51114-70-6

Usage

Uses

Used in Pharmaceutical Synthesis:
1(2H)-Naphthalenone, 2,2-dibromo-3,4-dihydrois utilized as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows for the creation of a wide range of medicinal compounds, contributing to the development of novel treatments and therapies.
Used in Organic Compound Synthesis:
This chemical compound is also employed in the synthesis of other organic compounds, showcasing its versatility in the field of chemistry. Its ability to form various chemical bonds and reactions makes it a valuable asset in the development of new organic substances.
Used in Dye Manufacturing:
1(2H)-Naphthalenone, 2,2-dibromo-3,4-dihydroplays a significant role in the manufacturing process of dyes. Its chemical properties enable the production of a diverse array of dye colors, catering to the needs of various industries such as textiles, plastics, and printing.
Environmental Considerations:
Given the compound's toxicity to aquatic organisms and potential for causing long-term adverse effects on the aquatic environment, it is crucial to handle and dispose of 1(2H)-Naphthalenone, 2,2-dibromo-3,4-dihydrowith care. Proper safety measures and disposal methods should be implemented to minimize its impact on the environment and ensure the sustainability of aquatic ecosystems.

InChI:InChI=1/C10H8Br2O/c11-10(12)6-5-7-3-1-2-4-8(7)9(10)13/h1-4H,5-6H2

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 3349-64-2 1-tetralone oxime 
• 447-53-0 1,2-Dihydronaphthalene 

Downstream Products

• 90-15-3 α-naphthol 
• 771-15-3 2-bromo-1-naphthol 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1056246-70-8 2-bromo-1-tetralone 
• 1240493-84-8 2,3:8,9-dibenzo-12-phenyldispiro[4.0.5.1]dodeca-2,8-diene-1,4,7-trione 

Relevant academic research and scientific papers

N-Methylpyrrolidin-2-one hydrotribromide (MPHT) a mild reagent for selective bromination of carbonyl compounds: Synthesis of substituted 2-bromo-1-naphtols

The reaction of the N-methylpyrrolidin-2-one hydrotribromide complex (MPHT) with substituted-1-tetralones has been investigated. This safety reagent proved to be successful for selective α,α-dibromination of tetralones. Moreover, under base-free conditions, several 2-bromo-1-naphtols were obtained from tetralones in a 'one pot' sequence in good to excellent yields.

Preparation method of alpha, alpha-dibromoketone

The invention belongs to the field of preparation of fine chemical products and synthesis of pharmaceutical intermediates and relates to a preparation method of novel alpha, alpha-dibromoketone, in particular to a method for converting olefin into alpha, alpha-dibromoketone by use of dibromohydantoin or N-bromosuccinimide. Compared with the reported methods, the method has the advantages that rawmaterials are easy to obtain and low in cost, used reagents have smaller toxicity, and the method has greater cost and environmental protection advantages and wide application prospects.

One-pot syntheses of α,α-dibromoacetophenones from aromatic alkenes with 1,3-dibromo-5,5-dimethylhydantoin

A novel method for the preparation of α,α-dibromoacetophenones from aromatic alkenes was reported. This procedure was mediated by 1,3-dibromo-5,5-dimethylhydantoin, which served as bifunctional reagent, proceeding oxidation and bromination in one-pot.

Synthesis of dibromo ketones by the reaction of the environmentally benign H2O2-HBr system with oximes

It was found that oximes undergo deoximation in the presence of the H2O2aq-HBraq system to form ketones and bromo ketones. This reaction provided the basis for the synthesis of dibromo ketones in yields varying from 40% to 94%. This method is environmentally friendly, sustainable, and easy to perform. The results of this investigation extend the potential of the use of oximes for the protection of carbonyl group, thus offering the ability to perform not only conventional deoximation but also the subsequent bromination of ketones. The reaction is easily scaled up and dibromo ketones can be prepared in gram amounts. Versita Sp. z o.o.

Visible-light photoredox catalysis: Dehalogenation of vicinal dibromo-, α-halo-, and α,α-dibromocarbonyl compounds

vic-Dibromo-, α-halo-, or α,α-dibromocarbonyl compounds can be efficiently dehalogenated using catalytic tris(2,2′-bipyridyl) ruthenium dichloride (Ru(bpy)3Cl2) in combination with 1,5-dimethoxynaphthalene (DMN) and ascorbate as sacrificial electron donor. For this process, a visible light promoted photocatalytic cycle is proposed that involves the reduction of carbon halogen bonds via free radical intermediates.

Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions

Several aryl substituted ketones, cyclic ketones, 1,3-diketones and a β-ketoamide were halogenated with N-halosuccinimides under solvent-free reaction conditions (SFRC) at various temperatures (20-80 °C), whereas less enolized ketones required the presence of an acid catalyst (p-toluenesulfonic acid, PTSA). Bromination of substituted acetophenones obeys first order kinetics v=kBr[ketone] and the following correlation with the keto-enol equilibrium constant: log kBr=0.3pKE+C1, less enolized substrates being more reactive; the moderate positive charge developed in the rate determining step was confirmed by the Hammett correlation (ρ=-0.5). On the other hand, in cyclic ketones an opposite relation was observed: log kBr=-0.6pKE+C2, indicating higher reactivity of substrates with higher enolization constant (KE). The important role of the nature of the solvent (MeCN, MeOH) in preorganization of the ketone-NBS-PTSA mixture prior to SFRC bromination was found.

A convenient synthesis of 2,2-dibromo-1-arylethanones by bromination of 1-arylethanones with the H2O2-HBr system

1-Arylethanones and related compounds are brominated in dioxane with the H2O2-HBraq system, resulting in the replacement of two hydrogen atoms in the methyl group with bromine. The reaction is also accompanied by bromination of the aromatic ring provided that the latter contains electron-donating substituents. The reaction proceeds rapidly (20 min) and results in complete conversion of ketones to give 2,2-dibromo-1- arylethanones in yields up to 86%. Georg Thieme Verlag Stuttgart.

α-BROMINATION OF KETONES WITH THE BROMINE COMPLEX OF POLY(STYRENE-CO-4-VINYLPYRIDINE)

The bromine complex of poly(styrene-co-4-vinylpyridine) reacted with ketones and 1,3-diketones to form α-bromo or α,α-dibromo products in high yields.