330-72-3

Usage

Uses

Used in Pharmaceutical Research and Development:
1,1,1-Trifluoro-3-phenylpropan-2-ol is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Production:
1,1,1-TRIFLUORO-3-PHENYLPROPAN-2-OL is also utilized in the production of agrochemicals, contributing to the development of innovative and effective solutions for crop protection and pest management.
Used in Specialty and Fine Chemicals Synthesis:
1,1,1-Trifluoro-3-phenylpropan-2-ol is employed as a building block in the synthesis of specialty and fine chemicals, which are used in a variety of applications, including fragrances, flavors, and other high-value products.
Safety Precautions:
Due to its flammability and potential health hazards, it is crucial to handle and store 1,1,1-trifluoro-3-phenylpropan-2-ol with proper safety measures. This includes using appropriate personal protective equipment, ensuring proper ventilation, and following established safety protocols to minimize risks associated with its use.

Upstream product

• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 6921-34-2 benzylmagnesium chloride 
• 350-92-5 1,1,1-Trifluoro-3-phenylpropan-2-one 
• 359-41-1 1,1,1-trifluoro-2,3-epoxypropane 
• 71-43-2 benzene 
• 122-78-1 phenylacetaldehyde 
• 130025-34-2 (S)-2-trifluoromethyl-oxirane 
• 100-58-3 phenylmagnesium bromide 
• 121960-70-1 (2S,3R)-1,1,1-Trifluoro-3-phenyl-3-((R)-toluene-4-sulfinyl)-propan-2-ol 
• 115878-92-7 (S)-1,1,1-Trifluoro-3-phenyl-3-((S)-toluene-4-sulfinyl)-propan-2-one 
• 121898-30-4 (2S,3R)-1,1,1-Trifluoro-3-phenyl-3-p-tolylsulfanyl-propan-2-ol 
• 121898-12-2 (2R,3S)-1,1,1-Trifluoro-3-phenyl-3-((R)-toluene-4-sulfinyl)-propan-2-ol 
• 121898-17-7 (2R,3S)-1,1,1-Trifluoro-3-phenyl-3-p-tolylsulfanyl-propan-2-ol 
• 112-31-2 caprinaldehyde 

Downstream Products

• 350-92-5 1,1,1-Trifluoro-3-phenylpropan-2-one 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands

The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.

Unveiling the Hidden Performance of Whole Cells in the Asymmetric Bioreduction of Aryl-containing Ketones in Aqueous Deep Eutectic Solvents

In this contribution, we report the first successful baker's yeast reduction of arylpropanones using deep eutectic solvents (DESs) as biodegradable and non-hazardous co-solvents. The nature of DES [e.g. choline chloride/glycerol (2:1)] and the percentage of water in the mixture proved to be critical for both the reversal of selectivity and to achieve high enantioselectivity on going from pure water (up to 98:2 er in favour of the S-enantiomer) to DES/aqueous mixtures (up to 98:2 er in favour of the R-enantiomer). As a result, both enantiomers of valuable chiral alcohols of pharmaceutical interest were prepared from the same biocatalyst by simply switching the solvent. The possible inhibition of some (S)-oxidoreductases making part of the genome of such a wild-type whole cell biocatalyst when DESs are used as co-solvents may pave the way for an anti-Prelog reduction. The scope and limitations of this kind of biotransformations for a range of aryl-containing ketones are also discussed. (Figure presented.).

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines

In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction

Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions

The versatility of Kluyveromyces marxianus CBS 6556 growing cells in the enantioselective reduction of ketone functionalities to the corresponding alcohols was exploited. In particular, methyl ketones were reduced to (S)-alcohols with ees of up to 96%. Longer chain alkyl ketones afforded, under the same experimental condition, (R)-alcohols with an ee of up to 84%. Interestingly, carbon-carbon double and the triple bonds can also be reduced in the presence of Kluyveromyces marxianus CBS 6556 yeast. A cyclic ketone, such as 2-tetralone, was also quantitatively reduced to its corresponding (S)-alcohol with ee = 76%.

Synthesis of trifluoromethyl alcohols from tert-butoxy-β-(trifluoromethyl)styrenes and trifluoromethylbenzyl ketones under the conditions of the Leuckart-Wallach reaction

A novel pathway towards trifluoromethylalcohols by an unexpected reaction of tert-butoxy-β-(trifluoromethyl)styrenes or corresponding trifluoromethylbenzyl ketones under the conditions of the Leuckart-Wallach reaction was elaborated.

Friedel-Crafts alkylations of arenes with mono- and bis(trifluoromethyl) oxiranes in superacid medium: Facile synthesis of α-(trifluoromethyl)- and α,α-bis(trifluoromethyl)-β-arylethanols

Triflic acid catalyzed Friedel-Crafts alkylation of aromatics with mono- and bis(trifluoromethyl)oxiranes through ring opening afforded α-(trifluoromethyl) and α,α-bis(trifluoromethyl)-β- phenylethanols in excellent yields. The regioselectivity of the oxirane ring opening and subsequent Friedel-Crafts alkylation have been found to depend on the electronic and steric effects of the substituents in the oxirane ring. DFT studies show that C2-O bond is longer than C1-O bond due to high electron-withdrawing effect of CF3 groups effecting C2-O cleavage resulting in a C2 electrophilic center promoting electrophilic substitution with the C2 center on aromatics. Georg Thieme Verlag Stuttgart.

Highly enantioselective transfer hydrogenation of fluoroalkyl ketones

(Chemical Equation Presented) The asymmetric transfer hydrogenation of fluoroalkyl ketones mediated by [Ru(η6-arene)((S,S)-R 2NSO2DPEN)] catalysts using HCO2H-Et 3N afforded the corresponding alcohols

Transfer hydrogenation of activated ketones using novel chiral Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes

A series of α-keto esters and α,α,α- trifluoromethyl ketones were reduced in high yields and excellent enantioselectivities under Ru-catalysed transfer hydrogenation using novel chiral N-arenesulfonyl-1,2-diphenylethylenediamine ligands.

Enantioselective Rhodium(I)-Catalyzed Hydrogenation of Trifluoromethyl Ketones

(Matrix Presented) The asymmetric hydrogenation of trifluoromethyl ketones to yield chiral α-trifluoromethyl alcohols with enantiomeric excesses up to 98% was achieved in the presence of chiral rhodium-(amidephosphine-phosphinite) complexes.