1-Bromonaphthalene
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Preferred IUPAC name
1-Bromonaphthalene | |
Other names
α-Bromonaphthalene
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.001.787 |
EC Number |
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MeSH | C108222 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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 | |
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, (1.656-1.659nD) [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[]
References[]
- ^ H. T. Clarke and M. R. Brethen "α-Bromonaphthalene" Org. Synth. 1921, volume 1, 35. doi:10.15227/orgsyn.001.0035
- ^ Henry Gilman, Nina B. St. John, and F. Schulze "α-Naphthoic Acid" Org. Synth. 1931, volume 11, 80. doi:10.15227/orgsyn.011.0080
- ^ "1-Bromonaphthalene".
- Bromoarenes
- Naphthalenes
- Organobromides