24654-53-3

Usage

Type of compound

nitrile compound containing a trifluoromethylphenyl group

Uses

building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds; production of polymers and industrial chemicals

Safety precautions

potential toxicity and reactivity, requires proper handling and safety measures

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 75-05-8 acetonitrile 
• 1813-97-4 1-allyl-4-(trifluoromethyl)benzene 
• 773837-37-9 sodium cyanide 
• 131356-53-1 1-(2,2-dibromovinyl)-4-(trifluoromethyl)benzeney 
• 13635-04-6 3-hydroxy-3-methylbutyronitrile 
• 455-13-0 4-Iodobenzotrifluoride 
• 107-13-1 acrylonitrile 
• 42006-43-9 (E)-1-(prop-1-en-1-yl)-4-(trifluoromethyl)benzene 
• 764-42-1 1,2-Dicyanoethylene 
• 952739-61-6 (E)-1-(2-iodovinyl)-4-(trifluoromethyl)-benzene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 125617-18-7 3-(4-trifluoromethylphenyl)-2-propen-1-ol 
• 101466-85-7 ethyl (E)-4-trifluoromethylcinnamate 

Downstream Products

• 107234-85-5 erythro-4-cyano-3-(4-trifluoromethylphenyl)-2-phenylbutanoate d'ethyle 
• 107235-01-8 trans-4-(4-trifluoromethylphenyl)-3-phenylpiperidin-2-one 
• 107235-01-8 cis-4-(4-trifluoromethylphenyl)-3-phenylpiperidin-2-one 
• 57103-25-0 cis-3-(4-(trifluoromethyl)phenyl)acrylonitrile 

Relevant academic research and scientific papers

Arylcyanation of norbornene and norbornadiene catalyzed by nickel

Aryl cyanides add to norbornene and norbornadiene under nickel catalysis to give (2R*,3S*)-3-aryl-2-cyanobicyclo[2.2.1]-heptanes and (2R*,3S*)-3-aryl-2-cyanobicyclo[2.2.1]hept-5-enes in good yields with a general substrate scope. On the other hand, the re

Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction

A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.

Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates

The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set-up using NaDA (sodium diisopropylamide) in EtNMe2 or NaTMP (sodium 2,2,6,6-tetramethylpiperidide)?TMEDA in n-hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized acrylonitriles and alkenyl sulfides. This flow-procedure was successfully extended to other acrylates by using Barbier-type conditions.

E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis

Nitriles are found in many bioactive compounds, and are among the most versatile functional groups in organic chemistry. Despite many notable recent advances, however, there are no approaches that may be used for the preparation of di- or tri-substituted alkenyl nitriles. Related approaches that are broad in scope and can deliver the desired products in high stereoisomeric purity are especially scarce. Here, we describe the development of several efficient catalytic cross-metathesis strategies, which provide direct access to a considerable range of Z- or E-di-substituted cyano-substituted alkenes or their corresponding tri-substituted variants. Depending on the reaction type, a molybdenum-based monoaryloxide pyrrolide or chloride (MAC) complex may be the optimal choice. The utility of the approach, enhanced by an easy to apply protocol for utilization of substrates bearing an alcohol or a carboxylic acid moiety, is highlighted in the context of applications to the synthesis of biologically active compounds.

Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: Chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles

A copper-catalyzed transfer aldol type reaction of β-hydroxy ketones or nitriles with aldehydes is reported, which enables chemo- and stereoselective access to (E)-α,β-unsaturated ketones and (E)-acrylonitriles. A key step of the in situ copper(i)-promoted retro-aldol reaction of β-hydroxy ketones or nitriles is proposed to generate a reactive Cu(i) enolate or cyanomethyl intermediate, which undergoes ensuing aldol condensation with aldehydes to deliver the products. This reaction uses 1.2 mol% Cu(IPr)Cl (IPr denotes 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) as the catalyst in the presence of 6.0 mol% NaOtBu cocatalyst at room temperature or 70 °C. A range of aryl and heteroaryl aldehydes as well as acrylaldehydes are compatible with many useful functional groups being tolerated. Under the mild and weakly basic conditions, competitive Cannizzaro-type reaction of benzaldehydes and side reactions of base-sensitive functional groups can be effectively suppressed, which show synthetic advantages of this reaction compared to classic aldol reactions. The synthetic potential of this reaction is further demonstrated by the one-step synthesis of biologically active quinolines and 1,8-naphthyridine in excellent yields (up to 91%). Finally, a full catalytic cycle for this reaction has been constructed using DFT computational studies in the context of a retro-aldol/aldol two-stage mechanism. A rather flat reaction energy profile is found indicating that both stages are kinetically facile, which is consistent with the mild reaction conditions.

CUCN-MEDIATED ONE POT PRODUCTION OF CINNAMONITRILE DERIVATIVES

The present invention discloses a cheaper and practical protocol for the construction of a wide variety of o-cyanocin-namonitrile and their structural analogues that proceeds with good yields in a single step using CuCN as the only reagent.

Cu-catalyzed debrominative cyanation of gem-dibromoolefins: A facile access to α,β-unsaturated nitriles

An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, l-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62-86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.

CUCN-MEDIATED ONE POT PRODUCTION OF CINNAMONITRILE DERIVATIVES

The present invention discloses a cheaper and practical protocol for the construction of a wide variety of o-cyanocinnamonitrile and their structural analogues that proceeds with good yields in a single step using CuCN as the only reagent.

A novel oxidative transformation of alcohols to nitriles: An efficient utility of azides as a nitrogen source

An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN3 as a source of nitrogen in the presence of a catalytic amount of Cu(ClO4)2·6H 2O.

Iron-facilitated direct oxidative C-H transformation of allylarenes or alkenes to alkenyl nitriles

This paper describes the first direct approach to alkenyl nitriles from allylarenes or alkenes facilitated by an inexpensive homogeneous iron catalyst. Three C-H bond cleavages occur under the mild conditions during this process. Mechanistic studies indic