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TETRALIN

Tetralin (1,2,3,4-tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12.
Tetralin is a partially hydrogenated derivative of naphthalene.
Tetralin is a colorless liquid that is used as a hydrogen-donor solvent.

CAS Number: 119-64-2
EC Number: 204-340-2
IUPAC Name: 1,2,3,4-Tetrahydronaphthalene
Chemical Formula: C10H12

Other names: 1,2,3,4-Tetrahydronaphthalene, TETRALIN, 119-64-2, Tetrahydronaphthalene, Benzocyclohexane, Bacticin, Naphthalene, 1,2,3,4-tetrahydro-, Tetraline, Tetranap, Tetralina, Naphthalene 1,2,3,4-tetrahydride, tetralene, Caswell No. 842A, CCRIS 3564, HSDB 127, UNII-FT6XMI58YQ, delta(sup 5,7,9)-naphthantriene, FT6XMI58YQ, EINECS 204-340-2, NSC 77451, EPA Pesticide Chemical Code 055901, DTXSID1026118, CHEBI:35008, AI3-01257, TETRALIN [HSDB], TETRALIN [MI], MFCD00001733, NSC-77451, TETRALIN [USP-RS], TETRALIN [WHO-DD], DTXCID306118, Naphthalene, tetrahydro-, .delta.(5,7,9)-Naphthantriene, 1,2,3,4-tetrahydro-naphthalene, EC 204-340-2, Naphthalene-1,2,3,4-tetrahydride, 68412-24-8, TETRALIN (USP-RS), Tetralina [Polish], CAS-119-64-2, 1,2,3,4-Tetrahydronaphthalene, reagent grade, >=97%, 1,2,3,4-tetrahydronaphthalin, Tetralin solvent, EINECS 270-178-4, TETRAMP, bmse000530, NCIOpen2_000650, 1,3,4-Tetrahydronaphthalene, delta(5,7,9)-Naphthantriene, 1,2,3,4-tetrahydronapthalene, 5,6,7,8-tetrahydronaphthalene, CHEMBL1575635, Naphthalene 1,3,4-tetrahydride, WLN: L66 & TJ, delta(sup 5,7,9)Naphthantriene, Naphthalene 1,2,3,4tetrahydride, Naphthalene, 1,2,3,4tetrahydro, .delta.(sup 5,9)-Naphthantriene, NSC77451, Tox21_201793, Tox21_303325, STL264224, .delta.(sup 5,7,9)-Naphthantriene, AKOS000121383, NCGC00091744-01, NCGC00091744-02, NCGC00256948-01, NCGC00259342-01, DB-300892, NS00008482, T0107, T0713, EN300-21134, 1,2,3,4-Tetrahydronaphthalene, anhydrous, 99%, Q420416, 1,2,3,4-Tetrahydronaphthalene, analytical standard, W-108503, 1,2,3,4-Tetrahydronaphthalene, ReagentPlus(R), 99%, F1908-0164, 1,2,3,4-Tetrahydronaphthalene, Vetec(TM) reagent grade, 98%

Tetralin is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
Tetralin is used in formulation or re-packing, at industrial sites and in manufacturing.

Tetralin is a hydrocarbon having the chemical formula C10H12.
Tetralin is similar to the naphthalene chemical structure except that one ring is saturated.

Tetralin can be synthesized in a Bergman cyclization.
In a classic named reaction called the Darzens tetralin synthesis derivatives can be prepared by intramolecular ring-closing reaction of an 1-aryl-4-pentene with concentrated sulfuric acid, or simply through the hydrogenation of naphthalene in the presence of a platinum catalyst.

Tetralin (1,2,3,4-tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12.
Tetralin is similar to the naphthalene chemical structure except that one ring is saturated.

Tetralin is used as a solvent.
Tetralin is also used for the laboratory synthesis of dry HBr gas.

Tetralins (tetrahydronaphthalenes) are found in many bioactive molecules and the potent biological properties of compounds possessing a tetralin and an oxindole hybrid core are easy to imagine.
However, to our surprise, very few synthetic methods have been reported for tetralin-fused spirooxindoles, especially for a spirooxindole unit at the 2-position of the tetralin core.

Physical Description of Tetralin:
Tetrahydronaphthalene appears as a light colored liquid.
Tetralin may be irritating to skin, eyes and mucous membranes.

Tetralin is a potent antagonist of bacterial fatty acid synthase, which is the key enzyme in the biosynthesis of fatty acids.
Tetralin has been shown to be effective against wild-type strains and mutant strains of Escherichia coli, Salmonella typhimurium, and Staphylococcus aureus.

Tetralin has also been shown to be an antihypertensive compound with a kinetic mechanism that is not yet understood.
The chemical reactions involved in the synthesis of tetralin are most likely due to Tetralin chiral nature.

Physical State: Liquid
Storage: Store at room temperature
Melting Point: -35.8 °C
Boiling Point: 309 °C

Appearance: colorless liquid
Density: 0.970 g/cm3
Melting point: −35.8 °C
Boiling point: 206 to 208 °C

Solubility in water: Insoluble
Viscosity: 2.02 cP at 25 °C
Flash point: 77 °C
Autoignition temperature: 385 °C

Molecular Weight: 132.20
XLogP3: 3.5
Exact Mass: 132.093900383
Monoisotopic Mass: 132.093900383

Topological Polar Surface Area: 0 Å²
Heavy Atom Count: 10
Complexity: 92.6
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Tetralin can also be synthesized by asymmetric synthesis using a surface methodology.
Tetralin has been shown to have no carcinogenic effects in rodent studies.

Tetralin and benzodioxans:
Tetralin (TET), 1,4-benzodioxan (14BZD), and 1,3-benzodioxan (13BZN) are all analogous to the cyclohexene family of molecules and hence have twisted structures with high barriers to planarity.
Because of their low vapor pressures, they have not been studied by far-infrared spectroscopy, but their S0 vibrational data have been obtained using SVLF spectra of the jet-cooled molecules and high-temperature vapor-phase Raman spectra.

Uses of Tetralin:
Tetralin is used as degreasing agent.
Solvent for naphthalene, fats, resins, oils, waxes, used instead of turpentine in lacquers, shoe polishes, floor waxes.

The simultaneous cracking of butylbenzene principally produced benzene.
The reaction rate in the ring-opening of tetralin was considerably high on strong Brønsted acid sites in the 12-ring of the *BEA zeolite.
The amount of Brønsted acid sites on the *BEA zeolite increased the tetralin conversion but did not affect the selectivity to the products.

In tetralin conversion, MOR and FAU zeolites formed more methylindane and naphthalene as by-products, respectively.
Methylindane was produced on weak Brønsted acid sites through ring-contraction of tetralin, and naphthalene was formed on Lewis acid sites through dehydrogenation.
The influences of the reaction conditions on the catalytic activity in tetralin conversion were also investigated.

The contact time increased the conversion, but hardly affected the selectivities to the products.
The total pressure also improved the catalytic activity.

The pressurized hydrogen decreased the selectivity for methylindane, while Tetralin increased for benzene and Tetralin derivatives.
At 573 K, the selectivities to benzene and Tetralin derivatives were high, but the reaction temperature increased the selectivity to the by-products.

Tetralin is used as a hydrogen-donor solvent, for example in coal liquifaction.
Tetralin functions as a source of H2, which is transferred to the coal.

The partially hydrogenated coal is more soluble.
Tetralin has been used in sodium-cooled fast reactors as a secondary coolant to keep sodium seals around pump impellers solidified.
However Tetralin use has been superseded by NaK.

Tetralin is also used for the laboratory synthesis of HBr:
C10H12 + 4 Br2 → C10H8Br4 + 4 HBr

The facility of this reaction is in part a consequence of the moderated strength of the benzylic C-H bonds.

Uses at industrial sites of Tetralin:
Tetralin is used in the following products: coating products, leather treatment products, polymers and heat transfer fluids.
Tetralin has an industrial use resulting in manufacture of another substance (use of intermediates).

Tetralin is used for the manufacture of: chemicals, textile, leather or fur, rubber products and .
Release to the environment of Tetralin can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and of substances in closed systems with minimal release.

Formulation or re-packing of Tetralin:
Tetralin has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of Tetralin can occur from industrial use: formulation of mixtures.

Properties of Tetralin:
Tetralin is Liquid.
Odor resembling that of a mixture of benzene and menthol.
Volatile with steam.

Flash point, open cup 171°F (77°C), closed cup 180°F (82°C).
Insol in water.

Miscible with ethanol, butanol, acetone, benzene, ether, chloroform, petr ether, Decalin.
Soluble in methanol: 50.6% w/w.

Prolonged, intimate contact with air may cause the formn of tetralin peroxide which may cause explosion of tetralin distn residues.
Peroxide formn is prevented by the addn of an antioxidant, such as hydroquinone.
LD50 orally in rats: 2.86 g/kg (Smyth).
Melting point: mp -31.0°

Manufacture of Tetralin:
Release to the environment of Tetralin can occur from industrial use: manufacturing of Tetralin.

Production of Tetralin:
Tetralin is produced by the catalytic hydrogenation of naphthalene.
Although nickel catalysts are traditionally employed, many variations have been evaluated.

Over-hydrogenation converts tetralin into decahydronaphthalene (decalin).
Tetralin is rarely encountered is dihydronaphthalene (dialin).

Laboratory methods of Tetralin:
In a classic named reaction called the Darzens tetralin synthesis, named for Auguste Georges Darzens (1926), derivatives can be prepared by intramolecular electrophilic aromatic substitution reaction of a 1-aryl-4-pentene using concentrated sulfuric acid.

Safety of Tetralin:
LD50 (rats, oral) is 2.68 g/kg.
Tetralin induces methemoglobinemia.