N-benzyl-2-fluorobenzamide

Base Information

• Chemical Name: N-benzyl-2-fluorobenzamide
• CAS No.: 724-37-8
• Molecular Formula: C14H12FNO
• Molecular Weight: 229.254
• DSSTox Substance ID: DTXSID80350378
• Nikkaji Number: J1.846.935I
• Wikidata: Q82126288
• Mol file: 724-37-8.mol

Synonyms:N-benzyl-2-fluorobenzamide;724-37-8;Benzamide, 2-fluoro-N-(phenylmethyl)-;benzamide,2-fluoro-n-(phenylmethyl)-;SCHEMBL12181631;DTXSID80350378;STK415666;AKOS000576497;SR-01000361996;SR-01000361996-1;Z27749555

Chemical Property of N-benzyl-2-fluorobenzamide

Chemical Property:

• Melting Point: 39-40 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 392.6±35.0 °C(Predicted)
• PKA: 14.00±0.46(Predicted)
• PSA: 32.59000
• Density: 1.177±0.06 g/cm3(Predicted)
• LogP: 3.33050
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 229.090292168
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=O)C2=CC=CC=C2F

Technology Process of N-benzyl-2-fluorobenzamide

There total 13 articles about N-benzyl-2-fluorobenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

benzylamine (100-46-9) + 2-fluoro-benzoic acid 4-nitro-phenyl ester → 2-fluoro-N-(phenylmethyl)benzamide (724-37-8)

Guidance literature:

2-fluoro-benzoic acid 4-nitro-phenyl ester; With 1,3-dimethylimidazolim iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 0.333333h; Schlenk technique;

benzylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1055/s-0037-1610355

Reference yield: 86.0%

2-fluorobenzyl alcohol (446-51-5) + benzylamine (100-46-9) → 2-fluoro-N-(phenylmethyl)benzamide (724-37-8)

Guidance literature:

With [RuCl₂(cod)]_n; 1-ethyl-3-methyl-1H-benzo[d]imidazol-3-ium iodide; caesium carbonate; In toluene; for 36h; Inert atmosphere; Glovebox; Reflux; Schlenk technique; Green chemistry;

DOI:10.3390/molecules23102413

Reference yield: 85.0%

2-Fluorobenzaldehyde (446-52-6) + benzylamine (100-46-9) → 2-fluoro-N-(phenylmethyl)benzamide (724-37-8)

Guidance literature:

With tert.-butylhydroperoxide; copper(l) iodide; sodium hydride; 1,3-bis(mesityl)imidazolium chloride; In acetonitrile; at 90 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1055/a-1343-5203

upstream raw materials:

2-Fluorobenzoyl chloride

benzylamine

2-fluorobenzonitrile

N-benzyl-N-nitrosopivalamide

Downstream raw materials:

N-Benzyl-2-fluoro-benzimidoyl chloride

C₁₄H₁₂FNS

methyl N-[α-(trimethylsilyl)benzyl]benzimidate

dimethyl 2,5-diphenyl-1H-pyrrole-3,4-dicarboxylate

Refernces

• 1、 Singh, Ashmita,Narula, Anudeep Kumar. "Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines". supporting information. p. 718 - 722. Retrieved 2021/02/26.
• 2、 Bai, Ruopeng,Chatani, Naoto,Lan, Yu,Liu, Song,Nohira, Itsuki. "Nickel-Catalyzed C-F/N-H Annulation of Aromatic Amides with Alkynes: Activation of C-F Bonds under Mild Reaction Conditions". supporting information. p. 17306 - 17311. Retrieved 2020/11/13.