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 
• 876-27-7 4-chlorophenyl acetate 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 330825-67-7 (S)-1-(4-bromophenyl)-1-(trichlorosilyl)ethane 
• 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 
• 544-97-8 dimethyl zinc(II) 
• 1122-91-4 4-bromo-benzaldehyde 
• 84782-03-6 1-methylheptyl propionate 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 

Downstream Products

• 1007587-62-3 (R)-1-(4-trimethylsilylethynylphenyl)ethanol 
• 1257224-09-1 (S)-1-(4-bromophenyl)ethyl propionate 
• 1007587-61-2 (R)-1-(4-((trimethylsilyl)ethynyl)phenyl)ethan-1-ol 
• 79322-76-2 (R)-4'-(1-hydroxy-ethyl)benzoic methyl ester 
• 24308-78-9 (+)-1-(4'-bromophenyl)bromoethane 
• 25444-33-1 4-Perfluor-heptyl-1-<1-hydroxy-ethyl>-benzol 

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.

Chitosan as a chiral ligand and organocatalyst: Preparation conditions-property-catalytic performance relationships

Chitosan is an abundant and renewable chirality source of natural origin. The effect of the preparation conditions by alkaline hydrolysis of chitin on the properties of chitosan was studied. The materials obtained were used as ligands in the ruthenium-catalysed asymmetric transfer hydrogenation of aromatic prochiral ketones and oxidative kinetic resolution of benzylic alcohols as well as organocatalysts in the Michael addition of isobutyraldehyde to N-substituted maleimides. The degrees of deacetylation of the prepared materials were determined by 1H NMR, FT-IR and UV-vis spectroscopy, the molecular weights by viscosity measurements, their crystallinity by WAXRD, and their morphology by SEM and TEM investigations. The materials were also characterized by Raman spectroscopy. The biopolymers which have molecular weights in a narrow (200-230 kDa) range and appropriate (80-95%) degrees of deacetylation were the most efficient ligands in the enantioselective transfer hydrogenation, whereas in the oxidative kinetic resolution the activity of the complexes and the stereoselectivity increased with the degree of deacetylation. The chirality of the chitosan was sufficient to obtain enantioselection in the Michael addition of isobutyraldehyde to maleimides in the aqueous phase. Interestingly, the biopolymer afforded the opposite enantiomer in excess compared to the monomer, d-glucosamine. In this reaction, good correlation between the degree of deacetylation and the catalytic activity was found. These results are novel steps in the application of this natural, biocompatible and biodegradable polymer in developing environmentally benign methods for the production of optically pure fine chemicals.

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).

Copper-catalyzed asymmetric reductions of aryl/heteroaryl ketones under mild aqueous micellar conditions

Enantioselective syntheses of nonracemic secondary alcohols have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)2·H2O/(R)-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodology serves as a green protocol to access enantio-enriched alcohols under mild conditions (0-22 °C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alcohol products are formed in good to excellent yields with ee values greater than 90%.

One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, withee> 99%.

Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Asymmetric catalytic reactions are among the most convenient and environmentally benign methods to obtain optically pure compounds. The aim of this study was to develop a green system for the asymmetric transfer hydrogenation of ketones, applying chiral Ru catalyst in aqueous media and mechanochemical energy transmission. Using a ball mill we have optimized the milling parameters in the transfer hydrogenation of acetophenone followed by reduction of various substituted derivatives. The scope of the method was extended to carbo- and heterocyclic ketones. The scale-up of the developed system was successful, the optically enriched alcohols could be obtained in high yields. The developed mechanochemical system provides TOFs up to 168 h?1. Our present study is the first in which mechanochemically activated enantioselective transfer hydrogenations were carried out, thus, may be a useful guide for the practical synthesis of optically pure chiral secondary alcohols.

C3 The symmetry contains a chiral ligand H3L of an amide bond. Preparation method and application

The invention discloses C. 3 Chiral ligand H with symmetric amide bond3 L Relates to the technical field of material chemistry and chiral chemistry. The invention further provides the chiral ligand H. 3 L Preparation method and application thereof. The present invention has the advantage that the chiral ligand H of the present invention is a chiral ligand. 3 The L has a higher C. 3 The symmetric and flexible amide group enables coordination of the lanthanide metal ions with high coordination number and high oxygen affinity to be assembled into a novel structure-structure lanthanide metal chiral porous coordination cage. Moreover, the abundant chiral amide groups and amino acid residues on the ligand framework can be directly introduced into the synthesized lanthanide metal chiral porous coordination cage, thereby being beneficial to generating multiple chiral recognition sites and unique chiral microenvironments which mimic the biological enzyme binding pocket and further realize the purpose of high enantioselectivity separation of a series of chiral small molecule compounds.

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

Hetero- A nd Homobimetallic Complexes Bridged by a Bis(NHC) Ligand: Synthesis via Selective Sequential Metalation and Catalytic Applications in Tandem Organic Transformations

A (bis)azolium salt [L1-H2]Br2 (5), synthesized following multistep procedures, was realized to be a suitable platform for accessing the bis(NHC) ligand supported heterobimetallic IrIII-M (M = PdII/AuI) complexes via a sequential metalation strategy for their potential catalytic applications in one-pot tandem organic transformations. First, the reaction of 5 with 0.5 equiv of [Ir(Cp-)Cl2]2 selectively yielded a monometallic IrIII complex 6, which was further metalated using Pd(OAc)2/NaOAc to afford the heterobimetallic IrIII-PdII complex 7. On the other hand, complex 6 was reacted with Ag2O, followed by transmetalation with [Au(SMe2)Cl] in a one-pot manner, to yield the IrIII-AuI complex 8. Further, the related homobimetallic IrIII and PdII complexes 9 and 10, respectively, have also been synthesized directly from [L1-H2]Br2. All the homo/heterobimetallic complexes have been well-characterized by multinuclear NMR spectroscopy, ESI-mass spectrometry, and via single-crystal X-ray diffraction studies of the complexes 7, 8, and 10. The heterobimetallic IrIII-PdII complex 7 has been tested as a catalyst for three one-pot tandem catalytic reactions: (a) Suzuki-Miyaura coupling and transfer hydrogenation of ketones, (b) hydrodefluorination and transfer hydrogenation of ketones, and (c) hydrodehalogenation and transfer hydrogenation of imines. Importantly, the catalytic activity of heterobimetallic complex 7 in the above-mentioned reactions was found to be better than the mixture of their corresponding homobimetallic counterparts 9 and 10, keeping the concentration of the metal centers constant. These observations affirm some sort of cooperativity between the two metal centers (Ir and Pd) connected via a single ligand frame in 7 when catalytic activity is concerned, which thus constitutes a superior catalytic system than that of the cases where two separate metal complexes (hence, the two metal centers are not connected by a single ligand framework) are used.

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.