112777-69-2

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(4-TRIFLUOROMETHYLPHENYL)-1-PROPANOL is used as a building block for the synthesis of pharmaceuticals, leveraging its unique properties to enhance the development of new drugs.
Used as a Reagent in Asymmetric Synthesis:
(R)-1-(4-TRIFLUOROMETHYLPHENYL)-1-PROPANOL is utilized as a reagent in asymmetric synthesis, a critical process in the production of enantiomerically pure compounds, which are essential for the pharmaceutical industry to ensure the desired biological activity and minimize side effects.
Used as a Precursor in Chiral Ligand Production:
(R)-1-(4-TRIFLUOROMETHYLPHENYL)-1-PROPANOL serves as a precursor in the production of chiral ligands, which are vital for various catalytic processes in the synthesis of enantiomerically pure compounds.
Used as a Solvent in Chemical Reactions:
(R)-1-(4-TRIFLUOROMETHYLPHENYL)-1-PROPANOL is employed as a solvent in chemical reactions, facilitating specific transformations and improving the efficiency of the processes.
Used in Agrochemical and Specialty Chemical Industries:
(R)-1-(4-TRIFLUOROMETHYLPHENYL)-1-PROPANOL is used as an intermediate in the manufacture of agrochemicals and other specialty chemicals, contributing to the development of innovative products in these industries.

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 
• 97-93-8 triethylaluminum 
• 149946-79-2 1-(4'-(trifluoromethyl)phenyl)-allylalcohol 
• 711-33-1 4-trifluoromethyl propiophenone 
• 97-94-9 triethyl borane 

Downstream Products

• 1372175-47-7 (S)-methyl 4-((4-chloro-N-(1-(4-(trifluoromethyl)phenyl)propyl)phenylsulfonamido)methyl)benzoate 
• 306298-15-7 4-Methyl-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-propyl]-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester 
• 306298-16-8 (S)-2-Methyl-4-(4-methyl-piperidin-4-yl)-1-[(S)-1-(4-trifluoromethyl-phenyl)-propyl]-piperazine 
• 306298-13-5 (S)-3-Methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 306298-14-6 (S)-2-Methyl-1-[(S)-1-(4-trifluoromethyl-phenyl)-propyl]-piperazine 
• 306298-12-4 Methanesulfonic acid (R)-1-(4-trifluoromethyl-phenyl)-propyl ester 
• 1372175-48-8 (R)-methyl 4-((4-chloro-N-(1-(4-(trifluoromethyl)phenyl)propyl)phenylsulfonamido)methyl)benzoate 

Relevant academic research and scientific papers

Rationalization of anomalous nonlinear effects in the alkylation of substituted benzaldehydes

Anomalous nonlinear effects in the alkylation of substituted benzaldehydes with diethylzinc using aminoalcohol catalysts are rationalized in terms of a simple extension of the Noyori model to allow for nonthermodynamically controlled partitioning of the c

1,1′-Binaphthylazepine-based ligands for the enantioselective dialkylzinc addition to aromatic aldehydes

The new 1,1′-binaphthylazepine ligand 1c has been prepared and tested in the enantioselective addition of Et2Zn to arylaldehydes, allowing us to reach ee's up to 97% and giving extremely rapid reactions (10-20 min). Aminoalcohol 1c and the analogous compounds 1a and 1b were then tested in the enantioselective addition of Bu2Zn and Me2Zn to arylaldehydes. All of the ligands efficiently catalyze the Bu2Zn addition to benzaldehyde, providing good yields in short reaction times (2-4 h) and high ee (up to 96%). In the enantioselective methylation of arylaldehydes ligands 1b and 1c gave high yields (88-97%) and good to high (80-90%) ee's.

163. Chiral diselenides from benzylamines: Catalysts in the diethylzinc addition to aldehydes

A series of new chiral diselenides with a N-atom in the side chain was prepared by a short synthetic sequence (Scheme 1). Only 1 mol-% of these diselenides catalyzed very effectively the diethylzinc addition to various aromatic and α,β-unsaturated aldehyd

Acetyl-BINOL as mimic for chiral β-diketonates: A building block for new modular ligands

α-Acetyl-(S)-BINOL was prepared by ortho-lithiation and subsequent acetylation of acetal-protected (S)-BINOL. The β-hydroxyketone moiety of this compound is herein a structural mimic for a β-diketonate and forms six-membered chelates with transition metal ions. The second hydroxy-function was submitted to esterification with several carboxylic acids bearing another donor function, thus, new tridentate chiral ligands were obtained. Out of this library the l-proline-α-acetyl-(S)-BINOL-ester was identified to be most effective for the titanium-mediated addition of Et2Zn to PhCHO yielding the respective secondary alcohol with up to 93% ee, which is better than with using (S)-BINOL itself. Besides a solvent dependency (use of MeCN is optimal), the proper choice of the counter-ion is crucial: anion exchange of bromide by trifluoroacetate gave a significant increase of enantioselectivity. Copyright

Rational design of chiral 1,1′-binaphthylazepine-based ligands for the enantioselective addition of ZnEt2 to aromatic aldehydes

By rational design, novel atropisomeric 1,1-binaphthylazepine-based 1,2-amino alcohols 1f and 1g have been prepared in enantiopure form and tested as catalytic precursors in the enantioselective addition of diethylzinc to aromatic aldehydes: the correspon

Novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone

The invention discloses a novel non-metal catalyst for catalyzing asymmetric hydrogenation of ketone and alpha, beta-unsaturated ketone. The preparation method of a chiral alcohol compound shown as formula IV comprises the following step of: reacting a ketone compound shown as formula V with hydrogen under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound to obtain the chiral alcohol compound shown as the formula IV; the preparation method of a chiral tetralone compound shown as formula VI comprises the following step of: under the catalysis of tri(4-hydrotetrafluorophenyl)boron and a chiral oxazoline compound, reacting an alpha, beta-unsaturated ketone compound shown as formula VII with hydrogen to obtain the chiral tetralone compound shown as the formula VI. The method has the advantages of easy synthesis of raw materials, mild reaction conditions, simple operation, high stereoselectivity and the like, the ee value of the product is up to 92%, and the yield is up to 99%.

2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes

A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α′-CF3-diol ligand was highlighted in the ZnII-catalyzed asymmetric ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes. Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcohols in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). As observed from single crystal diffraction analysis, the complexation of the 2,2′-bipyridine-α,α′-CF3-diol ligand generates an unusual hexacoordinated ZnII.

Asymmetric Hydrogenation of Ketones and Enones with Chiral Lewis Base Derived Frustrated Lewis Pairs

The concept of frustrated Lewis pairs (FLPs) has been widely applied in various research areas, and metal-free hydrogenation undoubtedly belongs to the most significant and successful ones. In the past decade, great efforts have been devoted to the synthesis of chiral boron Lewis acids. In a sharp contrast, chiral Lewis base derived FLPs have rarely been disclosed for the asymmetric hydrogenation. In this work, a novel type of chiral FLP was developed by simple combination of chiral oxazoline Lewis bases with achiral boron Lewis acids, thus providing a promising new direction for the development of chiral FLPs in the future. These chiral FLPs proved to be highly effective for the asymmetric hydrogenation of ketones, enones, and chromones, giving the corresponding products in high yields with up to 95 % ee. Mechanistic studies suggest that the hydrogen transfer to simple ketones likely proceeds in a concerted manner.

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands

Abstract: Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.

Observation of hyperpositive non-linear effect in catalytic asymmetric organozinc additions to aldehydes

Asymmetric amplification is a phenomenon that is believed to play a key role in the emergence of homochirality in life. In asymmetric catalysis, theoretical and experimental models have been investigated to provide an understanding of how chiral amplification is possible, in particular based on non-linear effects. Interestingly, it has been proposed a quarter century ago that chiral catalysts, when not enantiopure might even be more enantioselective than their enantiopure counterparts. We show here that such hyperpositive non-linear effect in asymmetric catalysis is indeed possible. An in-depth study into the underlying mechanism was carried out, and the scheme we derive differs from the previous proposed models.