371-96-0

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-3,3,3-trifluoro-1-nitro-prop-1-ene is used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a key component in the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
(Z)-3,3,3-trifluoro-1-nitro-prop-1-ene is also used as an intermediate in the synthesis of agrochemicals. Its properties allow for the creation of novel compounds with enhanced pesticidal or herbicidal activities, contributing to more effective crop protection solutions.
Used in Organic Synthesis:
As a versatile building block, (Z)-3,3,3-trifluoro-1-nitro-prop-1-ene is used in organic synthesis for the preparation of complex organic molecules. Its trifluoro substituents and nitro group provide unique reactivity and opportunities for further derivatization, facilitating the synthesis of a wide range of chemical products.
Used in Chemical Research:
(Z)-3,3,3-trifluoro-1-nitro-prop-1-ene serves as an important reagent in chemical research, enabling scientists to explore new reaction pathways and develop innovative synthetic methods. Its unique properties make it a valuable tool for studying the reactivity and stability of α,β-unsaturated nitro compounds and their derivatives.

InChI:InChI=1/C3H2F3NO2/c4-3(5,6)1-2-7(8)9/h1-2H/b2-1-

Upstream product

• 453-35-0 1,1,1-trifluoro-3-nitro-2-propanol 
• 6214-30-8 β-carboxynitroethylene 
• 75-52-5 nitromethane 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 

Downstream Products

• 37467-91-7 C₇H₄⁽²⁾H₄F₃NO₂ 
• 890095-37-1 3-nitro-2-(trifluoromethyl)-2H-chromene 
• 928779-90-2 3-nitro-2-(3-trifluoromethylphenyl)amino-1,1,1-trifluoropropane 
• 1033425-32-9 1,1,1-trifluoro-3-nitro-N-[1-(4,6-dimethyl-2-hydroxyphenyl)ethylidene]propan-2-amine 
• 1033425-24-9 4-methyl-3-nitro-2-(trifluoromethyl)-2H-chromene 
• 1033425-33-0 (E)-1,1,1-trifluoro-3-nitro-N-[1-(2-hydroxyphenyl)ethylidene]propan-2-amine 
• 616864-67-6 (R)-3-Phenyl-2-((R)-2,2,2-trifluoro-1-nitromethyl-ethylamino)-propionic acid methyl ester 

Relevant academic research and scientific papers

3,3,3-Trifluoro-1-nitropropene as a Novel Trifluoromethyl-Containing Building Block

Additions of various carbanion nucleophiles to 3,3,3-trifluoro-1-nitropropene (1) proceeded regiospecifically at the C-2 position of 1 to give the corresponding adducts.The nitro group of the adducts, derived from the reactions with acetylacetone and ethyl acetoacetate, was reduced to the corresponding amines, which were cyclized in situ to the 3-(trifluoromethyl)pyrrole derivatives.

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.

Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones

Reactions of 3,3,3-trihalogen-1-nitropropenes with N-alkyl-α-amino acids (sarcosine, proline) and isatins proceed regio- and diastereoselectively to give a wide range of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate stabilised azomethine ylide at the double bond of the nitroalkenes.

Stereocontrolled Synthesis of ψ[CH(CF3)NH]Gly-Peptides

(Matrix presented). A novel class of peptidomimetics having a stereogenic [CH(CF3)NH] replacement for a [CONH] peptide bond has been synthesized. The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

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.

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

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

Investigation of reaction between 2-diazo-3-nitro-1,1,1 -trifluoropropane and ethyl 3-morpholinocrotonate. The problem of existence of trifluoromethylnitromethylcarbene anion

Reaction of 2-diazo-3-nitro-l,l,l-trifluoropropane with ethyl 3-morpholinocrotonate results in ethyl 2-methyl-2-morpholino-3-nitro-4-trifluoromethylcyclobutanoate. Acidic hydrolysis of the latter compound affords ethyl 2-(2-nitroethyl-l-trifluoroethyl)butanoate-3 occuring as a mixture of enol and two diastereomeric ketone forms. The presumed reaction mechanism includes formation in the presence of a catalytic quantity of base of trifluoromethylnitromethylcarbene anion which reacts by two routes: insertion into the olefin C-H bond of enamine with subsequent cyclization of the intermediate, and carbene-olefin isomerization yielding 3-nitro-l,l,l-trifluoro-2-propene which adds to enamine by Michael reaction.