614-14-2

Usage

Uses

Used in Chemical Synthesis:
1-Phenyl-1-butanol is used as an intermediate in the synthesis of (E)-1-Phenyl-1-butene (P319495), a compound that is utilized for studying olefin oxidation by cytochrome P-450. This application is significant in understanding the metabolic pathways and enzymatic reactions involving olefins, which are important in various chemical and biological processes.
In the pharmaceutical industry, 1-Phenyl-1-butanol may also be used as a building block for the development of new drugs or drug candidates, given its ability to react with other molecules and form more complex structures. Its versatility in chemical synthesis makes it a valuable component in the creation of a wide range of compounds with potential therapeutic applications.
Additionally, 1-Phenyl-1-butanol could be employed in the fragrance and flavor industry, as its aromatic properties may contribute to the development of unique scents or tastes. 1-PHENYL-1-BUTANOL's potential use in these industries highlights its diverse applications beyond the realm of chemical synthesis and research.

InChI:InChI=1/C10H14O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8,10-11H,2,6H2,1H3

Upstream product

• 123-91-1 1,4-dioxane 
• 91-01-0 1,1-Diphenylmethanol 
• 556-91-2 aluminum tri-tert-butoxide 
• 495-40-9 propiophenone 
• 10557-57-0 propylmagnesium iodide 
• 100-52-7 benzaldehyde 
• 4392-30-7 phenylcyclobutane 
• 3481-02-5 cyclopropyl phenyl ketone 
• 57204-89-4 α-(phenylseleno)butyrophenone 
• 22144-60-1 (R)-1-butylphenylethanol 
• 540-54-5 1-Chloropropane 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 107-92-6 butyric acid 

Downstream Products

• 119-61-9 benzophenone 
• 91-01-0 1,1-Diphenylmethanol 
• 495-40-9 propiophenone 
• 5702-42-1 5-ethyl-4-phenyl-[1,3]dioxane 
• 824-90-8 1-phenylbut-1-ene 
• 27059-40-1 (1-chlorobutyl)benzene 
• 84473-31-4 4-(Bromobutyl)benzene 
• 7476-99-5 1-phenylbutyl butyrate 
• 7476-99-5 (+)(R)-1-butyryloxy-1-phenyl-butane 
• 19031-71-1 (1-fluorobutyl)benzene 
• 121508-86-9 2-<(1-phenylbutoxy)methyl>oxirane 
• 197709-33-4 N-(1-phenylbutoxy)phthalimide 
• 22144-60-1 (R)-1-butylphenylethanol 
• 22135-49-5 (S)-1-phenylbutan-1-ol 

Relevant academic research and scientific papers

Zirconium-catalyzed cyclopropanation of α-olefins mediated by R′CO2R″ and ClnAlEt3-n

A Cp2ZrCl2-catalyzed one-pot cyclopropanation method has been developed to afford alkoxycyclopropanes and cyclopropanols from α-olefins involving esters of carboxylic acids and ClnAlEt 3-n.

The Comparative Effect of Particle Size and Support Acidity on Hydrogenation of Aromatic Ketones

A comparative study was reported for both the effects of shape-confined cubic Pd particle size (8, 13, and 21 nm) and surface property of most commonly used supports (SiO2, Al2O3, and silica-alumina) on catalytic performance in the chemoselective hydrogenation of three model bio-oil chemicals (benzaldehyde, acetophenone, and butyrophenone). The results showed that the size of Pd particles could be more associated with the hydrogenation reaction than acidities of the supports. Smaller size of Pd particles, regardless of the type of the support, provided the higher catalytic performance. XPS data showed that the electronic properties of Pd particles were similar, therefore, the possible reasons were the higher fraction of Pd atoms on corner in smaller particles, the lower accessibility of hydrogen atom to reactant on bigger particles, and the more low-coordinated sites in the small-size particles due to the short-range ordering. In addition, Pd/SA catalysts (Br?nsted acid sites on the support) showed the highest conversion and TOF compared to Pd/Al2O3 and Pd/SiO2 catalysts. This might be due to the enhanced the diffusion rates of the chemicals on the surface of the catalysts although they could not induce the ionic effect from the metal surface. Pd/SiO2 catalysts performed better than Pd/Al2O3 catalysts (Lewis acid sites on the support). The flexible SiOH groups on surface made the easy interaction with the metal particles and promote the reaction.

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.

Method for synthesizing secondary alcohol in water phase

The invention discloses a method for synthesizing secondary alcohol in a water phase. The method comprises the following steps: taking ketone as a raw material, selecting water as a solvent, and carrying out catalytic hydrogenation reaction on the ketone in the presence of a water-soluble catalyst to obtain the secondary alcohol, wherein the catalyst is a metal iridium complex [Cp * Ir (2, 2'-bpyO)(OH)][Na]. Water is used as the solvent, so that the use of an organic solvent is avoided, and the method is more environment-friendly; the reaction is carried out at relatively low temperature and normal pressure, and the reaction conditions are mild; alkali is not needed in the reaction, so that generation of byproducts is avoided; and the conversion rate of the raw materials is high, and the yield of the obtained product is high. The method not only has academic research value, but also has a certain industrialization prospect.

Ruthenium-p-cymene Complex Side-Wall Covalently Bonded to Carbon Nanotubes as Efficient Hybrid Transfer Hydrogenation Catalyst

A half-sandwich ruthenium-p-cymene organometallic complex has been immobilized at Single Walled Carbon Nanotubes (SWNT) sidewalls through a stepwise covalent chemistry protocol. The introduction of amino groups by means of diazonium-chemistry protocols leads the grafting at the outer walls of the nanotubes. This hybrid material is active in the transfer hydrogenation of ketones to yield alcohols, using as hydrogen source 2-propanol. SWNT?NH2?Ru presents a broad scope, performing the reaction under aerobic conditions and can be recycled over 9 consecutive reaction runs without losing activity or leaching ruthenium out. Comparison of the activity with related homogeneous catalysts reveals an improved performance due to the covalent bond between the metal and the material, achieving turnover frequencies as high as 192774 h?1.

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.

Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities

Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.

Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds

The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.

Postsynthetic Modification of Half-Sandwich Ruthenium Complexes by Mechanochemical Synthesis

A mild and environmentally friendly method to synthesize half-sandwich ruthenium complexes through the Wittig reaction between an aldehyde-tagged half-sandwich ruthenium complex and phosphorus ylide mechanochemically is reported herein. The mechanochemical synthesis of valuable half-sandwich ruthenium complexes resulted in a fast reaction, good yield with simple workup, and the avoidance of harsh reaction conditions and organic solvents. The synthesized half-sandwich ruthenium complexes exhibited high catalytic activity for transfer hydrogenation of ketones using 2-propanol as the hydrogen source and solvent. Density functional theory was carried out to propose a mechanism for the transfer hydrogenation process. The modeling suggests the importance of the labile p-cymene ligand in modulating the reactivity of the catalyst.