N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

Base Information

• Chemical Name: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide
• CAS No.: 90357-51-0
• Molecular Formula: C12H9F3N2O2
• Molecular Weight: 270.211
• Hs Code.: 29269090
• European Community (EC) Number: 618-536-4
• DSSTox Substance ID: DTXSID60436169
• Nikkaji Number: J2.054.393K
• Mol file: 90357-51-0.mol

Synonyms:90357-51-0;N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide;N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide epoxide;N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide;N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide;Oxiranecarboxamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-;4-Cyano-N-(2,3-epoxy-2-methylpropionyl)-3-trifluoromethylaniline;MFCD08460201;N-[4-Cyano-3-(Trifluoromethyl)Phenyl]-2-Methyl-2-Oxirane Carboxamide;N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-oxirane-2-carboxamide;N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide;Oxiranecarboxamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl- (9CI);2-Methyloxirane-2-carboxylic acid N-(4-cyano-3-trifluoromethylphenyl)amide;Oxiranecarboxamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-, (+/-)-;SCHEMBL202481;DTXSID60436169;AKOS015900542;AC-1069;CS-T-13775;DS-3154;SY033473;AM20041370;C3607;CS-0153887;Q-100884;N-[4-cyano-3-trifluoromethylphenyl]-2-methyloxiranecaboxamide;Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxirane carboxamide;N-[3-(Trifluoromethyl)-4-cyanophenyl]-2-methyloxirane-2-carboxamide;1,2-Epoxy-2-methyl-N-[4-cyano-3-(trifluoromethyl)-phenyl]propionamide;2-Methyl-oxirane-2-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide;N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarbox-amide;N-(4-cyano-3-(trifluoromethyl)phenyl)methacrylamide;N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

Chemical Property of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 151-152 °C
• Refractive Index: 1.526
• Boiling Point: 436.366 °C at 760 mmHg
• PKA: 12.08±0.70(Predicted)
• Flash Point: 217.707 °C
• PSA: 65.42000
• Density: 1.42 g/cm³
• LogP: 2.37748
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 270.06161202
• Heavy Atom Count: 19
• Complexity: 428

Purity/Quality:

99% ^*data from raw suppliers

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CO1)C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F
• Uses: N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide, is an intermediate in synthesis of more complex pharmaceutical compounds. It is used in the synthesis of potential impurities of Bicalutamide (B382000), which is an oral nonsteroidal, anti-androgen drug used for prostate cancer.

Technology Process of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

There total 11 articles about N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide 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: 100.0%

monoperoxyphthalic acid (2311-91-3) + N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide (90357-53-2) → N-[4-cyano-3-(trifluoromethyl)-phenyl]-2,3-dihydroxy-2-methyl-propionamide (316373-92-9) + N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide (90357-51-0)

Guidance literature:

In ethyl acetate; at 20 - 55 ℃; Product distribution / selectivity;

Reference yield: 100.0%

C12H10ClF3N2O2 (627484-44-0) → N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide (90357-51-0)

Guidance literature:

In dimethyl sulfoxide; at 30 ℃; pH=9; pH-value; Temperature; Kinetics; aq. buffer; Alkaline conditions;

DOI:10.1039/b815894k

Reference yield: 98.6%

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide (90357-53-2) → N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide (90357-51-0)

Guidance literature:

With dihydrogen peroxide; trifluoroacetic anhydride; In dichloromethane; at 20 ℃; for 1.66667h;

DOI:10.1021/jo035377c

upstream raw materials:

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide

4-amino-2-trifluoromethylbenzonitrile

4-fluoro-2-(trifluoromethyl)benzonitrile

monoperoxyphthalic acid

Downstream raw materials:

N-(4-Cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methyl-3-(thiophen-2-ylsulfanyl)-propionamide

N-(4-Cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methyl-3-(pyridin-3-ylsulfanyl)-propionamide

N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(pyridin-2-ylthio)propanamide

3-(Benzothiazol-2-ylsulfanyl)-N-(4-cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methyl-propionamide

Refernces

• 1、 -. "Preparation method of bicalutamide". Paragraph 0033-0042. . Retrieved 2021/01/11.
• 2、 -. "Synthetic method N-(4-cyano -3-(trifluoromethyl) phenyl)-2- methyl epoxy acrylate -2- amide (by machine translation)". Paragraph 0041-0046. . Retrieved 2020/05/29.