82945-27-5

Basic information

• Product Name: 2-nitro-1-trifluoromethyl-1-phenyl-1-ethanol
• Synonyms: 2-nitro-1-trifluoromethyl-1-phenyl-1-ethanol
• CAS NO: 82945-27-5
• Molecular Weight: 235.163
• Mol File: 82945-27-5.mol

Chemical Properties

• CAS DataBase Reference: 2-nitro-1-trifluoromethyl-1-phenyl-1-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitro-1-trifluoromethyl-1-phenyl-1-ethanol(82945-27-5)
• EPA Substance Registry System: 2-nitro-1-trifluoromethyl-1-phenyl-1-ethanol(82945-27-5)

Safety Data

• Hazardous Substances Data: 82945-27-5(Hazardous Substances Data)

Upstream product

• 75-52-5 nitromethane 
• 434-45-7 2,2,2-Trifluoroacetophenone 

Relevant articles and documents

Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via CuI-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-CF3-β,β-Disubstituted Nitroalkenes

A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C-3 position of the pyrrolidine ring. The synthesis system, CuI/Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with β-CF3-β,β-disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee) and performs well for a broad scope of substrates under mild conditions.

Direct, catalytic enantioselective nitroaldol (Henry) reaction of trifluoromethyl ketones: an asymmetric entry to α-trifluoromethyl- substituted quaternary carbons

Herein we describe the first direct, catalytic enantioselective nitroaldol (Henry) reaction of simple α-trifluoromethyl ketones with nitromethane using a chiral monometallic lanthanum(III) triflate salt complex, namely [(Δ,S,S,S)-Binolam]3-La(O

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.

Deep eutectic solvent as solvent and catalyst: One-pot synthesis of 1,3-dinitropropanes: Via tandem Henry reaction/Michael addition

The Henry reaction was performed using microwave heating within the deep eutectic solvent (DES) choline chloride/urea (ChCl/urea) which acted as both the catalyst and solvent for the reaction. The optimisation of the conditions (temperature, heating mode,

Bioinspired Nitroalkylation for Selective Protein Modification and Peptide Stapling

Nitroalkanes react specifically with aldehydes, providing rapid, stable, and chemoselective protein bioconjugation. These nitroalkylated proteins mimic key post-translational modifications (PTMs) of proteins and can be used to understand the role of these

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

We have developed a catalytic system based on bianthrylbis(thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3:2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.

Access to Chiral GABA Analogues Bearing a Trifluoromethylated All-Carbon Quaternary Stereogenic Center through Water-Promoted Organocatalytic Michael Reactions

Water enables the highly challenging enantioselective Michael addition of sterically congested β-trifluoromethyl-β-aryl- or -alkyl-substituted nitroolefins with dithiomalonates. Under on-water conditions, the reaction rates were remarkably accelerated as

A asymmetric synthesis fluorine methyl chiral season carbon compound containing three method

The invention belongs to the technical field of an organic synthesis method, and particularly relates to a method for asymmetrically synthesizing a chiral quaternary carbon compound containing trifluoromethyl. The method comprises the following step: reacting trifluoromethyl nitroolefin with a 2-acetylaza aromatic compound to asymmetrically synthesize (R)-3- trifluoromethyl-3-nitryl methyl-1-(aza aromatic ring-2-yl)-butyl-1-acetone under the catalysis of bisoxazoline chiral ligand and a nickel catalyst in an organic solvent by adopting asymmetrically catalytic Michael addition reaction. The method is high in reaction yield and high in optical purity. The method disclosed by the invention can be used for a preparation tool for providing a trifluoromethyl quaternary carbon chiral compound.

The squaramide-catalyzed asymmetric Michael/cyclization tandem reaction for the synthesis of chiral trifluoromethylated hydroxyimino tetrahydrobenzofuranones

An enantioselective synthesis of trifluoromethylated hydroxyimino tetrahydrobenzofuranones has been developed. 1,3-Dicarbonyl carbocyclic compounds react with β-CF3-β-disubstituted nitroalkenes in the presence of a chiral squaramide catalyst, p

Enantioselective Michael Addition of Pyrazolin-5-ones to β-CF3-β-Disubstituted Nitroalkenes Catalyzed by Squaramide Organocatalyst

A highly enantioselective Michael addition of pyrazolin-5-ones with β-CF3-β-disubstituted nitroalkenes catalyzed by bifunctional squaramide has been developed. Various chiral β-CF3-β-5-hydroxy-pyrazolin-3-yl-disubstituted nitroalkane derivatives bearing all-carbon quaternary stereocenter were prepared in good yields (up to 88%) and excellent enantioselectivities (up to 97% ee).