Tetralin

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Tetralin
Tetralin vial by NurdRage.jpg
Tetralin used in the production of potassium metal via catalyzed magnesium reduction
Names
IUPAC name
1,2,3,4-Tetrahydronaphthalene
Other names
Bacticin
Benzocyclohexane
Naphthalene 1,2,3,4-tetrahydride
THN
Identifiers
Jmol-3D images Image
Properties
C10H12
Molar mass 132.21 g/mol
Appearance Colorless liquid
Odor Naphtalene-like
Density 0.970 g/cm3 (at 20 °C)
Melting point −35.8 °C (−32.4 °F; 237.3 K)
Boiling point 207.6 °C (405.7 °F; 480.8 K)
Insoluble
Solubility Miscible with acetone, benzene, butanol, chloroform, decalin, ethanol, isopropanol, petroleum ether, toluene
Soluble in aniline, diethyl ether, methanol (50% w/w)
Hazards
Safety data sheet MATHESON TRI-GAS
Flash point 77 °C
Related compounds
Related compounds
Naphthalene
Decalin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetralin (IUPAC name 1,2,3,4-tetrahydronaphthalene) is an organic compound, a hydrocarbon having the chemical formula C10H12. It is similar to naphthalene in structure, except one ring is saturated.

Properties

Chemical

The reaction of elemental bromine with tetralin will give dry hydrogen bromide gas:

C10H12 + 4 Br2 → C10H8Br4 + 4 HBr ↑

Iodine will give hydrogen iodide.

Physical

Tetralin is a colorless viscous liquid, with a faint naphthalene-like smell. It is insoluble in water, but miscible with many organic solvents.

Availability

Tetralin can be purchased from chemical suppliers.

Preparation

There are several ways to prepare Tetralin.

The most convenient route involves the partial hydrogenation of naphthalene with a platinum catalyst. Small amounts of side products, such as decalin are also produced.

Birch reduction of naphthalene is another route, however the reaction is not selective and is a dangerous and time-consuming method.

Projects

Handling

Safety

Tetralin is irritant and should be handled with care. With a flash point of 77 °C, it is not very flammable and unless heated prior, it doesn't pose a fire hazard.

Storage

In closed air-tight bottles. Since it may form peroxides in contact with air, it's best to test it for peroxides every few months.

Disposal

Should be mixed with a more flammable solvent and burned.

References

Relevant Sciencemadness threads