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Usage

Uses

Used in Chemical Synthesis Industry:
1,3-Dibromonaphthalene is utilized as an intermediate in the synthesis of various chemicals and dyes, playing a crucial role in the production of a range of compounds that find applications in different sectors.
Used in Organic Synthesis:
As a building block in organic synthesis, 1,3-Dibromonaphthalene is employed in the preparation of other aromatic compounds, contributing to the development of new materials and substances with specific properties for various applications.

Upstream product

• 20191-76-8 2,4-dibromo-1-naphthylamine 
• 19922-78-2 1,2,3,4-tetrabromo-1,2,3,4-tetrahydronaphthalene 
• 91-20-3 naphthalene 
• 7499-65-2 4-bromo-2-nitronaphthalene 
• 74924-94-0 4-bromonaphthalene-2-amine 

Downstream Products

• 111181-01-2 5-bromobenzcarbazole 

Relevant academic research and scientific papers

Halogen bonds of iodonium ions: A world dissimilar to silver coordination

A distinct difference between the three-center halogen bond and the analogous three-center coordinative bond of silver is demonstrated by computational, X-ray crystallographic and solution NMR spectroscopic investigations of their complexes with a bidentate Lewis base. Iodine(I) preferentially forms an entropically favored monomeric complex, whereas silver(I) forms enthalpically favored dimeric complexes. Counterion coordination considerably influences the structure of the silver complexes in the solution and solid state, whereas it does not have notable effect on the analogous halogen bond.

Selective bromination of 1-bromonaphthalene: Efficient synthesis of bromonaphthalene derivatives

Selective and specific preparation methods are described for 1,4-dibromonaphthalene, 1,5-dibromonaphthalene and 1,3,5-tribromonaphthalene. The reaction of 1-bromonaphthalene and naphthalene with stoichometric quantities of bromine by using a minimum amount of solvent (methylene chloride) at -30 and -50°C smoothly affords 1,4-dibromonaphthalene in 90% yield. Photobromination of 1-bromonaphthalene in CCl4 at -30°C gives 1,2,3,4,5-pentabromo-1,2,3,4-tetrahydronaphthalenes, whereas 1,5-dibromonaphthalene is obtained at reflux (77°C) in 80% yield under the same conditions. Dehydrobromination of the pentabromide by t-BuOK affords 1,3,5-tribromonaphthalene as a sole product (91%). 1,5-Dibromo- and 1,3,5-tribromonaphthalenes were efficiently converted to the corresponding methoxy naphthalene derivatives.

Bromination of naphthalene. Preparation of 1,3-dibromonaphthalene

Photobromination of naphthalene with molecular bromine gives only one stereoisomer α,2β,3α,4β-tetrabromo-1,2,3,4-tetrahydronaphthalene (yield 90%); dehydrobromination of which results in the formation of 1,3- dibromonaphthalene in 88% yield.

Bromination of naphthalene and derivatives: High temperature bromination XI

Thermal and photobromination of naphthalene and derivatives have been studied. Several hexabromo- (12, 13, 16 and 17), and tetrabromotetralin derivatives (23, 24, and 25) have been obtained as the major products, besides bromonaphthalene derivatives. Base-promoted elimination reactions of 12, 13, 16 and 17 provided di- (8) tri- (10) and tetrabromo-naphthalenes (22). A convenient method was developed for the synthesis of 1,3- dibromonaphthalene (26) starting from (24). The structures of these products were determined by 1H-,13C- NMR data and X-ray structural analysis.