1-Bromonaphthalene is an organic compound with the formula C10H7Br. It is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene. Under normal conditions, the substance is a colorless liquid.
Synthesis and reactions It is prepared by treatment of naphthalene with bromine: C10H8 + Br2 → C10H7Br + HBr
The compound exhibits many reactions typical of aryl bromides. Bromide can be displaced by cyanide to give the nitrile.
It forms a Grignard reagent and organolithium compound.
Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by lithium–halogen exchange: C10H7Br + BuLi → C10H7Li + BuBr (Bu = butyl) The resulting 1-lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. The 1,8-dilithio derivative is a precursor to a host of peri-naphthalene derivatives.
Applications The compound is also used as a precursor to various substituted naphthalenes, but substituted bromonaphthalenes are more important commercially..
Because of its high refractive index (1.656-1.659nD), 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.
See also 2-Bromonaphthalene 1-Chloronaphthalene 1-Fluoronaphthalene
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