TETRALIN

Tetralin = 1,2,3,4-Tetrahydronaphthalene

CAS Number  : 119-64-2 
EC  Number  : 204-340-2
ECHA InfoCard    : 100.003.946 
PubChem CID    : 8404
ChemSpider    : 8097 
ChEBI           : CHEBI:35008 
Chemical formula : C10H12
Molar mass     : 132.206 g·mol−1
Density             : 0.970 g/cm3
Melting point     : −35.8 °C
Boiling point     : 206 to 208 °C
Viscosity     : 2.02 cP at 25 °C
Appearance     : colorless liquid with an odor similar to naphthalene
Flash point     : 77 °C

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

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). 
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.

Uses of Tetralin
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fast reactors as a secondary coolant to keep sodium seals around pump impellers solidified; however its use has been superseded by NaK.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.

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

Tetralin appears as a light colored liquid. 
May be irritating to skin, eyes and mucous membranes.
Tetralin is an ortho-fused bicyclic hydrocarbon that is 1,2,3,4-tetrahydro derivative of naphthalene. 
Tetralin is an ortho-fused bicyclic hydrocarbon and a member of tetralins. 
Tetralin derives from a hydride of a naphthalene.

Use and Manufacturing of Tetralin
Used in the solvent, paint, varnish, and rubber industries; tetralin is used in shoe polish and floor wax; [HSDB]
SOLVENT FOR CAMPHOR, SULFUR & IODINE; IN PAINT THINNERS; AS PAINT REMOVER WHEN MIXED WITH DECALIN OR WHITE SPIRIT; AS INSECTICIDE FOR CLOTHES MOTH; AS SUBSTITUTE FOR TURPENTINE & PETROL IN GERMANY.
SOLVENT FOR NAPHTHALENE, FATS, RESINS, OILS, WAXES, USED INSTEAD OF TURPENTINE IN LACQUERS, SHOE POLISHES, FLOOR WAXES; DEGREASING AGENT.
IN PLANT PATHOLOGY, TETRALIN HAS BEEN SUCCESSFUL IN TOTAL DESTRUCTION OF CROWN GALL AND OLIVE KNOT NEOPLASMS.
A COMBINATION OF 31% TETRAHYDRONAPHTHALENE AND 0.03% CUPRIC OLEATE (CUPREX) IS PROMOTED AS A PEDICULICIDE AND MITICIDE, BUT ITS TRUE EFFICACY REMAINS TO BE DETERMINED.

Industry Uses of Tetralin
-Intermediates
-Lubricants and lubricant additives

Consumer Uses of Tetralin
-Lubricants and greases

Tetralin (1,2,3,4-Tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12. 
This molecule is similar to the naphthalene molecular structure but where 2 of the double bonds are saturated. 
Tetralins CAS number is 119-64-2.

The compound can be synthesized in a Bergman cyclization. 
In a classic named reaction called the Darzens tetralin synthesis (Auguste George Darzens (1867-1954), 1926) 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 napthalene in the presence of a platinum catalyst.

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.

Specifications of Tetralin
Appearance  : Clear liquid
Color/Hazen (GB/T 605)    : ≤20
1,2,3,4-Tetrahydronaphthalene (GC) : ≥99.0%
Decahydronaphthalene (GC) : ≤1.0%
Naphthalene (GC) : ≤0.5%

1,2,3,4-Tetrahydronaphthalene Usage

1.Tetralin is an important intermediate for the preparation of naphthol, which can be used to synthesize pesticides such as naphthalene amine and dichlorochlor.

2.Testing manganese. Degreasing agent. Intermediate. Solvents for Naphthalene, Oils and Resins.

3.Used as solvent and reagent for chromatographic analysis.

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

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. 
Tetralin (1,2,3,4-tetrahydonaphthalene) is a recalcitrant compound that consists of an aromatic and an alicyclic ring. 
Tetralin is found in crude oils, produced industrially from naphthalene or anthracene, and widely used as an organic solvent. 
Tetralins toxicity is due to the alteration of biological membranes by its hydrophobic character and to the formation of toxic hydroperoxides.

Tetralin can be hydrogenated (mainly to tetralin) to the extent of 75–80% on hydrogenating it at a hydrogen pressure of 20 atm, a temperature of 350–370dgC, and a crude feed of 0.25–1.0 kg/liter · h, on using Al2O3 + CoO + MoO3 catalyst. 
The hydrogenation conversion level of 2-methylnaphthalene is 1.5 times less. 
Tetralin can be hydrogenated to the extent of 90–95% at a pressure of 40 atm on using a tungsten— nickel—sulfide catalyst. 
A significant fraction of the tetralin formed is, however, hydrogenated further to the decalins.

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

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

Tetralin (1,2,3,4-tetrahydronaphthalene) is a widely used organic solvent for fats, resins and waxes. 
Tetralin can also be found in many household products like paints, lacquers and shoe polishes. 
Tetralin absorbed in cells may form toxic hydroperoxides and inhibit bacterial growth in concentrations higher than 100 micromoles/liter. 
Due to its lipophilic nature, tetralin accumulates in cell membranes resulting in structural and functional changes

High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic bromination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene as a major product and several secondary products. 
Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene  gave 1,4-dibromonaphthalene  as the sole product in a high yield. 
Tetralin is efficiently converted to the corresponding methoxy  and cyano  derivatives of naphthalene.

First Aid Measures of Tetralin

Eye Contact:
Check for and remove any contact lenses. 
In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. 
Get medical attention.

Skin Contact:
In case of contact, immediately flush skin with plenty of water. 
Cover the irritated skin with an emollient.
Remove contaminated clothing and shoes. 
Wash clothing before reuse. 
Thoroughly clean shoes before reuse.
Get medical attention.

Serious Skin Contact:
Wash with a disinfectant soap and cover the contaminated skin with an anti-bacterial cream. 
Seek immediate medical attention.

Inhalation:
If inhaled, remove to fresh air. 
If not breathing, give artificial respiration. 
If breathing is difficult, give oxygen. 
Get medical attention.

Ingestion:
Do not induce vomiting. 
Loosen tight clothing such as a collar, tie, belt or waistband. 
If the victim is not breathing, perform mouth-to-mouth resuscitation. 
Seek immediate medical attention.

Substance identity

EC / List no.: 204-340-2
CAS no.: 119-64-2
Mol. formula: C10H12

Hazard classification & labelling of Tetralin
Warning! According to the harmonised classification and labelling (CLP00) approved by the European Union, Tetralin is toxic to aquatic life with long lasting effects, causes serious eye irritation and causes skin irritation.
Additionally, the classification provided by companies to ECHA in REACH registrations identifies that Tetralin may be fatal if swallowed and enters airways and is suspected of causing cancer.

About Tetralin
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.

Consumer Uses of Tetralin
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the routes by which Tetralin is most likely to be released to the environment.

Article service life of Tetralin
ECHA has no public registered data on the routes by which Tetralin is most likely to be released to the environment. 
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers of Tetralin
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. 
ECHA has no public registered data on the types of manufacture using Tetralin. 
ECHA has no public registered data on the routes by which Tetralin is most likely to be released to the environment.

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.

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.

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

Synonyms:
1,2,3,4-Tetrahydronaphthalene
TETRALIN
119-64-2
Benzocyclohexane
Tetrahydronaphthalene
Bacticin
Tetraline
Tetranap
Naphthalene, 1,2,3,4-tetrahydro-
Tetralina
Naphthalene, tetrahydro-
Naphthalene 1,2,3,4-tetrahydride
tetralene
UNII-FT6XMI58YQ
NSC 77451
(C4-C5) Alkyltetrahydronaphthalenes
FT6XMI58YQ
Naphthalene, 1,2,3,4-tetrahydro-, C1-4-alkyl derivs.
CHEBI:35008
1,2,3,4-tetrahydro-naphthalene
MFCD00001733
DSSTox_CID_6118
DSSTox_RID_78023
DSSTox_GSID_26118
68412-24-8
Tetralina [Polish]
Caswell No. 842A
CAS-119-64-2
CCRIS 3564
HSDB 127
delta(sup 5,7,9)-naphthantriene
EINECS 204-340-2
1,2,3,4-Tetrahydronaphthalene, reagent grade, >=97%
EPA Pesticide Chemical Code 055901
AI3-01257
Tetralin solvent
EINECS 270-178-4
bmse000530
EC 204-340-2
NCIOpen2_000650
1,3,4-Tetrahydronaphthalene
1,2,3,4-tetrahydronapthalene
5,6,7,8-tetrahydronaphthalene
CHEMBL1575635
DTXSID1026118
Naphthalene 1,3,4-tetrahydride
WLN: L66 & TJ
1,2,3,4 Tetrahyclronaphthalene
.delta.(5,7,9)-Naphthantriene
.delta.(sup 5,9)-Naphthantriene
Naphthalene-1,2,3,4-tetrahydride
NSC77451
ZINC8437660
Tox21_201793
Tox21_303325
NSC-77451
STL264224
.delta.(sup 5,7,9)-Naphthantriene
AKOS000121383
LS40429
MCULE-8327072794
NCGC00091744-01
NCGC00091744-02
NCGC00256948-01
NCGC00259342-01
I899
FT-0654145
T0107
T0713
1,2,3,4-tetrahydronaphthalene, Tetralin, THN
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%
1,2,3,4-tetrahydronaphthalene
1,2,3,4-tetrahydronaphthalene
1,2,3,4-Tetrahydronaphthalene
1,2,3,4-tetrahidronaftalen (hr)
1,2,3,4-tetrahidronaftalen (sl)
1,2,3,4-tetrahidronaftalenas (lt)
1,2,3,4-tetrahidronaftaleno (es)
1,2,3,4-tetrahidronaftaleno (pt)
1,2,3,4-tetrahidronaftalin (hu)
1,2,3,4-tetrahidronaftalina (ro)
1,2,3,4-tetrahidronaftalīns (lv)
1,2,3,4-tetrahydronaftaleen (nl)
1,2,3,4-tetrahydronaftaleeni (fi)
1,2,3,4-tetrahydronaftalen (cs)
1,2,3,4-tetrahydronaftalen (no)
1,2,3,4-tetrahydronaftalen (pl)
1,2,3,4-tetrahydronaftalen (sv)
1,2,3,4-tetrahydronaftalén (sk)
1,2,3,4-tetrahydronaphtalen (da)
1,2,3,4-Tetrahydronaphthalin (de)
1,2,3,4-Tetrahüdronaftaleen (et)
1,2,3,4-tetraidronaftalene (it)
1,2,3,4-tétrahydronaphtalène (fr)
1,2,3,4-τετραϋδροναφθαλένιο (el)
1,2,3,4-тeтрахидронафталeн (bg)
tetralina (pl)
Naphthalene, 1,2,3,4-tetrahydro-
2,3,4-tetrahydronaphthalene
1,2,3,4-tetrahydronaphtalene
1,2,3,4-Tetrahydronaphthalene
1,2,3,4-tetrahydronaphthalene
1,2,3,4-tetrahydronaphthalene
1,2,3,4-Tetrahydronaphthalin
Tetrahydronaphthalene
tetralinova frakce
tetralín
119-64-2
601-045-00-4
1,2,3,4-Tétrahydronaphtalène [French] [ACD/IUPAC Name]
1,2,3,4-Tetrahydronaphthalen
1,2,3,4-Tetrahydronaphthalene [ACD/IUPAC Name]
1,2,3,4-Tetrahydronaphthalin [German] [ACD/IUPAC Name]
119-64-2 [RN]
1446407 [Beilstein]
204-340-2 [EINECS]
FT6XMI58YQ
MFCD00001733 [MDL number]
Naphthalene, 1,2,3,4-tetrahydro- [ACD/Index Name]
tetrahydronaphthalene
Tetralin [Wiki]
Tetralin(R) solvent
Tetralina [Polish]
Tetraline [Dutch]
Tétraline [French]
四氢化萘 [Chinese]
[119-64-2] [RN]
1,2,3, 4-Tetrahydronaphthalene
1,2,3,4-Tetrahydronaphthalene 10 µg/mL in Methanol
1,2,3,4-tetrahydronaphthalene(tetralin)
1,2,3,4-tetrahydronaphthalene, Tetralin, THN
1,2,3,4-Tetrahydronaphthalene;Tetralin
1,2,3,4-TETRHYDRONAPHTHALENE
204-340-2MFCD00001733
270-178-4 [EINECS]
68412-24-8 [RN]
benzocyclohexane
C095210
EINECS 204-340-2
EINECS 270-178-4
naphthalene 1,2,3,4-tetrahydride
NAPHTHALENE, TETRAHYDRO-
Naphthalene-1,2,3,4-tetrahydride
pWLN: L66 & TJ
teteralin
tetralene
Tetralin(TM) solvent
Tetralin?
Tetralina
Tetralina [Polish]
Tetraline
Tetrana
TETRANAP
THN
UNII:FT6XMI58YQ
UNII-FT6XMI58YQ
WLN: L66 & TJ
δ(5,7,9)-Naphthantriene
δ(sup 5,7,9)-naphthantriene
δ(sup 5,7,9)-Naphthantriene