2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-acrylamide

Base Information

• Chemical Name: 2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-acrylamide
• CAS No.: 90357-52-1
• Molecular Formula: C11H9F3N2O3
• Molecular Weight: 274.199
• European Community (EC) Number: 618-538-5
• DSSTox Substance ID: DTXSID601183982
• Mol file: 90357-52-1.mol

Synonyms:2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-acrylamide;SCHEMBL202765;DTXSID601183982;90357-52-1;2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-2-propenamide

Chemical Property of 2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-acrylamide

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 274.05652664
• Heavy Atom Count: 19
• Complexity: 390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F

Technology Process of 2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-acrylamide

There total 5 articles about 2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-acrylamide 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: 95.0%

4-nitro-3-(trifluoromethyl)benzeneamine (393-11-3) + Methacryloyl chloride (920-46-7,26937-45-1) → 2-methyl-N-<4-nitro-3-(trifluoromethyl)phenyl>-2-propenamide (90357-52-1)

Guidance literature:

In N,N-dimethyl acetamide; at 20 ℃; for 3h;

Reference yield: 88.0%

4-fluoro-1-nitro-2-trifluoromethyl-benzene (393-09-9) + Methacrylamide (79-39-0) → 2-methyl-N-<4-nitro-3-(trifluoromethyl)phenyl>-2-propenamide (90357-52-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.jorganchem.2010.10.051

Reference yield: 79.0%

4-nitro-3-(trifluoromethyl)benzeneamine (393-11-3) → 2-methyl-N-<4-nitro-3-(trifluoromethyl)phenyl>-2-propenamide (90357-52-1)

Guidance literature:

With zinc(II) chloride; In benzene; Heating;

DOI:10.1007/BF00758631

upstream raw materials:

4-nitro-3-(trifluoromethyl)benzeneamine

Methacryloyl chloride

poly(methacrylic acid)

4-fluoro-1-nitro-2-trifluoromethyl-benzene

Downstream raw materials:

3-methyl-5-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-carbothioic acid (4-nitro-3-trifluoromethyl-phenyl)-amide

Refernces

• 1、 Pertusati, Fabrizio,Ferla, Salvatore,Bassetto, Marcella,Brancale, Andrea,Khandil,Westwell, Andrew D.,McGuigan, Christopher. "A new series of bicalutamide, enzalutamide and enobosarm derivatives carrying pentafluorosulfanyl (SF5) and pentafluoroethyl (C2F5) substituents: Improved antiproliferative agents against prostate cancer". supporting information. p. 1 - 14. Retrieved 2019/07/10.
• 2、 -. "ANDROGEN RECEPTOR MODULATORS AND THEIR USE AS ANTI-CANCER AGENTS". Paragraph 0024; 0025. . Retrieved 2016/06/20.