1-Bromonaphthalene Explained

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:^[1]

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^[2] and organolithium compound. 1-Lithionaphthalene can be further lithiated to give 1,8-dilithionaphthalene, a precursor to peri-naphthalene compounds.

Applications

Because of its high refractive index (1.656-1.659_nD),^[3] 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.

The compound is also used as a precursor to various substituted derivatives of naphthalene.

See also

• 1-Chloronaphthalene
• 1-Fluoronaphthalene

Notes and References

1. 10.15227/orgsyn.001.0035. α-BROMONAPHTHALENE. Organic Syntheses. 1921. 1. 35.
2. 10.15227/orgsyn.011.0080. α-NAPHTHOIC ACID. Organic Syntheses. 1931. 11. 80.
3. Web site: 1-Bromonaphthalene.