1-Bromonaphthalene
Chemical compound
From Wikipedia, the free encyclopedia
1-Bromonaphthalene is an organic compound with the formula C10H7Br.
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| Names | |
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| Preferred IUPAC name
1-Bromonaphthalene | |
| Other names
α-Bromonaphthalene | |
| 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 | 207.070 g·molâ1 |
| Appearance | Colorless liquid |
| Density | 1.48 g/mL |
| Melting point | 1â2 °C (34â36 °F; 274â275 K) |
| Boiling point | 132â135 °C at 12 mm; 145â148 °C at 20 mm |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 â 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.
Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by lithiumâhalogen exchange:
- C10H7Br + BuLi â 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.[3]
Applications
The compound is also used as a precursor to various substituted naphthalenes, but substituted bromonaphthalenes are more important commercially.[4]
Because of its high refractive index (1.656-1.659nD),[5] 1-bromonaphthalene is used as an embedding agent in microscopy and for determining the refraction of crystals.