N-(3-fluorophenyl)-2-phenylacetamide

Base Information

• Chemical Name: N-(3-fluorophenyl)-2-phenylacetamide
• CAS No.: 5215-27-0
• Molecular Formula: C14H12FNO
• Molecular Weight: 229.254
• DSSTox Substance ID: DTXSID40358916
• Nikkaji Number: J1.586.204A
• Wikidata: Q82139833
• Mol file: 5215-27-0.mol

Synonyms:N-(3-fluorophenyl)-2-phenylacetamide;5215-27-0;benzeneacetamide,n-(3-fluorophenyl)-;DTXSID40358916;STK412764;AKOS001215684;Z28143200

Chemical Property of N-(3-fluorophenyl)-2-phenylacetamide

Chemical Property:

• XLogP3: 3
• 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)CC(=O)NC2=CC(=CC=C2)F

Technology Process of N-(3-fluorophenyl)-2-phenylacetamide

There total 6 articles about N-(3-fluorophenyl)-2-phenylacetamide 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: 85.0%

tert-butyl N-(3-fluorophenyl)-N-(phenylethynyl)carbamate → N-(3-fluorophenyl)-2-phenylacetamide (5215-27-0)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2016.03.052

Reference yield: 54.0%

meta-fluoroaniline (372-19-0) + carbon monoxide (201230-82-2) + toluene (108-88-3,15644-74-3,16713-13-6) → N-(3-fluorophenyl)-2-phenylacetamide (5215-27-0)

Guidance literature:

With di-tert-butyl peroxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium dichloride; at 125 ℃; for 24h; under 38002.6 Torr; Autoclave;

DOI:10.1039/c3cc47015f

Reference yield:

t-butyl<3-(trifluoromethyl)phenyl>-carbamate (109134-07-8) + 1-Bromo-2-phenylacetylene (932-87-6) → N-(3-fluorophenyl)-2-phenylacetamide (5215-27-0) + N-(3-chlorophenyl)-2-phenylacetamide (18109-43-8) + 3-(benzo[d][1,3]dioxol-5-yl)-5-phenyl-5-(p-tolylthio)oxazolidine-2,4-dione + 2-phenyl-N-(3-(trifluoromethyl)phenyl)acetamide (1939-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(ll) sulfate pentahydrate; 1,10-Phenanthroline; potassium phosphate / toluene / 18 h / 85 °C / Sealed tube

2: trifluoroacetic acid; water / dichloromethane / 3 h / 20 °C

With potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; water; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2016.03.052

upstream raw materials:

meta-fluoroaniline

phenylacetyl chloride

carbon monoxide

toluene

Refernces

• 1、 Liu, Huizhen,Laurenczy, Gabor,Yan, Ning,Dyson, Paul J.. "Amide bond formation via C(sp3)-H bond functionalization and CO insertion". supporting information. p. 341 - 343. Retrieved 2014/01/06.