N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide

Base Information

• Chemical Name: N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide
• CAS No.: 175278-19-0
• Molecular Formula: C10H7 F3 N2 O2
• Molecular Weight: 244.173
• Hs Code.: 2926907090
• DSSTox Substance ID: DTXSID00371565
• Wikidata: Q82158930
• Mol file: 175278-19-0.mol

Synonyms:175278-19-0;N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide;4-Cyano-2-(trifluoromethoxy)acetanilide;N-(4-Cyano-2-(trifluoromethoxy)phenyl)acetamide;Acetamide, N-[4-cyano-2-(trifluoromethoxy)phenyl]-;4'-Cyano-2'-(trifluoromethoxy)acetanilide;Maybridge1_000083;MixCom1_000149;N1-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide;SCHEMBL4398648;DTXSID00371565;MFCD00204174;AKOS022181786;FS-1070;CS-0333838;FT-0629701;N-(4-cyano-2-trifluoromethoxyphenyl)-acetamide;A881591;4-cyano-2-(trifluoromethoxy)acetanilide, AldrichCPR

Chemical Property of N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide

Chemical Property:

• Vapor Pressure: 0.000223mmHg at 25°C
• Melting Point: 118 °C
• Refractive Index: 1.492
• Boiling Point: 325.9°C at 760 mmHg
• Flash Point: 150.9°C
• PSA: 62.12000
• Density: 1.38g/cm³
• LogP: 2.48828
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 244.04596196
• Heavy Atom Count: 17
• Complexity: 334

Purity/Quality:

98%min ^*data from raw suppliers

4-Cyano-2-(trifluoromethoxy)acetanilide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-36-22
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=C(C=C(C=C1)C#N)OC(F)(F)F

Technology Process of N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide

There total 4 articles about N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide 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: 63.0%

N-(4-cyanophenyl)-N-(trifluoromethoxy)acetamide → N-(4-cyano-2-(trifluoromethoxy)phenyl)acetamide (175278-19-0)

Guidance literature:

In nitromethane; at 120 ℃; for 48h; Inert atmosphere;

DOI:10.1002/anie.201409375

Reference yield:

4-nitrobenzonitrile (619-72-7) → N-(4-cyano-2-(trifluoromethoxy)phenyl)acetamide (175278-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrazine hydrate; 5% rhodium-on-charcoal / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

2: sodium hydrogencarbonate / diethyl ether / 0 °C / Inert atmosphere

3: caesium carbonate / chloroform / 23 h / 20 °C / Inert atmosphere

4: nitromethane / 48 h / 120 °C / Inert atmosphere

With 5% rhodium-on-charcoal; sodium hydrogencarbonate; caesium carbonate; hydrazine hydrate; In tetrahydrofuran; diethyl ether; nitromethane; chloroform;

DOI:10.1002/anie.201409375

Reference yield:

N-(4-cyanophenyl)acetohydroxamic acid (80584-65-2) → N-(4-cyano-2-(trifluoromethoxy)phenyl)acetamide (175278-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / chloroform / 23 h / 20 °C / Inert atmosphere

2: nitromethane / 48 h / 120 °C / Inert atmosphere

With caesium carbonate; In nitromethane; chloroform;

DOI:10.1002/anie.201409375

upstream raw materials:

4-nitrobenzonitrile

N-(4-cyanophenyl)acetohydroxamic acid

N-(4-cyanophenyl)hydroxylamine

Downstream raw materials:

N-[4-(N-hydroxycarbamimidoyl)-2-trifluoromethoxy-phenyl]-acetamide

Refernces

• 1、 Lee, Katarzyna N.,Lei, Zhen,Morales-Rivera, Cristian A.,Liu, Peng,Ngai, Ming-Yu. "Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration". . p. 5599 - 5605. Retrieved 2016/07/06.