351-28-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoroacetanilide is used as a reactant for the preparation of trifluoromethylaryl acetamides via Pd-catalyzed trifluoromethylation of aromatics C-H bond with Umemoto's reagent, which is directed by the acetamino group. This application is significant in the development of new pharmaceutical compounds with potential therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-Fluoroacetanilide is utilized as an essential building block for creating a range of complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of various compounds with diverse applications, including those in the pharmaceutical, agrochemical, and materials science industries.

InChI:InChI=1/C8H8FNO/c1-6(11)10-8-4-2-3-7(9)5-8/h2-5H,1H3,(H,10,11)

Upstream product

• 372-19-0 meta-fluoroaniline 
• 108-24-7 acetic anhydride 
• 91731-88-3 C₁₄H₁₁F₂N₃O 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 103-84-4 Acetanilid 
• 75-36-5 acetyl chloride 
• 3296-03-5 3-fluorophenylazide 
• 507-09-5 tiolacetic acid 
• 123-54-6 acetylacetone 
• 60-35-5 acetamide 
• 75-05-8 acetonitrile 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 141-78-6 ethyl acetate 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 500-41-4 3-fluoro-N-phenyl-aniline 
• 333-53-9 bis(3-fluorophenyl)amine 
• 347-71-7 N-(2-chloro-5-fluorophenyl)acetamide 
• 4053-51-4 2-acetylamino-1,4-benzoquinone 
• 227805-60-9 N,N-bis-(3-fluoro-phenyl)-acetamide 
• 82711-97-5 5-fluoro-2-nitrobenzenesulfonyl chloride 
• 118807-96-8 6-Fluoro-1H-benzoimidazole 3-oxide 
• 118807-64-0 2-cyano-6-fluoro-1H-benzimidazole 3-oxide 
• 118807-91-3 N-cyanomethyl-5-fluoro-2-nitroaniline 
• 1182601-90-6 butyl (E)-3-(2-acetamido-4-fluorophenyl)acrylate 
• 169214-32-8 C₈H₆⁽²⁾H₂FNO 
• 398-92-5 Ν-(2,4-dichloro-5-fluorophenyl)acetamide 
• 1331890-91-5 N-(3-fluoro-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide 
• 1308254-63-8 4-amino-2-fluoro-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds

Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Preparation method of acetamide compound

The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Magnetically recyclable silica-coated ferrite magnetite-K10montmorillonite nanocatalyst and its applications in O, N, and S-acylation reaction under solvent-free conditions

Novel silica-coated ferrite nanoparticles supported with montmorillonite (K10) have been prepared successfully by using a simple impregnation method. Further, these nanoparticles were characterized by using different analytical methods like FT-IR, PXRD, EDS, and FE-SEM techniques. In addition, these nanoparticles have been explored for their catalytic activity for the O, N, and S-acylation reactions under solvent-free conditions which gave moderate to excellent yields in a much shorter reaction time. Moreover, these nanoparticles could easily be separated out from the reaction medium after the reaction completion by using an external magnetic field and have been re-used for 10 cycles without any significant loss of the catalytic activity.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations

An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.

Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C-C bond cleavage

A catalyst-free, direct electrochemical synthesis of synthetically challenging medium-sized lactams through C-C bond cleavage has been developed. In contrast to previous typical amidyl radical cyclization, this electrosynthetic approach enabled step-economical ring expansion through a unique remote amidyl migration under mild, metal- and external-oxidant-free conditions in a simple undivided cell. The strategy features unparalleled broad substrate scope with all ring sizes of (hetero)aryl-fused 8-11-membered rings and hetero atom-tethered rings, high yields, and good functional group tolerance. Our experimental and computational findings provided strong support for a SET-based reaction manifold.