10531-50-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-ALPHA-(TRIFLUOROMETHYL)BENZYL ALCOHOL is used as a chiral building block for the synthesis of pharmaceutical compounds. Its specific stereochemistry allows for the creation of enantiomerically pure drugs, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Synthesis of Mesoporous Metal-Organic Frameworks:
(R)-(-)-ALPHA-(TRIFLUOROMETHYL)BENZYL ALCOHOL is used as a building block in the synthesis of mesoporous metal-organic frameworks (MOFs). These MOFs have potential applications in various fields, such as catalysis, gas storage, and drug delivery, due to their high surface area, tunable pore size, and customizable chemical functionality.
Used in Chemical Research:
(R)-(-)-ALPHA-(TRIFLUOROMETHYL)BENZYL ALCOHOL is used as a research compound in the development of new synthetic methods and the study of reaction mechanisms. Its unique structure allows chemists to explore novel approaches to enantioselective synthesis and gain insights into the factors that influence stereoselectivity in chemical reactions.
Used in Flavor and Fragrance Industry:
(R)-(-)-ALPHA-(TRIFLUOROMETHYL)BENZYL ALCOHOL can be used as a chiral intermediate in the synthesis of flavor and fragrance compounds. The specific enantiomeric form of (R)-(-)-ALPHA-(TRIFLUOROMETHYL)BENZYL ALCOHOL may contribute to the unique scent or taste profile of the final product, making it valuable in the creation of high-quality fragrances and flavorings.

Purification Methods

Purify the chiral alcohols by fractional distillation preferably in a vacuum. [Morrison & Ridgeway Tetrahedron Lett 573 1969, NMR: Pirkle & Beare J Am Chem Soc 90 6250 1968.] The racemate [340-05-6] has b 52-54o/2mm,57-59o/2mm, 64-65o/5mm, d 4 20 1.293, n D 20 1.457, and the 2-carbobenzoyl derivative has m 137-138o [Mosher et al. J Am Chem Soc 78 4374 1956]. [Beilstein 6 IV 3043.]

InChI:InChI=1/C8H7F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5,7,12H/t7-/m1/s1

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 108-05-4 vinyl acetate 
• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 
• 97-72-3 2-Methylpropionic anhydride 
• 123-62-6 propionic acid anhydride 
• 93-97-0 benzoic acid anhydride 
• 100-52-7 benzaldehyde 
• 13652-07-8 phenyltrifluorodiazoethane 
• 557-20-0 diethylzinc 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 124898-12-0 trimethyl[(2,2,2-trifluoro-1-phenylethoxy)]silane 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1445-91-6 (S)-1-phenylethanol 

Downstream Products

• 84877-47-4 trifluoromethanesulfonic acid 2,2,2-trifluoro-1(R)-phenylethyl ester 
• 541515-66-6 Chloro-dimethyl-((R)-2,2,2-trifluoro-1-phenyl-ethoxy)-silane 

Relevant academic research and scientific papers

NAD(P)+-NAD(P)H. 39. Asymmetric Reduction by 1,4-Dihydronicotinamide Derivative Bound to Protein

1,4-Dihydronicotinamide derivatives covalently bound to NH2 or SH group of proteins such as reduced keratin (RK), egg white albumin (EWA), and bovine serum albumin (BSA) have been synthesized and subjected to the reductions of α,α,α-trifluoroacetophenone

Synthesis of Planar Chiral Shvo Catalysts for Asymmetric Transfer Hydrogenation

A new type of planar chiral Shvo catalysts, where the chirality is based solely on different substitution flanking the C￡O function, was prepared and used for transfer hydrogenation of imines and ketones. The reduction of ketimines represented by N-(1-phe

Monitoring surface processes during heterogeneous asymmetric hydrogenation of ketones on a chirally modified platinum catalyst by operando spectroscopy

Surface processes occurring at the catalytic chiral surface of a cinchona-modified Pt catalyst during the asymmetric hydrogenation of activated ketones have been monitored for the first time using operando ATR-IR spectroscopy. Fundamental information about this catalytic system could be gained, including the chiral modification process of the catalyst, the surface interaction of reactant ketone with preadsorbed chiral modifier, the role of hydrogen as well as the influence of the product enantiomers in the catalytic cycle. The formation of a diastereomeric transient surface complex between ketone and chiral modifier was found to be related to the ketone consumption. Among the studied activated ketones, a correlation between stereoselection and the strength of the intermolecular hydrogen bond was identified. Dissociated hydrogen from the catalytic surface is found to play a crucial role in the formation of the diastereomeric surface complex.

Synthesis of a P-stereogenic PNPtBu,Ph ruthenium pincer complex and its application in asymmetric reduction of ketones

A novel P-stereogenic PNPtBu,Ph ruthenium complex has been synthesized and characterized enabling the asymmetric hydrogenation of a wide range of aromatic ketones with excellent catalytic activities (up to 98% conversion) and good levels of enantiodiscrimination (up to 95% ee). P-stereogenic PNPtBu,Ph Ru complex was for the first time synthesized and characterized and has proven to be an efficient catalyst for the asymmetric reduction of a wide range of ketones

Enantioselective reduction of trifluoromethyl ketones using an oxazaborolidine catalyst generated in situ from a chiral lactam alcohol

The oxazaborolidine catalyst prepared in situ from the chiral lactam alcohol 2 and borane was found to catalyze the enantioselective reduction of highly reactive trifluoromethyl ketones at room temperature with high enantioselectivities of up to 86% ee.

Enantioselective hydrosilylation with a chiral N-heterocyclic carbene complex of rhodium(I) [1]

Both enantiomers of the chiral rhodium-NHC complex [(4X, 5X)-1,3-bis[2,6-diisopropyl-phenyl]-4,5-ditert-butylimidazolidine-2-ylidene][1, 5-cyclooctadiene]-iodo-rhodium(I) with X = R, S were applied as catalysts for the asymmetric hydrosilylation of prochi

Electrochemically Promoted Asymmetric Transfer Hydrogenation of 2,2,2-Trifluoroacetophenone

The study reported an electrochemically promoted asymmetric hydrogen transfer reaction of 2,2,2-trifluoroacetophenone with a chiral Ru complex. (R)-α-(Trifluoromethyl) benzyl alcohol with a 96% yield and 94% ee could be obtained with only a 0.5 F mol-1charge amount at room temperature and normal pressure.

Metal-conjugated affinity labels: A new concept to create enantioselective artificial metalloenzymes

How to train a protein: Metal-conjugated affinity labels were used to selectively position catalytically active metal centers in the binding pocket of proteases. The resulting artificial metalloenzymes achieve up to 82% e.r. in the hydrogenation of ketone

Enantioselective hydrogenation of ketones by iridium nanoparticles ligated with chiral secondary phosphine oxides

Chiral iridium nanoparticles (IrNPs) were synthesized by H2 reduction of (1,5-cyclooctadiene)(methoxy)iridium(i) dimer ([Ir(OMe)(COD)]2) in the presence of an asymmetric secondary phosphine oxide (4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′

Origin of the rate enhancement and enantiodifferentiation in the heterogeneous enantioselective hydrogenation of 2,2,2-trifluoroacetophenone over Pt/alumina studied in continuous-flow fixed-bed reactor system

A study on the origin of rate enhancement and enantiodifferentiation in the enantioselective hydrogenation of 2,2,2-trifluoroacetophenone (TFAP) over a Pt/alumina catalyst modified by cinchona alkaloids in toluene/acetic acid (AcOH) solvent mixture with a