403-40-7

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-FLUOROPHENYL)ETHYLAMINE is used as a synthetic intermediate for the development of novel thioureas with diuretic and saluretic activity. Its application in this field is due to its ability to participate in nucleophilic substitution reactions, which are crucial for the synthesis of these therapeutic agents.
Used in Chemical Synthesis:
1-(4-FLUOROPHENYL)ETHYLAMINE is used as a reagent in various chemical synthesis processes. Its nucleophilic substitution reactions make it a valuable component in creating new compounds with potential applications in different industries.

InChI:InChI=1/C8H7FO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3

Upstream product

• 329-79-3 1-(4-fluorophenyl)ethanone oxime 
• 75-05-8 acetonitrile 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 66399-30-2 (S)-1-(4-Fluoro-phenyl)-ethylamine 
• 405-99-2 para-fluorostyrene 
• 1559065-84-7 N-chloro-1-(4-fluorophenyl)ethanimine 
• 48108-93-6 β-(o-aminophenyl)ethylamine 

Downstream Products

• 56000-55-6 2-[1-(4-Fluoro-phenyl)-ethylamino]-2-[(Z)-hydroxyimino]-N,N-dimethyl-acetamide 
• 66399-30-2 (S)-1-(4-Fluoro-phenyl)-ethylamine 
• 91941-06-9 N⁶-[1-(4-Fluoro-phenyl)-ethyl]-3-nitro-pyridine-2,6-diamine 
• 183797-20-8 C₁₆H₂₇FNP 

Relevant academic research and scientific papers

General and selective synthesis of primary amines using Ni-based homogeneous catalysts

The development of base metal catalysts for industrially relevant amination and hydrogenation reactions by applying abundant and atom economical reagents continues to be important for the cost-effective and sustainable synthesis of amines which represent highly essential chemicals. In particular, the synthesis of primary amines is of central importance because these compounds serve as key precursors and central intermediates to produce value-added fine and bulk chemicals as well as pharmaceuticals, agrochemicals and materials. Here we report a Ni-triphos complex as the first Ni-based homogeneous catalyst for both reductive amination of carbonyl compounds with ammonia and hydrogenation of nitroarenes to prepare all kinds of primary amines. Remarkably, this Ni-complex enabled the synthesis of functionalized and structurally diverse benzylic, heterocyclic and aliphatic linear and branched primary amines as well as aromatic primary amines starting from inexpensive and easily accessible carbonyl compounds (aldehydes and ketones) and nitroarenes using ammonia and molecular hydrogen. This Ni-catalyzed reductive amination methodology has been applied for the amination of more complex pharmaceuticals and steroid derivatives. Detailed DFT computations have been performed for the Ni-triphos based reductive amination reaction, and they revealed that the overall reaction has an inner-sphere mechanism with H2metathesis as the rate-determining step.

Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

Thirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against Oomycete fungi Phytophthora capsici in vitro and in vivo. Interestingly, compound I-1, I-2, I-3, I-6 and I-7 exhibited moderate control effect (>50%) against Pseudoperonospora cubensis in greenhouse at 6.25 μg/mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against P. capsici. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against Sclerotinia sclerotiorum, P. piricola and R. solan in vitro with EC50 values of 3.74–9.76 μg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides.

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.

Small molecule compound for overcoming EGFR drug resistance mutation as well as preparation method and application of small molecule compound

The invention belongs to the field of chemical medicines and specifically relates to a small molecule compound for overcoming EGFR drug resistance mutation. The small molecule compound has a formula as shown in the specification. The small molecule compound provided by the invention has a good inhibition effect on an H1975 cell strain with EGFRT790M mutation in vitro, that is, a part of moleculeshave median inhibitory concentrations up to a nanomole grade level upon H1975, is small in toxicity, has IC50 of 10 [mu]M or greater upon most cell strains except the H1975, has good selectivity, doesnot directly inhibit the activity of the EGFR, is capable of avoiding compound drug resistance caused by drug resistance mutation, provides novel effective options for development and preparation ofa new generation of EGFRT790M drug resistant small molecule target medicines, and has good development prospects.

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.

A Comprehensive Quantitative Assay for Amine Transaminases

The development of effective high-throughput screening assays has contributed greatly to the wealth of designer enzymes available, by enabling rapid identification of desired variants from large mutant libraries. Here, we report a general and operationally simple end-point assay for transaminases that enables the screening of both amine donors and acceptors in liquid phase. The spectrophotometric-based screen exploits the amine donor 2-aminoethylaniline (2-AEA) and relies on reaction of in situ generated indole with Ehrlich's reagent. The assay has also been adapted to allow screening in the reverse direction by addition of indole and subsequent spectrophotometric analysis. Importantly, the screen provides qualitative information on the enantio-preference of the individual biocatalysts. To increase the assay throughput, an engineered expression strain (E. coli BL21(DE3) ΔtnaA) lacking tryptophanase activity, was generated to enable reliable and direct evaluation of individual colonies arrayed on agar plates.