455-37-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluorobenzamide is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
3-Fluorobenzamide is used as a reagent in the synthesis of N-(3-fluorobenzoyl)-N′,N′′-bis(4-methylphenyl)phosphoric triamide. 3-FLUOROBENZAMIDE has potential applications in the development of new materials and chemicals with specific properties.

InChI:InChI=1/C7H6FNO/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 1711-07-5 3-fluorobenzoyl chloride 
• 456-47-3 3-fluoro-benzenemethanol 
• 456-48-4 3-Fluorobenzaldehyde 
• 451-02-5 ethyl 3-fluorobenzoate 
• 75-05-8 acetonitrile 
• 100-82-3 (3-fluorophenyl)methanamine 
• 350-51-6 3-fluorostyrene 
• 53631-18-8 2-bromo-1-(3-fluorophenyl)ethanone 
• 458-02-6 3-fluorobenzaldehyde oxime 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 201230-82-2 carbon monoxide 
• 32222-47-2 2-(3-fluorophenyl)-2-hydroxyacetic acid 
• 331-25-9 (3-fluorophenyl)acetic acid 
• 403-54-3 m-Fluorobenzonitrile 

Downstream Products

• 52059-64-0 HT₁₀₇₁ 
• 455-38-9 3-fluorobenzoic acid 
• 908373-50-2 [2-(3-Fluoro-phenyl)-5-methyl-oxazol-4-yl]-acetic acid methyl ester 
• 403509-10-4 N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dichloropropyl]-3-fluorobenzamide 
• 455-68-5 methyl 3-fluorobenzoate 
• 1092101-19-3 (4-benzylsulfanyl-pyrimidin-5-yl)-methyl-amine 
• 1092101-28-4 6-benzylsulfanyl-8-(3-fluoro-phenyl)-7-methyl-7H-purine 
• 72755-13-6 (3-fluoro-phenyl)-carbamic acid methyl ester 
• 1415749-93-7 N,N,N',N'-tetrabenzyl-N''-(3-fluorobenzoyl)phosphoric triamide 
• 777-01-5 N-<3-Fluor-benzoyl>-amidophosphorsaeure-dichlorid 
• 1629-09-0 3-fluoro-N-phenylbenzamide 
• 1978-87-6 3-fluoro-N-(4-chlorophenyl)benzamide 

Relevant academic research and scientific papers

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Mechanochemical Synthesis of Primary Amides

Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

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.

Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation

A simple and efficient system for the hydration and α-deuteration of nitriles to form amides, α-deuterated nitriles, and α-deuterated amides catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert-butanol to toluene and using D2O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D2O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations.

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3surrogates

A simple, efficient and phosphine free protocol for carbonylative synthesis of primary aromatic amides under polystyrene supported palladium (Pd?PS) nanoparticle (NP) catalyzed conditions has been demonstrated. Herein, instead of using two toxic and difficult to handle gases simultaneously, we have employed the solid, economical, bench stable oxalic acid as the CO source and ammonium carbamate as the NH3source in a single pot reaction. For the first time, we have applied two non-gaseous surrogates simultaneously under heterogeneous catalyst (Pd?PS) conditions for the synthesis of primary amides using an easy to handle double-vial (DV) system. The developed strategy showed a good functional group tolerance towards a wide range of aryl iodides and afforded primary aromatic amides in good yields. The Pd?PS catalyst was easy to separate and can be recycled up to four consecutive runs with small loss in catalytic activity. We have successfully extended the scope of the methodology to the synthesis of isoindole-1,3-diones from 1,2-dihalobenzene, 2-halobenzoates and 2-halobenzoic acid following double and single carbonylative cyclization approaches.

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.

Arene-ruthenium(II)-phosphine complexes: Green catalysts for hydration of nitriles under mild conditions

Three new arene-ruthenium(II) complexes were prepared by treating [{RuCl(μ-Cl)(η6-arene)}2] (η6-arene = p-cymene) dimer with tri(2-furyl)phosphine (PFu3) and 1,3,5-triaza-7-phosphaadamantane (PTA), respectively to obtain [RuCl2(η6-arene)PFu3] [Ru]-1, [RuCl(η6-arene)(PFu3)(PTA)]BF4 [Ru]-2 and [RuCl(η6-arene)(PFu3)2]BF4 [Ru]-3. All the complexes were structurally identified using analytical and spectroscopic methods including single-crystal X-ray studies. The effectiveness of resulting complexes as potential homogeneous catalysts for selective hydration of different nitriles into corresponding amides in aqueous medium and air atmosphere was explored. There was a remarkable difference in catalytic activity of the catalysts depending on the nature and number of phosphorus-donor ligands and sites available for catalysis. Experimental studies performed using structural analogues of efficient catalyst concluded a structural-activity relationship for the higher catalytic activity of [Ru]-1, being able to convert huge variety of aromatic, heteroaromatic and aliphatic nitriles. The use of eco-friendly water as a solvent, open atmosphere and avoidance of any organic solvent during the catalytic reactions prove the reported process to be truly green and sustainable.

Aerobic oxidation of primary benzylic amines to amides and nitriles catalyzed by ruthenium carbonyl clusters carrying N,O-bidentate ligands

Four trinuclear ruthenium carbonyl clusters, (6-BrPyCHRO)2Ru3(CO)8 (R = 4-OCH3C6H4, 1a; R = 4-BrC6H4, 1b) and (2-OC6H4-HCN-C6H4R)2Ru3(CO)8 (R = 4-OCH3, 2a; R = 4-Br, 2b), were synthesized from the reactions of Ru3(CO)12 with the corresponding N,O-bidentate ligands (two pyridyl alcohols and two Schiff bases) respectively in a ratio of 1:2. Three new complexes 1b, 2a and 2b have been fully characterized by elemental analysis, FT-IR, NMR and X-ray crystallography. The catalytic activity of these ruthenium complexes for the aerobic oxidation of primary benzylic amines to amides and nitriles in the presence of t-BuOK was investigated, of which the Schiff base complex 2a was found to exhibit the highest activity.

One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).