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Structural formula of 1-tetralone
Ball-and-stick model of the 1-tetralone molecule
IUPAC name
Other names
α-Tetralone; 1-Tetralone
3D model (JSmol)
ECHA InfoCard 100.007.692
Molar mass 146.189 g·mol−1
Appearance colorless liquid
Density * 1.099 g·cm−3 (25 °C)[1]
Melting point 2–7 °C[1]
Boiling point * 255–257 °C[2]
  • 113–116 °C (8 hPa)[1]
Solubility soluble in organic solvents
Vapor pressure 2.7 Pa (20 °C)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor.[4] It is used as starting material for agricultural and pharmaceutical agents. The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.[5]


By oxidation of 1,2,3,4-tetrahydronaphthalene[edit]

As already described in 1933 by Heinrich Hock, 1,2,3,4-tetrahydronaphthalene tends to autoxidize and gradually forms the 1-hydroperoxide with atmospheric oxygen.[6] The heavy metal ion catalyzed air oxidation of 1,2,3,4-tetrahydronaphthalene with Cr3+[7] or Cu2+ in the liquid phase leads via the hydroperoxide to a mixture of the intermediate 1-tetralol and the final product 1-tetralone.[8]

Oxidation von Tetraloin zu 1-Tetralon

The boiling points of the main component 1-tetralone (255-257 °C) and the minor component 1-tetralol (255 °C)[2] are virtually identical, the latter is therefore removed by a chemical reaction.[9]

By Friedel-Crafts reactions[edit]

The starting compound 4-phenylbutanoic acid (whose sodium salt sodium phenylbutyrate is used to treat hyperammonaemia) is accessible from 3-benzoylpropanoic acid via catalytic hydrogenation, using a palladium contact catalyst.[4] 3-Benzoylpropanoic acid[10] itself can be obtained by a Haworth reaction (a variant of the Friedel-Crafts reaction) from benzene and succinic anhydride .

The intramolecular cyclization of 4-phenylbutanoic acid to 1-tetralone is catalyzed by polyphosphoric acid[4] and methanesulfonic acid.[11]

Cyclisierung von 4-Phenylbuttersäure zu 1-Tetralon

It has been described as a teaching experiment for chemistry lessons.[12] 4-Phenylbutanoic acid can also be quantitatively converted into 1-tetralone by heating in the presence of a strong Lewis acid catalyst such as bismuth(III)bis(trifluoromethanesulfonyl)amide[13] [Bi(NTf2)3], which is relatively easily accessible.[14]

The use of the acid chloride and tin(IV) chloride (SnCl4) allows significantly shorter reaction times than the Friedel-Crafts acylation with 4-phenylbutanoic acid.[9]

Synthese von 1-Tetralon über 4-Phenylbuttersäurechlorid

4-Phenylbutanoic acid chlorides with electron-donating groups can be cyclized to 1-tetralones under mild reaction conditions in yields greater than 90% using the strong hydrogen-bonding solvent hexafluoroisopropanol (HFIP).[15]

The AlCl3-catalyzed acylation of benzene with γ-butyrolactone produces 1-tetralone.[9]

Synthesis of 1-tetralone using butyrolactone.


1-Tetralone can be reduced via a Birch reduction with lithium in liquid ammonia to 1,2,3,4-tetrahydronaphthalene.[16] The keto group can also be reduced to a secondary alcohol giving 1-tetralol, when a modified process is applied, using the addition of aqueous ammonium chloride solution after evaporation of the ammonia.[17]

Reaktionen von 1-Tetralon mit Li in Ammoniak

With calcium in liquid ammonia, 1-tetralone is reduced to 1-tetralol at -33 °C in 81% yield.[18]

The methylene group in α-position to the keto group is particularly reactive and can be converted with formaldehyde (in the form of the trimeric trioxane) to 2-methylene-1-tetralone in the presence of the trifluoroacetic acid salt of N-methylaniline with yields up to 91% .

Synthese von 2-Methylen-1-tetralon aus 1-Tetralon

The 2-methylene ketone is stable at temperatures below -5 °C, but fully polymerizes at room temperature within 12 hours.[19]

In the Pfitzinger reaction of 1-tetralone with isatin, a compound called tetrofan (3,4-dihydro-1,2-benzacridine-5-carboxylic acid) is formed.

Synthese von Tetrophan

The reactivity of the α-methylene group is also exploited in the reaction of 1-tetralone with methanol at 270-290 °C, which produces via dehydrogenation and formation of the aromatic naphthalene ring system 2-methyl-1-naphthol in 66% yield.[20]

Synthese von 2-Methyl-1-naphthol

The oxime of 1-tetralone reacts with acetic anhydride leading to aromatization of the cycloalkanone ring. The resulting N-(1-naphthyl)acetamide[21] has biological properties akin to those of 2-(1-Naphthyl)acetic acid as a synthetic auxin.

Synthese von N-(1-Naphthyl)acetamid

The tertiary alcohol formed in the Grignard reaction of 1-tetralone with phenylmagnesium bromide reacts with acetic anhydride upon elimination of water to 1-phenyl-3,4-dihydronaphthalene, which is dehydrated with elemental sulfur in an overall yield of about 45% to 1-phenylnaphthalene.[22]

Synthese von 1-Phenylnaphthalin aus 1-Tetralon

The ruthenium(II)-catalyzed arylation of 1-tetralone using phenyl boronic acid neopentyl glycol ester gives 8-phenyl-1-tetralone in up to 86% yield.[23]

Synthese von 8-Phenyl-1-tetralon aus 1-Tetralon

With 5-aminotetrazole and an aromatic aldehyde, 1-tetralone reacts in a multi-component reaction under microwave irradiation to form a four-membered heterocyclic ring system.[24]

Multikomponentenreaktion von 1-Tetralon mit Aminotetrazol und aromatischem Aldehyd


By far the most important application of 1-tetralone is in the synthesis of 1-naphthol by aromatization, e.g. upon contact with platinum catalysts at 200 to 450 °C.[25]

Synthese von 1-Naphthol aus 1-Tetralon

1-Naphthol is the starting material for the insecticides carbaryl and the beta-blockers propranolol.


Toxicological studies were dermally performed with rabbits, with an LD50 of 2192 mg·kg−1 body weight being observed.[1]


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