylation of aldehyde are conventionally done in nature. However, metal-mediated decarbonylative halogenation is unknown. We have developed the first metal-mediated decarbonylative halogenation reaction starting from the divanadium oxoperoxo complex K3V5+2(O 22-)4(O2-)2(μ-OH) (1). A concerted decarbonylative halogenation reaction was proposed based on experimental observations.