7228-47-9

Usage

Uses

Used in Chemical Synthesis:
2-Naphthaleneethanol is used as a reagent in the chemical-enzymic preparation and resolution of β-naphthyl alcohols. Its unique chemical structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of different compounds.
Used in Pharmaceutical Industry:
As a cinacalcet impurity, 2-Naphthaleneethanol plays a role in the pharmaceutical industry. Cinacalcet is a drug used to treat secondary hyperparathyroidism, and the presence of 2-Naphthaleneethanol can affect the drug's efficacy and safety. Therefore, its identification and control are essential in the manufacturing process of cinacalcet.
Used in Complex Formation:
2-Naphthaleneethanol is used as a component in the formation of complexes and multimers with methyl lactate. These complexes and multimers have potential applications in various fields, including materials science and chemical research.
Used in Sulfated Product Synthesis:
2-Naphthaleneethanol is used as a reactant in the synthesis of sulfated products when combined with sulfur trioxide-dimethylformamide complex and pyridine. These sulfated products may have applications in various industries, such as pharmaceuticals, agrochemicals, and other specialty chemical markets.

InChI:InChI=1/C17H26N5O3P/c1-5-8-14(26(23,24-6-2)25-7-3)9-13(4)10-22-12-21-15-16(18)19-11-20-17(15)22/h11-12H,5-8,10H2,1-4H3,(H2,18,19,20)

Upstream product

• 93-08-3 methyl 2-naphthyl ketone 
• 58464-06-5 2-(1-chloroethyl)naphthalene 
• 827-54-3 2-naphthylethylene 
• 85880-67-7 1-(2-naphthyl)ethyl acetate 
• 88773-87-9 2-(1-napthalenylethoxy)-tetrahydropyran 
• 4541-70-2 2-naphthyllithium 
• 123-38-6 propionaldehyde 
• 917-64-6 methyl magnesium iodide 
• 66-99-9 β-naphthaldehyde 
• 109-72-8 n-butyllithium 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 18987-26-3 trimethyltelluronium iodide 
• 52193-85-8 (R)-1-(2-Naphthyl)ethanol 
• 74-88-4 methyl iodide 

Downstream Products

• 88766-18-1 (+/-)-phthalic acid mono-[1-(naphthyl-⁽²⁾)-ethyl ester] 
• 574-42-5 benzhydryl ether 
• 136908-27-5 2,2'-(1,1'-oxybis(ethane-1,1-diyl))dinaphthalene 
• 136908-16-2 2-(1-Benzhydryloxy-ethyl)-naphthalene 
• 27544-18-9 (S)-1-(2-Naphthyl)ethanol 
• 52193-85-8 (R)-1-(2-Naphthyl)ethanol 
• 93-08-3 methyl 2-naphthyl ketone 
• 85880-67-7 1-(2-naphthyl)ethyl acetate 
• 52428-02-1 2-(1'-bromoethyl)naphthalene 
• 32860-25-6 (R)-1-(2-naphtyl)ethyl acetate 
• 941-98-0 1'-naphthacetophenone 

Relevant academic research and scientific papers

Controlled reduction of aromaticity of alkylated polyaromatic compounds by selective oxidation using H2WO4, H3PO4and H2O2: a route for upgrading heavy oil fractions

Heavy crude oil fractions which form the residues from fractional distillation are a significant proportion of current hydrocarbon reserves. However, processing residues for use as chemicals or fuels is hampered by the high polyaromatic content of this material. Selective reduction of aromaticity by targeted ring opening and the preservation of alkylated chain side groups are key requirements for the upgrading of alkylated polynuclear aromatic hydrocarbons (PAHs) to more easily processed and higher value molecules. In this study, a H2WO4catalyst combined with H3PO4and H2O2oxidant is applied to the selective oxidation of PAHs containing different lengths of substituent alkylated chain, and different numbers of rings in the fused aromatic core. For a model substrate of 2-ethylnaphthalene, using traditional organic solvents, aliphatic carbon was oxidized more readily compared to aromatic carbon. However, it was found that the oxidation to desired products can be specifically controlled as the selectivity is directed by the choice of solvent, with reactions carried out in acetonitrile giving oxidation only in the aromatic region of the molecule. With larger polyaromatic molecules, a biphasic solvent system is used with Aliquat 336 as a phase transfer agent. Even for this more complex reaction system high conversion to the corresponding alkylated ring opened compounds was obtained.

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones

A novel silylene supported iron hydride [Si, C]FeH (PMe3)3 (1) was synthesized by C (sp3)-H bond activation with zero-valent iron complex Fe (PMe3)4. Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp3)?H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.

Pincerlike molybdenum complex and preparation method thereof, catalytic composition and application thereof, and alcohol preparation method

The invention discloses a clamp-type molybdenum complex, a preparation method, a corresponding catalyst composition and application. The method comprises the steps: obtaining 9 molybdenum complexes with different structures through coordination reaction of 2-(substituent ethyl)-(5, 6, 7, 8-tetrahydroquinolyl) amine and a corresponding carbonyl molybdenum metal precursor; and catalyzing a ketone compound transfer hydrogenation reaction through a molybdenum complex to generate 40 alcohol compounds. The preparation method of the molybdenum complex is simple, high in yield and good in stability. For a transfer hydrogenation reaction of ketone, the molybdenum-based catalytic system has high catalytic activity and small molybdenum loading capacity, is used for production of aromatic and aliphatic alcohols, and has the advantages of simple method, small environmental pollution and high yield.

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.

MATERIALS COMPRISING CARBON-EMBEDDED COBALT NANOPARTICLES, PROCESSES FOR THEIR MANUFACTURE, AND USE AS HETEROGENEOUS CATALYSTS

The present invention relates to catalytically active material, comprising grains of non-graphitizing carbon with cobalt nanoparticles dispersed therein, wherein dP, the average diameter of cobalt nanoparticles in the non-graphitizing carbon grains, is in the range of 1 nm to 20 nm, D, the average distance between cobalt nanoparticles in the non-graphitizing carbon grains, is in the range of 2 nm to 150 nm, and ω, the combined total mass fraction of metal in the non-graphitizing carbon grains, is in the range of 30 wt% to 70 wt% of the total mass of the non-graphitizing carbon grains, and wherein dP, D and ω conform to the following relation: 4.5 dP / ω > D ≥ 0.25 dP / ω. The present invention, further, relates to a process for the manufacture of material according to the invention, as well as its use as a catalyst.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol

We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.

Reduction of carbonyl compounds via hydrosilylation catalyzed by well-defined PNP-Mn(I) hydride complexes

Reduction reactions of unsaturated compounds are fundamental transformations in synthetic chemistry. In this context, the reduction of polarized double bonds such as carbonyl or C=C motifs can be achieved by hydrogenation reactions. We describe here a highly chemoselective Mn(I)-based PNP pincer catalyst for the hydrosilylation of aldehydes and ketones employing polymethylhydrosiloxane (PMHS) as inexpensive hydrogen donor. Graphic abstract: [Figure not available: see fulltext.]