32471-55-9

Usage

Synthesis Reference(s)

Tetrahedron, 31, p. 391, 1975 DOI: 10.1016/0040-4020(75)80050-0

InChI:InChI=1/C8H7F2NO2/c1-8(9,10)6-2-4-7(5-3-6)11(12)13/h2-5H,1H3

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 52376-81-5 p-Nitroacetophenone semicarbazone 
• 28153-22-2 1-(4-nitrophenyl)ethanone hydrazone 
• 1448631-99-9 4-nitrophenyl(anisyl)iodonium triflate 
• 115134-88-8 (1,1-difluoroethyl)trimethylsilane 
• 1146127-11-8 (4-nitrophenyl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate 
• 133932-54-4 p-nitroacetophenone methylhydrazone 
• 133932-41-9 1-(1,1-Difluoro-2-iodo-ethyl)-4-nitro-benzene 

Downstream Products

• 64833-17-6 1-Aethoxy-2-p-nitrophenylaethylen 

Relevant academic research and scientific papers

Scalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF4)

A general approach to fluorinated (hetero)aromatic derivatives is elaborated. The key reaction is a deoxofluorination of substituted acetophenones with sulfur tetrafluoride (SF4). In contrast to previous deoxofluorination methods, this transformation is fast, scalable (up to 70 g), and high-yielding. More than 100 novel or previously hardly accessible fluorinated heterocycles, interesting for medicinal chemistry and agrochemistry, were synthesized.

Copper-Mediated Aromatic 1,1-Difluoroethylation with (1,1-Difluoroethyl)trimethylsilane (TMSCF2CH3)

A new method for the formation of 1,1-difluoroethyl copper species (“CuCF2CH3”) with 1,1-difluoroethylsilane (TMSCF2CH3) has been developed. The “CuCF2CH3” species can be applied to the efficient 1,1-difluoroethylation of diaryliodonium salts under mild conditions, affording (1,1-difluoroethyl)arenes in good to excellent yields. This convenient procedure tolerates a wide range of functional groups and thus serves as a practical synthetic tool for the introduction of CF2CH3 group(s) into complex molecules.

Fluorinating cleavage of solid phase linkers for combinatorial synthesis

(Figure Presented) Multitasking: A new preparative route to fluorine-containing compounds combines the advantages ofsolid-phase synthesis with the incorporation off luorine at the end ofthe synthetic route. A sulfur linker enables simultaneous fluorination of the target structures in the cleavage step. As it is stable under different reaction conditions, the linker has potential in the combinatorial synthesis off luorinated drug structures.

Process for the production of fluorinated organic compounds and fluorinating agents

A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.

Conversion of the Carbonyl Group to CF2 Using IF

A novel method for the transformation of CO -> CF2 is described.The easily made hydrazone derivatives of the carbonyl moiety are reacted under mild conditions with IF prepared directly from the corresponding elements.Various hydrazones have been examined and compared with each other.Unsubstituted ones are usually the most suitable although they are not always easy to purify and store.N-Methyl- and N,N-dimethylhydrazones also give quite satisfactory results.The more easily made dinitrophenyl hydrazones (DNPs), semicarbazones, and tosylhydrazones also react, but the yields of the desired CF2 compounds are usually lower.Oximes could also be successfully reacted.The two main byproducts of the reaction are the parent carbonyl compounds, which can be recycled, and the α-iododifluoro derivatives.The latter upon treatment with LiAlH4 or Bu3SnH were reduced to the desired product, thus increasing the overall yields.