1-Bromonaphthalene

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.

1-Bromonaphthalene

Names
Preferred IUPAC name 1-Bromonaphthalene
Other names α-Bromonaphthalene
Identifiers
CAS Number	90-11-9^Y
3D model (JSmol)	Interactive image
ChemSpider	6735
ECHA InfoCard	100.001.787
EC Number	201-965-2
MeSH	C108222
PubChem CID	7001
UNII	976Y53P08P^Y
CompTox Dashboard (EPA)	DTXSID30861681
InChI InChI=1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H Key: DLKQHBOKULLWDQ-UHFFFAOYSA-N InChI=1/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H Key: DLKQHBOKULLWDQ-UHFFFAOYAA
SMILES c1ccc2c(c1)cccc2Br
Properties
Chemical formula	C10H7Br
Molar mass	207.07
Appearance	colorless liquid
Density	1.48 g/mL
Melting point	1-2 ºC
Boiling point	132–135 °C at 12 mm; 145–148 °C at 20 mm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 organolithiuim 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-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

References

1. H. T. Clarke and M. R. Brethen "α-Bromonaphthalene" Org. Synth. 1921, volume 1, 35. doi:10.15227/orgsyn.001.0035
2. Henry Gilman, Nina B. St. John, and F. Schulze "α-Naphthoic Acid" Org. Synth. 1931, volume 11, 80. doi:10.15227/orgsyn.011.0080