1,6-Dibromonaphthalene Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

InChI

InChI=1S/C10H6Br2/c11-8-4-5-9-7(6-8)2-1-3-10(9)12/h1-6H

InChIKey

PUIAXCYSKMFFOU-UHFFFAOYSA-N

SMILES

C1(Br)=C2C(C=C(Br)C=C2)=CC=C1

1,6-Dibromonaphthalene Usage And Synthesis

Chemical Properties

1,6-Dibromonaphthalene is a white crystalline solid that has two isomers.

Uses

1,6-Dibromonaphthalene is mainly used as a pharmaceutical intermediate. It can be used as a ligand for metal ions, such as copper, iron, and zinc. It has also been shown to have selectivities for unsymmetrical molecules with unmodified organic ligands.

Synthesis

Example 20: Preparation of Compound 50; [235] [236] 20-A. Preparation of Compound 20a; To a solution of 1,6-dihydroxynaphthalene (1.2 g, 7.68 mmol) in acetonitrile (50 mL) was added phosphorus tribromide (PBr3, 2.9 g, 10.8 mmol), and the mixture was heated and refluxed with stirring for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by the addition of methanol (100 mL) to precipitate the solid product. The solid was collected by filtration, washed well with methanol and dried under reduced pressure to afford compound 20a 1,6-dibromonaphthalene (1.6 g, 74% yield). [M] = 286

References

[1] Patent: WO2007/86695, 2007, A1. Location in patent: Page/Page column 76-77
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 267 - 273