3047-99-2

Usage

Uses

Used in Organic Synthesis:
4-(TRIFLUOROMETHYL)BENZYLAMINE is utilized as a key building block in organic synthesis for the creation of a wide array of chemical compounds. Its unique structure allows for the formation of diverse molecular architectures, which are essential in the development of new materials and pharmaceutical agents.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(TRIFLUOROMETHYL)BENZYLAMINE is employed as a precursor in the synthesis of potential new drugs. Its incorporation into drug molecules can impart specific pharmacological properties, such as enhanced potency, selectivity, or bioavailability, making it a valuable component in drug discovery and development processes.
Used in Agrochemical Development:
4-(TRIFLUOROMETHYL)BENZYLAMINE also finds application in the agrochemical sector, where it serves as a starting material for the synthesis of novel agrochemicals. Its use in this field contributes to the development of more effective and environmentally friendly pesticides, herbicides, and other agricultural chemicals.
Used as a Ligand in Coordination Chemistry:
Furthermore, 4-(TRIFLUOROMETHYL)BENZYLAMINE functions as a ligand in the coordination chemistry of transition metal complexes. Its ability to form stable complexes with various metal ions is exploited in the design of catalysts, sensors, and materials with specialized properties for applications in catalysis, molecular recognition, and other areas of chemistry.

Upstream product

• 455-18-5 4-CF₃C₆H₄CN 
• 41360-55-8 2-[(4-trifluoromethyl)phenyl]acetamide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 3300-51-4 p-Trifluoromethylbenzylamine 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 
• 1891-90-3 p-trifluoromethylbenzamide 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 1098339-79-7 1-(nitromethyl)-4-(trifluoromethyl)benzene 
• 66046-34-2 4-(trifluoromethyl)benzaldehyde oxime 

Downstream Products

• 124426-49-9 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide 
• 1173565-45-1 (3R,4S)-tert-butyl 4-((4-(1-allyl-3-(4-(trifluoromethyl)benzyl)ureido)piperidin-1-yl)methyl)-3-hydroxy-3-phenylpyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

N-Heterocyclic Carbene-Phosphinidenide Complexes as Hydroboration Catalysts

The reactions of the N-heterocyclic carbene-phosphinidene adducts (NHC)PSiMe3 and (NHC)PH with the dinuclear ruthenium and osmium complexes [(η6-p-cymene)MCl2]2 (M = Ru, Os) afforded the half-sandwich complexes

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

Method for preparing amine compound by reducing amide compound

The invention relates to a method for preparing an amine compound by reducing an amide compound, which comprises the following steps: in a protective atmosphere, mixing the amide compound or cyclic amide, a zirconium metal catalyst and pinacol borane, carrying out amide reduction reaction at room temperature, and carrying out aftertreatment by using an ether solution of hydrogen chloride after 12-48 hours to obtain an amine hydrochloride compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate range.

Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds

AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Metal-Free Synthesis of Heteroaryl Amines or Their Hydrochlorides via an External-Base-Free and Solvent-Free C-N Coupling Protocol

Herein, a metal-free and solvent-free protocol was developed for the C-N coupling of heteroaryl halides and amines, which afforded numerous heteroaryl amines or their hydrochlorides without any external base. Further investigations elucidated that the basicity of amines and specific interactions derived from the X-ray crystallography analysis of 3j′·HCl played pivotal roles in the reactions. Moreover, this protocol was scalable to gram scales and applicable to drug molecules, which demonstrated its practical value for further applications.

Base-Catalyzed Hydrosilylation of Nitriles to Amines and Esters to Alcohols

Base-catalyzed hydrosilylation of nitriles to amines and esters to silylated alcohols is reported. This protocol tolerates electron-rich and electron-neutral olefins and works in the presence of basic functional groups (e. g. tertiary amines) but fails for acidic substrates, such as phenols and NH anilines. This catalytic system does not tolerate carbonyl groups, such as aldehydes, ketones, esters and carbamides, which are reduced to corresponding alcohols and amines. With the exact amount of silane, esters can be selectively reduced in the presence of nitriles, but the selectivity drops for the pairs ester/carboxamide and carboxamide/nitrile. Through competition experiments, the following preference in functional group reactivity was determined: ester > carboxamide > nitrile.

Green method for catalyzing reduction reaction of aliphatic nitro derivative

The invention relates to a green method for catalyzing reduction reaction of aliphatic nitro derivatives. According to the method, non-transition metal compounds, namely triethyl boron and potassium tert-butoxide, are used as a catalytic system for the first time, an aliphatic nitro derivative and pinacolborane which is low in price and easy to obtain are catalyzed to be subjected to a reduction reaction under mild conditions, and an aliphatic amine hydrochloride product is synthesized after acidification with a hydrochloric acid aqueous solution. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient, and reaction is safe. The selective reduction reaction of the aliphatic nitro derivative catalyzed by the non-transition metal catalyst and pinacol borane is realized for the first time, and the aliphatic amine hydrochloride product is synthesized through acidification treatment of the hydrochloric acid aqueous solution, so that a practical new reaction strategy is provided for laboratory preparation or industrial production.

A cobalt phosphide catalyst for the hydrogenation of nitriles

The study of metal phosphide catalysts for organic synthesis is rare. We present, for the first time, a well-defined nano-cobalt phosphide (nano-Co2P) that can serve as a new class of catalysts for the hydrogenation of nitriles to primary amines. While earth-abundant metal catalysts for nitrile hydrogenation generally suffer from air-instability (pyrophoricity), low activity and the need for harsh reaction conditions, nano-Co2P shows both air-stability and remarkably high activity for the hydrogenation of valeronitrile with an excellent turnover number exceeding 58000, which is over 20- to 500-fold greater than that of those previously reported. Moreover, nano-Co2P efficiently promotes the hydrogenation of a wide range of nitriles, which include di- and tetra-nitriles, to the corresponding primary amines even under just 1 bar of H2 pressure, far milder than the conventional reaction conditions. Detailed spectroscopic studies reveal that the high performance of nano-Co2P is attributed to its air-stable metallic nature and the increase of the d-electron density of Co near the Fermi level by the phosphidation of Co, which thus leads to the accelerated activation of both nitrile and H2. Such a phosphidation provides a promising method for the design of an advanced catalyst with high activity and stability in highly efficient and environmentally benign hydrogenations. This journal is

Non-Pincer Mn(I) Organometallics for the Selective Catalytic Hydrogenation of Nitriles to Primary Amines

We report herein selective catalytic hydrogenation of nitriles to primary amines with the use of the non-pincer Mn(I) compound fac-[(CO)3Mn{iPr2P(CH2)2PiPr2}(OTf)] (2) as a catalytic precursor (3 mol %) in the presence of KOtBu (10 mol %) and 2-BuOH as solvent. Benchmark benzonitrile and electron-rich aromatic and aliphatic nitriles were hydrogenated under rather mild conditions (7 bar, 90 °C, 15 min) to produce the corresponding amines in excellent to very good isolated yields (83-97%, six examples). Increasing the H2 pressure and time (35 bar, 30 min) allowed for the production of (di)amines in excellent yields (94-98%, three examples) from electron-deficient aromatic nitriles and terephthalonitrile. Notably, adiponitrile was reduced to hexamethylenediamine in 53% isolated yield. Finally, mechanistic insights were performed and suggested unsaturated Mn-hydride species performing the elementary steps during catalytic turnover.