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1,2,3,4-Tetrahydronaphthalene

Base Information Edit
  • Chemical Name:1,2,3,4-Tetrahydronaphthalene
  • CAS No.:119-64-2
  • Molecular Formula:C10H12
  • Molecular Weight:132.205
  • Hs Code.:2902 90 00
  • European Community (EC) Number:204-340-2,270-178-4
  • ICSC Number:1527
  • NSC Number:77451
  • UN Number:1993
  • UNII:FT6XMI58YQ
  • DSSTox Substance ID:DTXSID1026118
  • Nikkaji Number:J2.002H
  • Wikipedia:Tetralin
  • Wikidata:Q420416
  • Metabolomics Workbench ID:55060
  • ChEMBL ID:CHEMBL1575635
  • Mol file:119-64-2.mol
1,2,3,4-Tetrahydronaphthalene

Synonyms:1,2,3,4-tetrahydronaphthalene;tetralin

Suppliers and Price of 1,2,3,4-Tetrahydronaphthalene
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Tetrahydronaphthalene
  • 1g
  • $ 45.00
  • TCI Chemical
  • 1,2,3,4-Tetrahydronaphthalene >97.0%(GC)
  • 500mL
  • $ 29.00
  • TCI Chemical
  • 1,2,3,4-Tetrahydronaphthalene >97.0%(GC)
  • 25mL
  • $ 23.00
  • TCI Chemical
  • 1,2,3,4-Tetrahydronaphthalene [for Spectrophotometry] >98.0%(GC)
  • 250mL
  • $ 68.00
  • Sigma-Aldrich
  • 1,2,3,4-Tetrahydronaphthalene ReagentPlus , 99%
  • 100ml
  • $ 61.30
  • Sigma-Aldrich
  • 1,2,3,4-Tetrahydronaphthalene analytical standard
  • 5 mL
  • $ 51.70
  • Sigma-Aldrich
  • 1,2,3,4-Tetrahydronaphthalene analytical standard
  • 5ml-f
  • $ 50.10
  • Sigma-Aldrich
  • 1,2,3,4-Tetrahydronaphthalene reagent grade, ≥97%
  • 18 L
  • $ 866.00
  • Sigma-Aldrich
  • 1,2,3,4-Tetrahydronaphthalene reagent grade, ≥97%
  • 18l-cs
  • $ 836.00
  • Sigma-Aldrich
  • 1,2,3,4-Tetrahydronaphthalene ReagentPlus , 99%
  • 4l
  • $ 314.00
Total 135 raw suppliers
Chemical Property of 1,2,3,4-Tetrahydronaphthalene Edit
Chemical Property:
  • Appearance/Colour:colourless liquid with a mouldy smell 
  • Vapor Pressure:0.18 mm Hg ( 20 °C) 
  • Melting Point:-35 °C(lit.) 
  • Refractive Index:1.5410 - 1.5411 
  • Boiling Point:210.29 °C at 760 mmHg 
  • Flash Point:77.222 °C 
  • PSA:0.00000 
  • Density:0.97 g/cm3 
  • LogP:2.56540 
  • Storage Temp.:Store below +30°C. 
  • Sensitive.:Air Sensitive 
  • Solubility.:0.045g/l 
  • Water Solubility.:INSOLUBLE 
  • XLogP3:3.5
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:0
  • Rotatable Bond Count:0
  • Exact Mass:132.093900383
  • Heavy Atom Count:10
  • Complexity:92.6
  • Transport DOT Label:Combustible Liquid
Purity/Quality:

99% *data from raw suppliers

Tetrahydronaphthalene *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi, Corrosive
  • Hazard Codes:Xi,N,Xn 
  • Statements: 19-36/38-51/53-65-40 
  • Safety Statements: 26-28-61-28A-62-36/37 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Naphthalenes
  • Canonical SMILES:C1CCC2=CC=CC=C2C1
  • Inhalation Risk:A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
  • Effects of Short Term Exposure:The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.
  • Effects of Long Term Exposure:Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the kidneys.
  • General Description 1,2,3,4-Tetrahydronaphthalene (Tetralin) is a hydrogenated derivative of naphthalene, commonly used as a solvent and hydrogen donor in organic reactions. It participates in transfer hydrogenation processes, such as the selective hydrogenation of polycyclic aromatic hydrocarbons (e.g., anthracene and naphthacene) when catalyzed by molten antimony trichloride, forming dihydro derivatives without complete dehydrogenation to naphthalene. Additionally, Tetralin acts as a hydrogen donor in thermal decomposition reactions, where it facilitates reverse radical disproportionation in certain solvents, leading to varied product distributions. Its utility extends to synthetic applications, including Friedel-Crafts cyclizations, where it contributes to the formation of enantiopure tetrahydronaphthalene derivatives.
Technology Process of 1,2,3,4-Tetrahydronaphthalene

There total 366 articles about 1,2,3,4-Tetrahydronaphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With hydrogen; lithium aluminium tetrahydride; titanium(III) chloride; In hexane; at 200 ℃; for 15h; under 67505.4 Torr; Yields of byproduct given;
Guidance literature:
With sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; ammonia; In water; m-xylene; at 150 ℃; for 24h; Inert atmosphere; Sealed tube;
DOI:10.1021/acscatal.8b02214
Refernces Edit

tert-Butyl Hydroperoxide-Pyridinium Dichromate: A Convenient Reagent System for Allylic and Benzylic Oxidations

10.1021/jo00231a046

The research focuses on the development of a more efficient and convenient method for allylic and benzylic oxidations using a reagent system comprised of tert-butyl hydroperoxide and pyridinium dichromate. The purpose of this study was to address the drawbacks of traditional chromium(VI)-based oxidation methods, such as the use of large excess reagents, large volumes of solvents, and long reaction times. The researchers found that the combination of these two reagents in a 1:1 molar ratio effectively facilitated the oxidation process under mild conditions, yielding high conversion rates and product yields. The chemicals used in the process included tert-butyl hydroperoxide, pyridinium dichromate, and various substrates such as cholesteryl acetate, dicyclopentadiene, citronellol acetate, 1-phenylcyclohexene, α-pinene, A3-carene, cycloheptene, limonene, fluorene, diphenylmethane, and tetralin, among others. The conclusions of the research highlighted the utility and simplicity of the tert-butyl hydroperoxide-pyridinium dichromate method, suggesting its potential for wide application in organic synthesis.

Molten Salt Catalyzed Transfer Hydrogenation of Polycyclic Aromatic Hydrocarbons. Selective Hydrogenation of Anthracene and Naphthacene by Tetralin in Molten Antimony Trichloride

10.1021/jo00343a001

The research focuses on the molten salt catalyzed transfer hydrogenation of polycyclic aromatic hydrocarbons, specifically the selective hydrogenation of anthracene and naphthacene by tetralin in the presence of molten antimony trichloride (SbCl3) as a catalyst at 80°C. The study aims to understand the redox-initiated ionic mechanism involving the arene radical cation and the 1-tetralyl cation as key intermediates in these transfer hydrogenation reactions. The conclusions drawn from the research indicate that anthracene and naphthacene are selectively hydrogenated to 9,10-dihydroanthracene and 5,12-dihydronaphthacene, respectively, without forming naphthalene, and instead, the dehydrogenated tetralin reacts with itself and unreacted arene to give alkylated products. The chemicals used in this process include anthracene, naphthacene, tetralin, and molten SbCl3, with additional compounds such as phenanthrene, pyrene, and perylene being tested under similar conditions to understand their reactivity patterns.

Thermal decomposition of O-benzyl ketoximes; role of reverse radical disproportionation

10.1039/b313491a

The research examines the thermal decomposition of various O-benzyl ketoxime ethers (R1R2C(NOCH2Ph)) in three hydrogen donor solvents: tetralin, 9,10-dihydrophenanthrene (DHP), and 9,10-dihydroanthracene (DHA). The study aims to understand the dominant homolytic cleavage modes and the effects of substituents and solvents on the dissociation processes. The results show that the yields of products like imines and benzyl alcohol varied with the solvent, indicating significant involvement of reverse radical disproportionation (RRD) in DHP and DHA, where hydrogen atoms from the solvent transfer to the oxime ethers, followed by β-scission of the resultant radicals. In tetralin, an additional product, benzaldehyde, was observed, suggesting an alternative decomposition mode involving benzylic hydrogen abstraction. The study concludes that the RRD process plays a crucial role in the thermal decomposition of these oxime ethers in certain solvents, and the rates of decomposition and product yields are influenced by both the nature of the substituents and the solvent used.

Acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of α-hydroxy-α-alkenylsilanes

10.1039/c9cc03509e

The research focuses on the acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes, which are compounds containing a benzene ring and a silyl group. The purpose of this study is to synthesize enantiopure organic molecules, a significant challenge in organic synthesis, by leveraging the chirality transfer from a chiral allyl alcohol to a tetrahydronaphthalene product. The researchers used trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a Lewis acid catalyst and found that it effectively promoted the cyclization reaction, yielding vinylsilane-tethered tetrahydronaphthalenes with high optical purity (up to 98% ee).

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