771-29-9

Usage

Uses

Used in Chemical Synthesis:
1,2,3,4-tetrahydro-1-naphthyl hydroperoxide is used as an intermediate in the synthesis of various organic compounds. Its reactivity and stability make it a valuable precursor for the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Oxidation Reactions:
1,2,3,4-tetrahydro-1-naphthyl hydroperoxide is used as an oxidizing agent in various chemical processes. Its ability to transfer oxygen atoms to other molecules makes it useful in the oxidation of organic substrates, leading to the formation of new functional groups and products.
Used in Hydroxylation Reactions:
Chen and Lin used 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide as an intermediate in the hydroxylation of tetralin to tetralol in rat liver homogenate. This application highlights its potential use in biological systems and the study of metabolic pathways.
Used in Catalyst Preparation:
1,2,3,4-tetrahydro-1-naphthyl hydroperoxide can be used in the preparation of catalysts for various industrial processes. Its ability to form metal complexes with transition metals, such as cobalt, manganese, and cerium, makes it a promising candidate for the development of new catalytic systems.

Reactivity Profile

Most alkyl monohydroperoxides are liquid, the explosivity of the lower members (e.g., methyl hydroperoxide, or possibly due to traces of the dialkyl peroxides) decreasing with increasing chain length and branching [Bretherick 2nd ed. 1979 p. 10]. 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide explodes on superheating the liquid [Hock et al. Ber. 1933. pp. 66, 61]. It's interaction with strong reducing agents, like lithium tetrahydroaluminate, is vigorously exothermic.

Purification Methods

Crystallise the tetralin hydroperoxide from hexane, toluene at -30o (m 54.0-54.5o). The oxygen content should be ~9.70%. [Knight & Swern Org Synth Coll Vol 1V 895 1963.]

InChI:InChI=1/C10H12.H2O2/c1-2-6-10-8-4-3-7-9(10)5-1;1-2/h1-2,5-6H,3-4,7-8H2;1-2H

Upstream product

• 119-64-2 tetralin 
• 2653-73-8 azo-bis-α-tetralin 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 

Downstream Products

• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 35387-19-0 2-hydroxybenzenebutanoic acid 
• 55089-05-9 4-(o-hydroxyphenyl)butanal 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1923-89-3 5,6-epoxy-5,6-dihydro-β,β-carotene 
• 108-95-2 phenol 
• 28509-36-6 β-(α-Tetralylperoxy)ethansulfonsaeurephenylester 
• 2845-98-9 Triphenyl-bis-<1.2.3.4-tetrahydro-naphthyl-(1)-peroxy>-arsen 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 447-53-0 1,2-Dihydronaphthalene 
• 22009-40-1 7-amino-1-tetralone 
• 40353-34-2 7-nitro-3,4-dihydro-2H-naphthalen-1-one 
• 752-24-9 3,4,3',4'-tetradehydro-β,β-carotene 
• 13761-10-9 retro-bisdehydrocarotene 

Relevant academic research and scientific papers

Benzylic Hydroperoxidation via Visible-Light-Induced Csp3-H Activation

A highly efficient benzylic hydroperoxidation has been realized through a visible-light-induced Csp3-H activation. We believe that this reaction undergoes a direct HAT mechanism catalyzed by eosin Y. This approach features the use of a metal-free catalyst (eosin Y), an energy-economical light source (blue LED), and a sustainable oxidant (molecular oxygen). Primary, secondary, and tertiary hydroperoxides as well as silyl, benzyl, and acyl peroxides were successfully prepared with good yields and excellent functional group compatibility.

Fabrication of CuCr2O4 spinel nanoparticles: A potential catalyst for the selective oxidation of cycloalkanes via activation of Csp3-H bond

We report here preparation of CuCr2O4 spinel nanoparticle catalyst, mediated by cationic surfactant CTAB in hydrothermal route. XRD revealed the formation of CuCr2O4 spinel phase and TEM showed the particle size of 30-60 nm. The catalyst was speculated to be highly active for selective oxidation of cyclohexane to cyclohexanone with H2O2. A cyclohexane conversion of 70% with 85% cyclohexanone selectivity was achieved over this catalyst at 50 °C temperature. Moreover, the catalyst did not show any significant activity loss even after 8 reuses and proved its efficacy in the oxidation of other cycloalkanes also.

Competition H(D) kinetic isotope effects in the autoxidation of hydrocarbons

Hydrogen atom transfer is central to many important radical chain sequences. We report here a method for determination of both the primary and secondary isotope effects for symmetrical substrates by the use of NMR. Intramolecular competition reactions were carried out on substrates having an increasing number of deuterium atoms at symmetry-related sites. Products that arise from peroxyl radical abstraction at each position of the various substrates reflect the competition rates for H(D) abstraction. The primary KIE for autoxidation of tetralin was determined to be 15.9 ± 1.4, a value that exceeds the maximum predicted by differences in H(D) zero-point energies (～7) and strongly suggests that H atom abstraction by the peroxyl radical occurs with substantial quantum mechanical tunneling.

Selective aerobic oxidation of activated alkanes with MOFs and their use for epoxidation of olefins with oxygen in a tandem reaction

MOFs with Cu2+ centers linked to four nitrogen atoms from azaheterocyclic compounds, i.e., pyrimidine [Cu(2-pymo)2] and imidazole [Cu(im)2], are active catalysts for aerobic oxidation of activated alkanes, such as tetralin, cumene and ethylbenzene. Differences in activity among the two MOFs appear to be related to differences in their ability to decompose the hydroperoxide and to coordinate to the resulting radical OH species. Copper ions in [Cu(im)2] can coordinate by expanding their coordination sphere from 4 to 5 in a reversible way, while in the case of [Cu(2-pymo)2] it results in a displacement of one of the pyrimidine ligands. The MOFs can be used in combination with a silylated Ti-MCM-41 to catalyze the epoxidation of olefins with oxygen by means of a tandem reaction in which the MOF produces cumene hydroperoxide, which is used by Ti-MCM-41 to epoxidize the olefin. The Royal Society of Chemistry 2013.

Superhydrophobic materials as efficient catalysts for hydrocarbon selective oxidation

A new type of superhydrophobic material, FP-Co-SiO2 was prepared with organic groups immobilized on the surface of the SiO2-based nanocomposite. This material showed much higher catalytic activity for selective oxidation of hydrocarbons than an equivalent hydrophilic catalyst.

Highly selective oxidation of tetralin to 1-tetralone over mesoporous CrMCM-41 molecular sieve catalyst using supercritical carbon dioxide

Selective oxidation of tetralin by molecular oxygen over mesoporous CrMCM-41 molecular sieve catalyst using supercritical carbon dioxide (scCO 2) solvent has been investigated. CrMCM-41 catalyst gave high selectivity (96.2%) and good yield (63.4%) of 1-tetralone. The presence of scCO2 medium improves 1-tetralone selectivity and suppresses leaching of chromium from the CrMCM-41. The activity over recycled CrMCM-41 remains nearly the same under the present experimental conditions. The effect of the reaction parameters on CrMCM-41 was also studied in detail along with comparison of its catalytic activities with other mesoporous catalysts, viz. MnMCM-41, CoMCM-41, microporous CrAPO-5, CoMFI, and macroporous Cr/SiO2 catalyst, respectively. In addition this catalytic system was also applied for the oxidation of other benzylic compounds such as indane, fluorene, acenaphthene and diphenylmethane. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.

Metal organic frameworks (MOFs) as catalysts: A combination of Cu2+ and Co2+ MOFs as an efficient catalyst for tetralin oxidation

Two metal-organic frameworks, [Cu(2-pymo)2] and [Co(PhIM)2] (2-pymo = 2-hydroxypyrimidinolate; PhIM = phenylimidazolate), containing respectively Cu2+ and Co2+ ions and anionic diazaheterocyclic ligands (pyrimidinolate and phenylimidazolate) as organic linkers, have been successfully used for the aerobic oxidation of tetralin, yielding α-tetralone (T{double bond, long}O) as the main product. Both materials are stable and recyclable under the reaction conditions. Kinetic studies revealed significant differences between the two MOFs, as a consequence of the different catalytic behavior of their central metal ions. [Cu(2-pymo)2] is highly active for the activation of tetralin to produce tetralinhydroperoxide (T{single bond}OOH), and less efficient in reacting the peroxide. Meanwhile, the use of the cobalt catalyst involves a long induction period for the reaction. However, once T{single bond}OOH is formed, Co2+ rapidly and efficiently transforms this into T{double bond, long}O, with high tetralone-to-tetralol ratio (T{double bond, long}O/T{single bond}OH of ca. 7). The combination of both materials has revealed as a convenient strategy for preparing a highly efficient, selective and reusable catalyst for the liquid phase aerobic oxidation of tetralin.

Synthesis of aromatic aldehydes by aerobic oxidation of hydroaromatic compounds and diarylalkanes using N-hydroxyphthalimide (NHPI) as a key catalyst

Aerobic oxidation of hydroaromatic compounds and diarylalkanes by N-hydroxyphthalimide (NHPI) under mild conditions afforded the corresponding hydroperoxides in high selectivity. Treatment of the resulting hydroperoxides with sulfuric acid followed by neutralization by a base resulted in phenol and aromatic aldehydes in high selectivity. This method provides a convenient synthetic route to aldehydes involving an aromatic moiety.

Solvent-free, heterogeneous photooxygenation of hydrocarbons by Hyflon membranes embedding a fluorous-tagged decatungstate

Hybrid fluoropolymeric membranes with 25% loading of the fluorous-tagged (RfN)4W10O32 effect the solvent-free photooxygenation of benzylic C-H bonds with up to 6100 TONs in 4 hours. The Royal Society of Chemistry 2006.

Kinetic modelling and inverse treatment of the radical mechanism of the liquid-phase autoxidation of 1,2,3,4-tetrahydronaphthalene

A kinetic model to account for the overall radical mechanism of the self-initiated liquid-phase autoxidation of 1,2,3,4-tetrahydronaphthalene (tetralin: RH2) without solvent and without catalyst at 60°C under normal pressure is presented. The model was constructed following a heuristic approach and it consists of 16 elementary steps and a species space including 6 radical and 7 nonradical compounds. Applying inverse computations, the model can be assigned to experimentally observed data within very good agreement where most of the computed values for the kinetic parameters are found to be close to literature values. The respective experimental data is characterized by an autocatalytic time-evolution of tetralin hydroperoxide (HROOH) and of α-tetralone (RO) where in the first stage of autoxidation a remarkable very slow rate of the RO formation in respect to that of the HROOH formation can be observed. This effect is explicitly expressed by the transformation process of tetralyloxy radicals (HRO·) into α-tetralol radicals (·ROH) which react with oxygen yielding RO. The transformation is suggested to be catalyzed by α-tetralol (HROH) which accumulates autocatalytically during the radical chain process. Hence, the nonlinear formation of HROH leads to a switching in the transformation of HRO· into ·ROH radicals which causes a growing rate of RO evolution. The autocatalytic nature of the overall process is explained by degenerate branching of one molecule of HROOH yielding radical species finally resulting into 2 tetralyl radicals (RH·). This process leads to a growing number of chain propagating reaction sequences involving RH· and tetralylperoxy radicals (HROO·) in which RH2 and O2 are consumed and HROOH is formed. Based on the fitting of experimental data the suggested general dynamic structure of the model is validated by computing the reaction fluxes vs. time of several mechanistic key steps. By computer simulations the model is also shown to predict the increase of product accumulation which can be observed experimentally if the autoxidation of RH2 is started after an initial addition of HROH.