671-01-2

Basic information

• Product Name: N-benzyl-3-fluorobenzamide
• Synonyms: N-benzyl-3-fluorobenzamide
• CAS NO: 671-01-2
• Molecular Formula: C₁₄H₁₂FNO
• Molecular Weight: 229
• Mol File: 671-01-2.mol

Chemical Properties

• Boiling Point: 392.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.177±0.06 g/cm3(Predicted)
• PKA: 14.37±0.46(Predicted)
• CAS DataBase Reference: N-benzyl-3-fluorobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-3-fluorobenzamide(671-01-2)
• EPA Substance Registry System: N-benzyl-3-fluorobenzamide(671-01-2)

Safety Data

• Hazardous Substances Data: 671-01-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-benzyl-3-fluorobenzamide is used as a key intermediate in the synthesis of various pharmaceuticals due to its potential to contribute to the development of new drugs. Its structural properties and reactivity allow for the creation of bioactive molecules with therapeutic applications.
Used in Organic Chemistry:
N-benzyl-3-fluorobenzamide serves as a valuable reagent in organic chemistry for the creation of functionalized aromatic compounds, which are essential in various chemical processes and product development.
Used in Agrochemical Industry:
N-benzyl-3-fluorobenzamide is utilized as a starting material in the synthesis of bioactive molecules for agrochemical applications, contributing to the development of effective crop protection agents and other agricultural products.
Used in Material Science:
In the field of material science, this compound is recognized for its potential as a key starting material for synthesizing a variety of materials with specific properties, enhancing the development of new materials with applications in different industries.

Upstream product

• 1711-07-5 3-fluorobenzoyl chloride 
• 100-46-9 benzylamine 
• 1380086-06-5 C₁₀H₁₃FO₂ 
• 456-47-3 3-fluoro-benzenemethanol 
• 403-54-3 m-Fluorobenzonitrile 
• 100-44-7 benzyl chloride 
• 122-04-3 4-nitro-benzoyl chloride 
• 100-20-9 terephthaloyl chloride 
• 140-11-4 Benzyl acetate 
• 538-86-3 benzyl methyl ether 
• 3173-56-6 benzyl isothiocyanate 
• 455-38-9 3-fluorobenzoic acid 

Downstream Products

• 185751-20-6 N-benzyl-3-fluorobenzimidoyl chloride 
• 185751-26-2 [(Diphenyl-phosphinoyl)-(3-fluoro-phenyl)-methyl]-[1-phenyl-meth-(E)-ylidene]-amine 

Relevant articles and documents

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands

The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.

Nickel-catalyzed reductive amidation of aryl-triazine ethers

The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.

Well-defined N-heterocyclic carbene/ruthenium complexes for the alcohol amidation with amines: The dual role of cesium carbonate and improved activities applying an added ligand

Dehydrogenative amide bond formation from alcohols and amines has been regarded as an atom-economic and sustainable process. Among various catalytic systems, N-heterocyclic carbene (NHC)-based Ru catalytic systems have attracted growing interest due to the outstanding properties of NHCs as ligands. Herein, an NHC/Ru complex (1) was prepared and its structure was further confirmed with X-ray crystallography. In the presence of Cs2CO3, two NHC/Ru-based catalytic systems were disclosed to be active for this amide synthesis. System A, which did not contain any added ligand, required a catalyst loading of 1.00 mol%. Interestingly, improved catalytic performance was realized by the addition of an NHC precursor (L). Optimization of the amounts of L and other conditions gave rise to system B, a much more potent system with the Ru loading as low as 0.25 mol%. Moreover, an NHC-Ru-carbonate complex 6 was identified from the refluxing toluene of 1 and Cs2CO3, and further investigations revealed that 6 was an important intermediate for this catalytic reaction. Based on the above results, we claimed that the role of Cs2CO3 was to facilitate the formation of key intermediate 6. On the other hand, it provided the optimized basicity for the selective amide formation.

Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene

Cyrene as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.

An efficient transformation of methyl ethers and nitriles to amides catalyzed by Iron(III) perchlorate hydrate

An efficient and inexpensive synthesis of N-substituted amides from the reaction of nitriles with methyl ethers catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter Reaction under solvent-free conditions. A range of methyl ethers (benzyl, sec-alkyl and tert-butyl ethers) were reacted with nitriles to provide the corresponding amides in high–excellent yields.

FeCl2·4H2O catalyzed ritter reaction with nitriles and halohydrocarbons

An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with various halohydrocarbons catalyzed by FeCl2·4H2O is described. FeCl2·4H2O economically efficiently catalyzed the Ritter reaction under solvent-free conditions. A range of halohydrocarbons (benzyl, tert-butyl and sec-alkyl halohydrocarbons) were coupled with nitriles to provide the corresponding amides in high to excellent yields.

Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis

We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.

Convenient synthesis of amides by Zn(ClO4)2·6H2O catalysed Ritter reaction with nitriles and halohydrocarbons

A convenient and high yielding procedure for the synthesis of amides by the Ritter reaction of nitriles and halohydrocarbons in the presence of Zn(ClO4)2·6H2O as a highly stable, effective and available catalyst is described.

Fe(ClO 4) 3 ·h 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles

An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO 4) 3 ·H 2 O is described. Fe(ClO 4) 3 ·H 2 O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.