5391-88-8

Usage

Uses

1. Used in Chemical Synthesis:
1-(4-Bromophenyl)ethanol is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a valuable building block in the synthesis of complex molecules, particularly in the pharmaceutical and chemical industries.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(4-Bromophenyl)ethanol is used as a key component in the development of new drugs. Its chemical properties make it suitable for the synthesis of various medicinal compounds, potentially leading to the discovery of novel therapeutic agents.
3. Used in Chemical Research:
1-(4-Bromophenyl)ethanol is also utilized in chemical research as a model compound to study various reaction mechanisms and to understand the behavior of similar molecules. This helps researchers in developing new synthetic methods and improving existing ones.
4. Used in Material Science:
The unique properties of 1-(4-Bromophenyl)ethanol make it a potential candidate for the development of new materials with specific characteristics. It can be used in the synthesis of advanced materials for various applications, such as electronics, coatings, and adhesives.

InChI:InChI=1/C8H9BrO/c1-6(10)7-2-4-8(9)5-3-7/h2-6,10H,1H3/t6-/m1/s1

Upstream product

• 103966-62-7 4-(α-acetoxyethyl)-1-bromobenzene 
• 17279-31-1 (-)-(S)-N,N-dimethyl-1-phenylethylamine 
• 108-24-7 acetic anhydride 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 247210-85-1 (1-(4-bromophenyl)ethoxy)diphenylsilane 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-05-4 vinyl acetate 
• 75-24-1 trimethylaluminum 
• 1122-91-4 4-bromo-benzaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 1260183-58-1 C₁₁H₁₇BrOSi 
• 99-90-1 para-bromoacetophenone 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 1007587-62-3 (R)-1-(4-trimethylsilylethynylphenyl)ethanol 
• 1007587-61-2 (R)-1-(4-((trimethylsilyl)ethynyl)phenyl)ethan-1-ol 
• 103966-62-7 (R)-1-(4-bromophenyl)ethyl acetate 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 97364-15-3 4-(1-hydroxyethyl)benzoic acid 
• 99-90-1 para-bromoacetophenone 
• 20488-10-2 1-(1-chloroethyl)-4-bromobenzene 
• 159755-11-0 1-bromo-4-(1-bromoethyl)benzene 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 67595-65-7 1-(4'-Bromphenyl)-ethyl-kation 
• 5391-88-8 (S)-1-(4-bromophenyl)ethanol 
• 137408-29-8 (S)-1-(4-bromophenyl)ethyl acetate 
• 159298-92-7 1-(4-bromophenyl)ethyl methanesulfonate 
• 59891-97-3 (rac.)-1-bromo-4-(1-methoxyethyl)benzene 

Relevant academic research and scientific papers

Hydrosilylation of Aldehydes and Ketones Catalyzed by a 2-Iminopyrrolyl Alkyl-Manganese(II) Complex

A well-defined and very active single-component manganese(II) catalyst system for the hydrosilylation of aldehydes and ketones is presented. First, the reaction of 5-(2,4,6-iPr3C6H2)-2-[N-(2,6-iPr2C6H3)formimino]pyrrolyl potassium (KL) and [MnCl2(Py)2] afforded the binuclear 2-iminopyrrolyl manganese(II) pyridine chloride complex [Mn2{κ2N,N′-5-(2,4,6-iPr3C6H2)-NC4H2-2-C(H)═N(2,6-iPr2C6H3)}2(Py)2(μ-Cl)2] 1. Subsequently, the alkylation reaction of complex 1 with LiCH2SiMe3 afforded the respective (trimethylsilyl)methyl-Mn(II) complex [Mn{κ2N,N′-5-(2,4,6-iPr3C6H2)-NC4H2-2-C(H)═N(2,6-iPr2C6H3)}(Py)CH2SiMe3] 2 in a good yield. Complexes 1 and 2 were characterized by elemental analysis, 1H NMR spectroscopy, Evans' method, FTIR spectroscopy, and single-crystal X-ray diffraction. While the crystal structure of complex 1 has been identified as a binuclear entity, in which the Mn(II) centers present pentacoordinate coordination spheres, that of complex 2 corresponds to a monomer with a distorted tetrahedral coordination geometry. Complex 2 proved to be a very active precatalyst for the atom-economic hydrosilylation of several aldehydes and ketones under very mild conditions, with a maximum turnover frequency of 95 min-1, via a silyl-Mn(II) mechanistic route, as asserted by a combination of experimental and theoretical efforts, the respective silanes were cleanly converted to the respective alcoholic products in high yields.

Exploration of highly electron-rich manganese complexes in enantioselective oxidation catalysis; A focus on enantioselective benzylic oxidation

The direct enantioselective hydroxylation of benzylic C-H bonds to form chiral benzylic alcohols represents a challenging transformation. Herein, we report on the exploration of new biologically inspired manganese and iron complexes bearing highly electron-rich aminopyridine ligands containing 4-pyrrolidinopyridine moieties ((S,S)-1, (R,R)-1, 2 and 5) in combination with chiral bis-pyrrolidine and N,N-cyclohexanediamine backbones in enantioselective oxidation catalysis with aqueous H2O2. The current manganese complexes outperform the analogous manganese complexes containing 4-dimethylaminopyridine moieties (3 and 4) in benzylic oxidation reactions in terms of alcohol yield while keeping similar ee values (～60% ee), which is attributed to the higher basicity of the 4-pyrrolidinopyridine group. A detailed investigation of different carboxylic acid additives in enantioselective benzylic oxidation provides new insights into how to rationally enhance enantioselectivities by means of proper tuning of the environment around the catalytic active site, and has resulted in the selection of Boc-l-Tert-leucine as the preferred additive. Using these optimized conditions, manganese complex 2 was shown to be effective in the enantioselective benzylic oxidation of a series of arylalkane substrates with up to 50% alcohol yield and 62% product ee. A final set of experiments also highlights the use of the new 4-pyrrolidinopyridine-based complexes in the asymmetric epoxidation of olefins (up to 98% epoxide yield and >99% ee).

Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes

Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.

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.

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.

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.]

Synthesis of new rhodium(III) complex by benzylic C[sbnd]S bond cleavage of thioether containing NNS donor Schiff base ligand: Investigation of catalytic activity towards transfer hydrogenation of ketones

A new rhodium(III)-triphenylphosphine mixed ligand complex, [Rh(PPh3)(L)Cl2] (1) is synthesized by benzylic C[sbnd]S bond cleavage of L-CH2Ph ligand (where, L-CH2Ph = 2-(benzylthio)-N-(pyridin-2-ylmethylene)aniline). The complex is thoroughly characterized by several spectroscopic techniques. Geometry of the complex is confirmed by single crystal X-ray crystallography. Electronic structure, redox properties, absorption and emission properties of the complex were studied. DFT and TDDFT calculations were carried out to interpret the electronic structure and absorption properties of the complex respectively. The synthesized Rh(III) complex was tested as catalyst towards transfer hydrogenation reaction of ketones in iPrOH and an excellent catalytic conversion was observed under mild conditions.

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.

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.

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.