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 
• 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 
• 27544-18-9 (S)-1-(2-Naphthyl)ethanol 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 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 
• 58464-06-5 2-(1-chloroethyl)naphthalene 

Relevant academic research and scientific papers

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.]

Manganese-Catalyzed Hydrogenation of Ketones under Mild and Base-free Conditions

In this paper, several Mn(I) complexes were applied as catalysts for the homogeneous hydrogenation of ketones. The most active precatalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe) (CO)3(CH2CH2CH3)]. The reaction proceeds at room temperature under base-free conditions with a catalyst loading of 3 mol % and a hydrogen pressure of 10 bar. A temperature-dependent selectivity for the reduction of α,β-unsaturated carbonyls was observed. At room temperature, the carbonyl group was selectively hydrogenated, while the C=C bond stayed intact. At 60 °C, fully saturated systems were obtained. A plausible mechanism based on DFT calculations which involves an inner-sphere hydride transfer is proposed.

Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water

A green, efficient, and high active catalytic system for the hydrogenation of ketones and aldehydes to produce corresponding alcohols under atmospheric-pressure H2 gas and ambient temperature conditions was developed by a water-soluble metal–ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(OH)][Na] in water without addition of a base. The catalyst exhibited high activity for the hydrogenation of ketones and aldehydes. Furthermore, it was worth noting that many readily reducible or labile functional groups in the same molecule, such as cyan, nitro, and ester groups, remained unchanged. Interestingly, the unsaturated aldehydes can be also selectively hydrogenated to give corresponding unsaturated alcohols with remaining C=C bond in good yields. In addition, this reaction could be extended to gram levels and has a large potential of wide application in future industrial.