Tetralin

Tetralin

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
SMILES c1ccc2c(c1)CCCC2
Properties
Chemical formula	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)
Solubility in water	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	Sigma-Aldrich
Flash point	77 °C (170.6 °F; 350 K)
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 ↑

If iodine is used, the reaction 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, like alcohols.

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. Birch reduction is also a dangerous and time-consuming method.

Projects

• Maky dry HBr and HI gas
• Preparation of elemental potassium

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

• Preparation of Tetralin?
• Catalyzed Hydrogenation of Naphthalene to Tetralin