143880-82-4

Basic information

• Product Name: (R)-phenyl[2-(trifluoromethyl)phenyl]methanol
• Synonyms: (R)-phenyl[2-(trifluoromethyl)phenyl]methanol
• CAS NO: 143880-82-4
• Molecular Weight: 252.236
• Mol File: 143880-82-4.mol

Chemical Properties

• CAS DataBase Reference: (R)-phenyl[2-(trifluoromethyl)phenyl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-phenyl[2-(trifluoromethyl)phenyl]methanol(143880-82-4)
• EPA Substance Registry System: (R)-phenyl[2-(trifluoromethyl)phenyl]methanol(143880-82-4)

Safety Data

• Hazardous Substances Data: 143880-82-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-phenyl[2-(trifluoromethyl)phenyl]methanol is used as an intermediate in the synthesis of pharmaceuticals. Its unique structure and chirality make it a valuable building block for creating new drugs with specific therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, (R)-phenyl[2-(trifluoromethyl)phenyl]methanol is utilized as an intermediate for the development of new compounds with pesticidal or herbicidal activities. Its specific configuration can contribute to the effectiveness and selectivity of these chemicals.
Used in Medicinal Chemistry Research:
As a chiral compound, (R)-phenyl[2-(trifluoromethyl)phenyl]methanol is important in drug discovery and development. It is used in research to understand the effects of stereochemistry on drug action, pharmacokinetics, and toxicity, which can lead to the design of more effective and safer medications.
Used in Material Science:
(R)-phenyl[2-(trifluoromethyl)phenyl]methanol's unique structure also makes it a potential candidate for applications in material science, where it could be used to develop new materials with specific properties, such as improved stability or reactivity.

Upstream product

• 447-61-0 2-Trifluoromethylbenzaldehyde 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 1078-58-6 diphenylzinc 
• 395-47-1 [2-(trifluoromethyl)phenyl]magnesium bromide 
• 727-98-0 phenyl[2-(trifluoromethyl)phenyl]methanol 
• 727-99-1 2-trifluoromethylbenzophenone 

Relevant articles and documents

Chiral electron-rich PNP ligand with a phospholane motif: Structural features and application in asymmetric hydrogenation

Despite the remarkable reactivity that was achieved by a series of transition-metal catalysts with a PNP type ligand, the electron-rich chiral PNP ligands have still been rarely reported because of the difficulties in synthesis and the nature of air-sensitivity. Herein, we report a novel chiral PNP ligand (Heng-PNP) with both a rigid backbone and a bulky tert-butyl group on the phospholane motif. We successfully obtained its divalent iron complex. The chiral environment of its Ir(III) complex was also discussed with quadrant analysis. This tridentate ligand was applied in iridium-catalyzed asymmetric hydrogenation of challenging diaryl ketones: up to 98% ee and 500 TON are achieved. Computational study showed that the twist of conjugate aryl group in the substrate (induced by the special chiral pocket of Ir/Heng-PNP complex) leads to the energy difference in the enantiodetermining step.

Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo- and Enantio-Selective Aryl Transfer Reagents

An enantioselective aryl transfer is promoted using chiral tricoordinated lithium amido aryl zincates that are easily accessible reagents and whose chiral appendage is simply recovered for reuse. The arylation reaction is run in good yields (60 % average on twenty substrates) and high enantiomeric excesses (95 % ee average). This occurs whatever the ortho, meta, or para substituent borne by the substrate and a complete chemoselectivity is observed with respect to the aldehyde function. Sensitive groups such as nitriles, esters, ketones, and enolisable substrates resist to the action of the ate reagent, warranting a large scope to this methodology.

Catalytic enantioselective aryl transfer to aldehydes using chiral 2,2'-bispyrrolidine-based salan ligands

Chiral C2-symmetric diamines have emerged as versatile auxiliaries or ligands in numerous asymmetric transformations. Chiral 2,2'-bispyrrolidine-based salan ligands were prepared and applied to the asymmetric aryl transfer to aldehydes with arylboronic acids as the source of transferable aryl groups. The corresponding diarylmethanols were obtained in high yields with moderate to good enantioselectivitives of up to 83% ee.

Evaluation of enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl) methanol for catalytic asymmetric addition of organozinc reagents to aldehydes

(Chemical Equation Presented) A facile and practical approach to preparation of enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)-methanol was developed from cheap and easily available L-(+)-methionine. Synthetic highlights include the three-step, one-pot construction of the chiral azetidine ring and the development of an improved one-step procedure for the synthesis of the key intermediate L-2-amino-4-bromobutanoic acid. Enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol was evaluated for catalytic asymmetric addition of organozinc reagents to aldehydes. The asymmetric ethylation, methylation, arylation, and alkynylation of aldehydes achieved enantioselectivity of up to 98.4%, 94.1%, 99.0%, and 84,6% ee, respectively, in the presence of a catalytic amount of chiral N-(ferrocenylmethyl)azetidin-2- yl(diphenyl)methanol. Our results demonstrated further that the four-membered heterocycle-based backbone was a good potential chiral unit for the catalytic asymmetric induction reaction, and the hindrance of the bulky ferrocenyl group, compared to a phenyl group, played an important role in the enantioselectivities. A possible transition for the catalytic asymmetric addition has been proposed on the basis of the crystal structure of the chiral ligand 3b including two HOAc molecules and previous studies.

Catalytic asymmetric aryl transfer: highly enantioselective preparation of (R)- and (S)-diarylmethanols catalyzed by the same chiral ferrocenyl aziridino alcohol

Highly enantioselective arylations of arylaldehydes using arylboronic acids as aryl resource were realized in the presence of a catalytic amount of (2S)-1-ferrocenylmethylaziridin-2-yl(diphenyl)methanol. In addition, the R or S enantiomers of a series of given diarylmethanols can be easily obtained in high yields with excellent enantioselectivities simply by the reverse combinations of both reaction partners. A possible transition state for the catalytic asymmetric addition has been proposed on the basis of previous studies.

Method for Asymmetric Hydrosilylation of Ketones

Method of asymmetrically hydrosilylating substrates using catalysts having a ligand of the compound of the formula (I) wherein R is optionally substituted alkyl, cycloalkyl, aryl or heteroaryl;R′ is hydrogen, optionally substituted lower alkyl; andR″ is hydrogen, halogen, optionally substituted alkyl, hydroxy, amino (e.g., primary, secondary or tertiary), alkenyl; or an enantiomer thereof; or an enantiomeric mixture thereof with a transition metal. Particularly suitable reactions include the asymmetric hydrosilylation of ketones.

New enantiopure N-ferrocenylmethyl azetidin-2-yl(diphenyl)methanol and its application in catalytic asymmetric ethylation and arylation of arylaldehydes

A novel, facile and practical approach to preparation of new enantiopure N-ferrocenylmethyl azetidin-2-yl(diphenyl)methanol has been developed. In the presence of a catalytic amount of the chiral N-ferrocenylmethyl azetidin-2-yl(diphenyl)methanol, the enantioselective ethylation and arylation of arylaldehydes afforded addition products with enantioselectivities of up to 98.4% ee and 95.7% ee, respectively. Georg Thieme Verlag Stuttgart.

Determination of the Enantiomeric Excesses of Chiral Acids by 19F NMR Studies of their Esters deriving from (R)-(+)-2-(Trifluoromethyl)benzhydrol

15-Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent.With respect to the carboxy group, the stereogenic centre is in the β-position in the case of the acids 5a-10a and 12a-16a, and in the α position in the case of the acids 17a-20a.The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of 19F NMR.These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.

Preparative syntheses of optically pure ortho-substituted benzhydrols by asymmetric reductions of the corresponding benzophenones

Lithium aluminium hydride previously treated with 2.5 equivalents of (S)-(+) or (R)-(-)-2-(2-iso-indolinyl)butan-1-ol 3 (readily available reagents) reduced the five ortho-substituted benzophenones 4-6, 8 and 10 into the corresponding optically active benzhydrols with nearly 100% enantiomeric excesses. Other examples of asymmetric reductions of prochiral benzophenones are given.