74877-08-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(3'-BROMOPHENYL)ETHYLAMINE is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new medicinal compounds. Its unique structure allows it to be a key component in creating a variety of drugs with different therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(3'-BROMOPHENYL)ETHYLAMINE is utilized as an intermediate in the production of agrochemicals, playing a role in the synthesis of compounds that can be used in pest control, crop protection, and other agricultural applications.
Used in Organic Chemistry Research:
1-(3'-BROMOPHENYL)ETHYLAMINE serves as a building block in the preparation of new chemical entities for various applications within organic chemistry. Its distinctive structure makes it a valuable component in the exploration and creation of novel organic compounds for research and development purposes.

Upstream product

• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 1214919-61-5 C₉H₁₀BrNO 
• 52780-14-0 1-(3-bromophenyl)ethanol 
• 139305-97-8 1-((S)-1-Azido-ethyl)-3-bromo-benzene 
• 185527-32-6 N-[(S)-1-(3-Bromo-phenyl)-ethyl]-oxalamic acid octyl ester 
• 687-47-8 (S)-Ethyl lactate 
• 623-50-7 ethyl 2-hydroxyacetate 
• 95-92-1 oxalic acid diethyl ester 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 3938-96-3 ethyl 2-methoxyacetate 
• 52780-14-0 (R)-1-(3-bromophenyl)ethanol 
• 24280-05-5 N-[1-(3-bromophenyl)ethylidene]hydroxyl amine 
• 110-60-1 1,4-diaminobutane 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 

Downstream Products

• 74877-08-0 (S)-1-(3-bromophenyl)ethanamine 
• 176707-77-0 (R)-N-[1-(3-bromophenyl)ethyl] acetamide 
• 177750-52-6 (S)-N-(1-(3-bromophenyl)ethyl)acetamide 
• 185527-32-6 N-[(S)-1-(3-Bromo-phenyl)-ethyl]-oxalamic acid octyl ester 
• 375853-98-8 [1-(3-bromophenyl)ethyl]-carbamic acid tert-butyl ester 
• 903556-58-1 C₁₆H₁₆BrNO₂ 
• 903580-85-8 N-(1-(3-bromophenyl)ethyl)-5-fluoro-2-nitrobenzenamine 
• 1255924-84-5 2-(1-(3-bromophenyl)ethylamino)-1-(4-chlorophenyl)ethanone 
• 1418316-42-3 C₁₅H₁₄BrNO 
• 1439400-36-8 C₁₉H₂₉NO₄ 
• 1439400-38-0 C₁₅H₂₁NO₄ 

Relevant academic research and scientific papers

Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(iii) complexes bearing an amidato ligand

A series of half-sandwich Ir(iii) complexes1-6bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex1, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Asymmetric transformation was also attempted with chiral Ir complexes3-6, and 16% ee of the desired primary amine was obtained. Despite the unsatisfactory enantio-control achieved so far, the current exploration might stimulate more efforts towards the discovery of better chiral catalysts for this challenging but important transformation.

One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines

An efficient method has been developed for the synthesis of seven-membered biaryl lactams involving Pd-catalyzed, native amine-directed, ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized coupling partner is also explored, as is the potential for synthesizing eight-membered biaryl lactams. Various applications are also investigated, including access to the aza-brassinolide core.

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.

Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines

C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.

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.

n-Butylamine as an alternative amine donor for the stereoselective biocatalytic transamination of ketones

Formal reductive amination has been a main focus of biocatalysis research in recent times. Among the enzymes able to perform this transformation, pyridoxal-5′-phosphate-dependent transaminases have shown the greatest promise in terms of extensive substrate scope and industrial application. Despite concerted research efforts in this area, there exist relatively few options regarding efficient amino donor co-substrates capable of allowing high conversion and atom efficiency with stable enzyme systems. Herein we describe the implementation of the recently described spuC gene, coding for a putrescine transaminase, exploiting its unusual amine donor tolerance to allow use of inexpensive and readily-available n-butylamine as an alternative to traditional methods. Via the integration of SpuC homologues with tandem co-product removal and cofactor regeneration enzymes, high conversion could be achieved with just 1.5 equivalents of the amine with products displaying excellent enantiopurity.

Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases

A one-pot/two-step bienzymatic asymmetric amination of secondary alcohols is disclosed. The approach is based on a sequential strategy involving the use of a laccase/TEMPO catalytic system for the oxidation of alcohols into ketone intermediates, and their following transformation into optically enriched amines by using transaminases. Individual optimizations of the oxidation and biotransamination reactions have been carried out, studying later their applicability in a concurrent process. Therefore, 17 racemic (hetero) aromatic sec-alcohols with different substitutions in the aromatic ring have been converted into enantioenriched amines with good to excellent selectivities (90-99% ee) and conversion values (67-99%). The scalability of the process was also demonstrated when two different amine donors were used in the transamination step, such as isopropylamine and cis-2-buten-1,4-diamine. Satisfyingly, both sacrificial amine donors can shift the equilibrium toward the amine formation, leading to the corresponding isolated enantioenriched amines with good to excellent results.

Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases

The discovery and characterisation of enzymes with both monoamine and diamine transaminase activity is reported, allowing conversion of a wide range of target ketone substrates with just a small excess of amine donor. The diamine co-substrates (putrescine, cadaverine or spermidine) are bio-derived and the enzyme system results in very little waste, making it a greener strategy for the production of valuable amine fine chemicals and pharmaceuticals.

Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists

We report the first comprehensive structure-activity study of calindol (4, (R)-N-[(1H-indol-2-yl)methyl]-1-(1-naphthyl)ethanamine), a positive allosteric modulator, or calcimimetic, of the calcium sensing receptor (CaSR). While replacement of the naphthyl moiety of calindol by other aromatic groups (phenyl, biphenyl) was largely detrimental to calcimimetic activity, incorporation of substituents on the 4, 5 or 7 position of the indole portion of calindol was found to provide either equipotent derivatives compared to calindol (e.g., 4-phenyl, 4-hydroxy, 5-hydroxycalindol 44, 52, 53) or, in the case of 7-nitrocalindol (51), a 6-fold more active calcimimetic displaying an EC50 of 20 nM. Unlike calindol, the more active CaSR calcimimetics were shown not to act as antagonists of the closely related GPRC6A receptor, suggesting a more selective profile for these new analogues.

Bioinspired organocatalytic aerobic C-H oxidation of amines with an ortho -quinone catalyst

A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of α-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.