24358-62-1

Usage

Uses

Used in Chemical Synthesis Studies:
4-Bromo-alpha-phenethylamine is used as a synthetic intermediate for the production of various pharmaceuticals and other organic compounds. Its unique chemical structure allows it to be a versatile building block in the synthesis of a wide range of molecules, making it a valuable asset in the field of organic chemistry.
Used in Pharmaceutical Research:
4-Bromo-alpha-phenethylamine is used as a research compound in the development of new drugs, particularly those targeting the central nervous system. Its structural similarity to certain neurotransmitters and its reactivity make it a promising candidate for the design of novel therapeutic agents.
Used in Material Science:
In the field of material science, 4-Bromo-alpha-phenethylamine can be used as a dopant or additive to modify the properties of various materials. Its ability to interact with other molecules and its reactivity can lead to the development of new materials with improved characteristics.
Used in Analytical Chemistry:
4-Bromo-alpha-phenethylamine can also be employed as a reference compound or standard in analytical chemistry. Its distinct chemical properties make it useful for calibrating instruments and validating analytical methods, ensuring accurate and reliable results in chemical analyses.

InChI:InChI=1/C8H10BrN/c1-6(10)7-2-4-8(9)5-3-7/h2-6H,10H2,1H3/p+1/t6-/m1/s1

Upstream product

• 59862-55-4 p-bromoacetophenone oxime 
• 99-90-1 para-bromoacetophenone 
• 77287-34-4 formamide 
• 70242-28-3 1-(4-bromophenyl)ethanone O-methyl oxime 
• 75230-51-2 4-bromoacetophenone tosylhydrazone 
• 101422-65-5 2-[1-(4-bromophenyl)ethyl]isoindoline-1,3-dione 
• 68006-62-2 N-Formyl<1-(4-bromophenyl)ethyl>amin 
• 16712-16-6 ammonium formate 
• 220441-76-9 (R)-2-(4-Bromo-phenyl)-4-phenyl-oxazolidine 
• 1122-91-4 4-bromo-benzaldehyde 
• 99-73-0 para-bromophenacyl bromide 
• 71426-51-2 anti-α,4'-dibromoacetophenone oxime 
• 1434603-04-9 (Z)-1-(4-bromophenyl)ethanone O-benzyloxime 
• 1585-07-5 1-bromo-4-ethylbenzene 

Downstream Products

• 7644-04-4 4-bromophenacylamine 
• 6114-67-6 [1-(4-bromo-phenyl)-ethyl]-cyclohexylidene-amine 
• 133175-52-7 (R)-N-[(S)-1-(4-Bromo-phenyl)-ethyl]-2-fluoro-2-phenyl-acetamide 
• 133175-36-7 (R)-N-[(R)-1-(4-Bromo-phenyl)-ethyl]-2-fluoro-2-phenyl-acetamide 
• 24358-62-1 1-(4-Bromo-phenyl)-ethylamine 
• 24358-62-1 1-(4-Bromo-phenyl)-ethylamine 
• 27298-97-1 (S)-1-(4-bromophenyl)ethylamine 
• 24358-62-1 (R)-1-(4-bromophenyl)ethylamine 
• 177750-53-7 N-[(1R)-1-(4-bromophenyl)ethyl]acetamide 
• 353235-89-9 N-(1-(4-bromophenyl)ethyl)pyrid-3-ylmethylamine 
• 843647-56-3 C₁₅H₂₁BrN₂O₃ 
• 850363-42-7 1-(4-bromophenyl)-N-(tert-butoxycarbonyl)ethylamine 
• 389602-48-6 N-[1-(4-bromophenyl)ethyl]-3-(biphenyl-2-carbonylamino)-benzoic acid amide 

Relevant academic research and scientific papers

Enhancing thermostability and organic solvent tolerance of ω-transaminase through global incorporation of fluorotyrosine

Here, we have utilized the incorporation of non-canonical amino acids as a tool kit to improve enzyme properties for organic synthesis applications. The global incorporation of 3-fluorotyrosine (FY) into ω-transaminase (ω-TA) to give ω-TA[FY] enhanced the thermostability and organic solvent tolerance without altering substrate specificity and enantioselectivity. Moreover, ω-TA[FY] was able to completely convert 25 mM of acetophenone into (S)-1-phenylethylamine (ee>99%) in the presence of 20% DMSO (v/v) which is 2-fold higher when compared to wild-type ω-TA.

Synthesis method of garafloxacin intermediate

The invention discloses a synthesis method of a garafloxacin intermediate (1R)-5-bromo-2, 3-dihydro-1-methyl-1H-isoindole; the synthesis method comprises the following steps of: taking a garafloxacin intermediate as a raw material; the method comprises the following steps: step 1, by taking R(+)-alpha-phenylethylamine as a raw material and lewis acid as a catalyst, carrying out bromine bromination reaction to obtain a compound 2; 2, placing the compound 2 in a solvent, adding hydrochloric acid, paraformaldehyde and a catalyst, and carrying out chloromethylation reaction to obtain a compound 3; 3, dissolving the compound 3 in a solvent, adding alkali, and heating the mixture for reaction to obtain a compound 1. The method is simple in reaction, short in route, less in three wastes, environment-friendly, high in yield of each step, less in waste of raw materials and reagents, and especially suitable for industrial production.

Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant

The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.

The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst

The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth-abundant metals is similarly appealing. Here, the iron-catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N-doped SiC material as catalyst support.

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions

The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).

Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

Rh(III)-Catalyzed Coupling of N-Chloroimines with α-Diazo-α-phosphonoacetates for the Synthesis of 2 H-Isoindoles

We report herein the first use of N-chloroimines as effective synthons for directed C-H functionalization. Rh(III)-catalyzed coupling of N-chloroimines with α-diazo-α-phosphonoacetates allows for efficient dechlorinative/dephosphonative access to 2H-isoindoles. Further deesterification under Ni(II) catalysis enables the complete elimination of reactivity-assisting groups and full exposure of reactivity of C3 and N2 ring atoms for attaching structurally distinct appendages.

Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2

A ruthenium/C3-TunePhos catalytic system has been identified for highly efficient direct reductive amination of simple ketones. The strategy makes use of ammonium acetate as the amine source and H2 as the reductant and is a user-friendly and operatively simple access to industrially relevant primary amines. Excellent enantiocontrol (>90% ee for most cases) was achieved with a wide range of alkyl aryl ketones. The practicability of this methodology has been highlighted by scalable synthesis of key intermediates of three drug molecules. Moreover, an improved synthetic route to the optimal diphosphine ligand C3-TunePhos is also presented.

Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization

In recent years, the reductive amination of ketones in the presence of amine dehydrogenases emerged as an attractive synthetic strategy for the enantioselective preparation of amines starting from ketones, an ammonia source, a reducing reagent and a cofactor, which is recycled in situ by means of a second enzyme. Current challenges in this field consists of providing a broad synthetic platform as well as process development including enzyme immobilization. In this contribution these issues are addressed. Utilizing the amine dehydrogenase EsLeuDH-DM as a mutant of the leucine dehydrogenase from Exigobacterium sibiricum, a range of aryl-substituted ketones were tested as substrates revealing a broad substrate tolerance. Kinetics as well as inhibition effects were also studied and the suitability of this method for synthetic purpose was demonstrated with acetophenone as a model substrate. Even at an elevated substrate concentration of 50 mM, excellent conversion was achieved. In addition, the impact of water-miscible co-solvents was examined, and good activities were found when using DMSO of up to 30% (v/v). Furthermore, a successful immobilization of the EsLeuDH-DM was demonstrated utilizing a hydrophobic support and a support for covalent binding, respectively, as a carrier.

Substituent effects on chiral resolutions of derivatized 1-phenylalkylamines by heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin GC stationary phase

Chiral resolutions of trifluoroacetyl-derivatized 1-phenylalkylamines with different type and position of substituent were investigated by capillary gas chromatography by using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin diluted in OV-1701 as a chiral stationary phase. The influence of column temperature on retention and enantioselectivity was examined. All enantiomers of meta-substituted analytes as well as fluoro-substituted analytes could be resolved. Temperature had a favorable influence on enantioselectivity for small amines with substituents at the ortho-position. The type of substituent at the stereogenic center of amines also had a crucial effect as the ethyl group led to poor enantioseparation. Among all analytes studied, trifluoroacetyl-derivatized 1-(2′-fluorophenyl)ethylamine exhibited baseline resolution with the shortest analysis time.