446-65-1

Basic information

• Product Name: 2,2,2-trifluoro-1-p-tolylethanol
• Synonyms: 2,2,2-trifluoro-1-p-tolylethanol
• CAS NO: 446-65-1
• Molecular Formula: C₉H₉F₃O
• Molecular Weight: 190.1623696
• Mol File: 446-65-1.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 230.8°Cat760mmHg
• Flash Point: 102.5°C
• Appearance: /
• Density: 1.241g/cm³
• Vapor Pressure: 0.036mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,2,2-trifluoro-1-p-tolylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-trifluoro-1-p-tolylethanol(446-65-1)
• EPA Substance Registry System: 2,2,2-trifluoro-1-p-tolylethanol(446-65-1)

Safety Data

• Hazardous Substances Data: 446-65-1(Hazardous Substances Data)

Usage

General Description

2,2,2-trifluoro-1-p-tolylethanol is a chemical compound with the molecular formula C8H9F3O. It is a halogenated alcohol that consists of a p-tolyl group attached to a trifluoroethyl group and a hydroxyl group. It is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. 2,2,2-trifluoro-1-p-tolylethanol has various applications in the pharmaceutical industry, especially in the development of new drugs or drug intermediates. It is also used as a reagent in organic synthesis and as a solvent in chemical reactions. Furthermore, it is often used as a chiral building block in the preparation of chiral ligands and catalysts for various reactions.

InChI:InChI=1/C9H9F3O/c1-6-2-4-7(5-3-6)8(13)9(10,11)12/h2-5,8,13H,1H3

Upstream product

• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 
• 75-63-8 Bromotrifluoromethane 
• 104-87-0 4-methyl-benzaldehyde 
• 445476-82-4 N,N-dimethyl-(1-phenyl-2,2,2-trifluoroethoxytrimethylsilyl)-amine 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 
• 589-18-4 4-Methylbenzyl alcohol 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 624-31-7 4-tolyl iodide 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 5720-05-8 4-methylphenylboronic acid 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 75-46-7 trifluoromethan 

Downstream Products

• 1682-48-0 2,2,2-Trifluor-1-p-tolyl-1-(4-chlor-phenyl)-aethan 
• 54743-54-3 di-p-methyl-α-trifluoromethylbenzyl ether 
• 708-65-6 1-chloro-1-(4-methylphenyl)-2,2,2-trifluoroethane 
• 128816-80-8 bis(2,2,2-trifluoroethyl)(p-methyl-α-trifluoromethylbenzyl) phosphate 
• 127936-14-5 Phenyl(p-methyl-α-trifluoromethylbenzyl) chlorophosphate 
• 1135312-20-7 2,2,2-trifluoro-1-(4'-methylphenyl)ethyl isobutyrate 
• 1135311-83-9 (S)-2,2,2-trifluoro-1-(4'-methylphenyl)ethyl isobutyrate 
• 72487-05-9 (R)-4-methyl-α-(trifluoromethyl)-benzenemethanol 
• 80446-60-2 (S)-4-methyl-α-(trifluoromethyl)-benzenemethanol 
• 70990-78-2 (E)-1-methyl-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene 
• 1422985-21-4 3-(1,1,1-trifluoro-3-nitro-2-p-tolylpropan-2-yl)-1H-indole 
• 1422984-78-8 C₁₀H₁₀F₃NO₃ 

Relevant articles and documents

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

One-Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α-Aryl-α-Trifluoromethyl Alcohols

A novel straightforward one-pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α-aryl-α-trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2-trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one-pot process: the iPrMgCl·LiCl-mediated iodine/magnesium-exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2-trifluoroethyl trifluoroacetate; and the reduction of in-situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α-aryl or α-heteroaryl-α-trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.

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.