453-35-0

Usage

Uses

Used in Pharmaceutical Synthesis:
1,1,1-Trifluoro-3-nitropropan-2-ol is utilized as a key intermediate in the production of pharmaceuticals, contributing to the development of new medications and therapeutic agents. Its unique chemical structure allows it to participate in various chemical reactions, facilitating the synthesis of a wide array of drug compounds.
Used in Agricultural Chemical Production:
1,1,1-TRIFLUORO-3-NITROPROPAN-2-OL also plays a significant role in the synthesis of agricultural chemicals, such as pesticides and herbicides. Its application in this industry aids in the development of more effective and targeted agrochemicals to enhance crop protection and yield.
Used as a Solvent in Chemical Reactions:
1,1,1-Trifluoro-3-nitropropan-2-ol is employed as a solvent in numerous chemical processes, providing a medium for reactions to occur. Its properties enable it to dissolve a variety of substances and facilitate the progress of chemical reactions, making it a valuable component in the synthesis of numerous organic compounds.
Used in Organic Compound Synthesis:
Beyond its applications in pharmaceuticals and agricultural chemicals, 1,1,1-trifluoro-3-nitropropan-2-ol is also used in the synthesis of other organic compounds. Its versatility as a chemical intermediate allows it to be incorporated into the production of a diverse range of organic substances, expanding its utility across various industries.

InChI:InChI=1/C3H4F3NO3/c4-3(5,6)2(8)1-7(9)10/h2,8H,1H2

Upstream product

• 75-52-5 nitromethane 
• 461-24-5 1,1,1-trifluoroethyl ethyl ether 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 112091-98-2 1,1,1-trifluoro-2-diazo-3-nitropropane 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 

Downstream Products

• 371-96-0 (E)-3,3,3-trifluoro-1-nitroprop-1-ene 
• 431-38-9 3-amino-1,1,1-trifluoropropan-2-ol 

Relevant academic research and scientific papers

Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: Synthesis of trihalomethylated spiroindenepyrroli(zi)dines

Reactions of (E)-3,3,3-trihalogeno-1-nitropropenes with stabilised azomethine ylides derived from ninhydrin and indenoquinoxalinones on the one hand, and sarcosine and proline on the other, proceed regio- and diastereoselectively to give a number of trihalomethylated spiroindenepyrrolidines and spiroindenepyrrolizidines in good yields.

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

6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE COMPOUNDS FOR THE TREATMENT OF INFECTIOUS DISEASES

The present invention relates to compounds of the formula (I) or pharmaceutically acceptable salts, enantiomer or diastereomer thereof, wherein R1 to R4 are as described above. The compounds may be useful for the treatment or prophylaxis of hepatitis B virus infection.

1-Bromo-3,3,3-trifluoro-1-nitropropene: Synthesis and reaction with phenyl azide

An improved procedure was developed for the synthesis of 3,3,3-trifluoro-1-nitropropene, and a new representative of gem-bromonitroalkenes, 1-bromo-3,3,3-trifluoro-1-nitropropene, was synthesized therefrom. Its reaction with phenyl azide gave a mixture of two regioisomeric 1,2,3-triazoles, from which pure 5-nitro-1-phenyl-4-(trifluoromethyl)-1H-1,2,3-triazole was isolated.

The asymmetric Friedel-Crafts reaction of indoles with fluoroalkylated nitroalkenes catalyzed by chiral phosphoric acid

The enantioselective Friedel-Crafts fluoroalkylation of indoles with fluoroalkylated nitroalkenes, catalyzed by chiral phosphoric acid is described. The regioselectivity of fluoroalkylated nitroalkenes is a problem worth discussing, and it was found that the carbon atom adjacent to the fluoroalkyl group is more reactive than that adjacent to NO2 group.

Ψ[CH(CF3)NH]Gly-peptides: Synthesis and conformation analysis

Ψ[CH(CF3)NH]Gly peptides, a conceptually new class of peptidomimetics having a stereogenic trifluoroethylamine group as a natural peptide-bond surrogate, have been synthesized by stereoselective addition of α-amino acid esters to trans-3,3,3-tr

Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease

A series of trifluoromethyl ketones as SARS-CoV 3CL protease inhibitors was developed. The inhibitors were synthesized in four steps from commercially available compounds. Three different amino acids were explored in the P1-position and in the P2-P4 positions varying amino acids and long alkyl chain were incorporated. All inhibitors were evaluated in an in vitro assay using purified enzyme and fluorogenic substrate peptide. One of the inhibitors showed a time-dependent inhibition, with a Ki value of 0.3 μM after 4 h incubation.

Synthesis of Ψ[CH(RF)NH]Gly-peptides: The dramatic effect of a single fluorine atom on the diastereocontrol of the key aza-Michael reaction

We describe in full-detail the synthesis of new ψ[CH(RF)NH]-peptidomimetics, having different fluoroalkyl groups RF, as peptide bond surrogates. A key step in the synthesis is a stereoselective aza-Michael addition of chiral α-amino acid esters to β-fluoroalkyl-α-nitroethenes. The diastereoselection of the process was influenced by the electronegativity, rather than by the steric bulk, of the fluorinated residue RF in the β-position of the nitroalkene acceptors. Replacement of a single F atom of RF by a hydrogen or methyl group brings about a dramatic drop of stereocontrol, whereas Br, Cl and CF3, albeit bulkier than F, provide inferior results in terms of stereocontrol. A mechanistic hypothesis is provided.

The influence of fluoroalkyl-group electronegativity on stereocontrol in the synthesis of ψ[CH(RF)NH]Gly peptides

New peptidomimetics featuring CH(RF)NH units, having different degree of fluorination, as peptide-bond surrogates have been synthesized. The key step in the synthesis consists of a stereo-selective aza-Michael addition of chiral α-amino acid es

New functionalized, differently fluorinated building-blocks via Michael addition to γ-fluoro-α-nitroalkenes

The Michael addition of ketone-derived enamines, metalated methylene active compounds and N-methyl pyrroles to γ-fluoro-α-nitroalkenes provided in moderate to good isolated yields the corresponding β-fluoroalkyl nitro compounds, which represent new intere