621-45-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-trifluoromethylphenyl)-2-propanol is used as a synthetic intermediate for the production of pharmaceuticals. Its unique structure allows it to be a valuable building block in the synthesis of various bioactive compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(3-trifluoromethylphenyl)-2-propanol serves as a synthetic intermediate for the creation of agrochemicals. Its incorporation into the chemical structure of these products can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Fine Chemicals Production:
1-(3-trifluoromethylphenyl)-2-propanol is also utilized in the production of other fine chemicals. Its presence in these compounds can improve their performance and expand their potential applications in various industries.
Used in Medicinal Chemistry and Drug Discovery:
1-(3-trifluoromethylphenyl)-2-propanol has potential applications in the field of medicinal chemistry and drug discovery. Its unique structure can be exploited to design and develop novel drugs with improved pharmacological properties, contributing to the advancement of medical treatments.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
1-(3-trifluoromethylphenyl)-2-propanol can be employed as a chiral auxiliary in asymmetric synthesis. Its presence can help achieve enantioselective reactions, leading to the production of optically active compounds with specific configurations. This is particularly important in the synthesis of chiral drugs, where the stereochemistry of the molecule plays a crucial role in its biological activity.

InChI:InChI=1/C10H11F3O/c1-7(14)5-8-3-2-4-9(6-8)10(11,12)13/h2-4,6-7,14H,5H2,1H3

Upstream product

• 713-71-3 2-<3-(trifluoromethyl)benzyl>oxirane 
• 15814-25-2 1-(meta-trifluoromethylphenyl)-1,2-propanediol 
• 21906-39-8 3-(trifluoromethyl)phenylacetone 
• 141-78-6 ethyl acetate 
• 2338-76-3 3-trifluoromethylphenylacetonitrile 

Downstream Products

• 135561-75-0 (S)-1-[(3′-trifluoromethyl)phenyl]-2-propanol 
• 135561-78-3 (R)-1-(3’-trifluoromethylphenyl)-2-propanol 
• 21906-39-8 3-(trifluoromethyl)phenylacetone 
• 1886-26-6 norfenfluramine 
• 1450816-97-3 1-(2-methoxypropyl)-3-(trifluoromethyl)benzene 
• 1450816-83-7 (E)-ethyl 3-(2-(2-methoxypropyl)-4-(trifluoromethyl)phenyl)acrylate 
• 135561-76-1 1-(3-(trifluoromethyl)phenyl)propan-2-yl 4-methylbenzenesulfonate 
• 1383841-49-3 1-(trifluoromethyl)-3-(2,3,3-trimethylbutyl)benzene 
• 1383841-39-1 1-(2-cyclohexylpropyl)-3-(trifluoromethyl)benzene 
• 213682-62-3 2-[(S)-1-Methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-isoindole-1,3-dione 
• 19036-73-8 (S)-norfenfluramine 

Relevant academic research and scientific papers

Group 6 Metal Carbonyl Complexes Supported by a Bidentate PN Ligand: Syntheses, Characterization, and Catalytic Hydrogenation Activity

We report on the preparation of a series of phosphorus-nitrogen donor ligand complexes [M(CO)4(PN)], where M = Cr, Mo, W and PN is 2-(diphenylphosphino)ethylamine. The organometallic compounds were readily obtained upon reacting the respective metal hexacarbonyls with equimolar amounts of the pertinent ligand in the presence of tetraethylammonium bromide. The PN-ligated metal carbonyls were fully characterized by standard spectroscopic techniques and X-ray crystallography. The ability of the title compounds to function as homogeneous hydrogenation catalysts was probed in the reduction of acetophenone and benzaldehyde derivatives to yield the corresponding alcohols. The reaction setup was easily assembled by simply combining the components in the autoclave on the bench outside an inert-gas-operated glovebox system.

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.

A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction

An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).

Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides

Enabled by nickel catalysis, a mild and general catalytic method for C-alkylation of nitroalkanes with unactivated alkyl iodides is described. Compatible with primary, secondary, and tertiary alkyl iodides; and tolerant of a wide range of functional groups, this method allows rapid access to diverse nitroalkanes.

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.).

Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes

A series of ketones and aldehydes are reduced in toluene under H2 in the presence of 5 mol % B(C6F5)3 and either cyclodextrin or molecular sieves affording a facile metal-free protocol for reduction to alcohols. Similar treatment of aryl ketones resulted in metal-free deoxygenation yielding aromatic hydrocarbons.

Enabling catalytic ketone hydrogenation by frustrated lewis pairs

Hydrogenation of alkyl and aryl ketones using H2 is catalytically achieved in 18 examples using 5 mol % B(C6F5)3 in an ethereal solvent. In these cases the borane and ether behave as a frustrated Lewis pair to activate H2 and effect the reduction.

Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst

Weak coordination is powerful! A PdII-catalyzed olefination of ortho-C-H bonds of arenes directed by weakly coordinating ethers is developed by using monoprotected amino acid (MPAA) ligands. This finding provides a method for chemically modifying ethers, which are abundant in natural products and drug molecules. HFIP=hexafluoroisopropanol. Copyright

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%.