90356-78-8

Basic information

• Product Name: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide
• Synonyms: (R,S)-N-[4-Cyano-3-(trifluoroMethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-MethylpropionaMide;N-[4-Cyano-3-(TrifluoroMethyl)Phenyl]-3-[(4-Fluorophenyl)thio]-2-Hydroxy-2-Methy-PropanaMide;N-[4-Cyano-3-trifluoroMethy phenyl]-S-(4-fluorophenylthio)-2-hydrdoxy-2-Methyl-propionaMide(ASH BicalutaMide);N-[4-cyano-3-(rifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2- hydroxy-2-methyl propan Amide;90356-78-8;Bicalutamide EP Impurity J;N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropiomide;4-CYANO-3-TRIFLUOROMETHYL-N-[3-(4-FLUOROPHENYLTHIO)-2-HYDROXYL-2-METHYLPROPIONYL]ANILINE
• CAS NO: 90356-78-8
• Molecular Formula: C₁₈H₁₄F₄N₂O₂S
• Molecular Weight: 398.37
• EINECS: 1312995-182-4
• Product Categories: (intermediate of bicalutamide);Bicalutamide;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 90356-78-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 109-111°C
• Boiling Point: 565.588 °C at 760 mmHg
• Flash Point: 295.857 °C
• Appearance: off-white crystalline powder
• Density: 1.43 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.31±0.29(Predicted)
• CAS DataBase Reference: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide(90356-78-8)
• EPA Substance Registry System: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide(90356-78-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 90356-78-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Bicalutamide intermediate.

InChI:InChI=1/C18H14F4N2O2S/c1-17(26,10-27-14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

Upstream product

• 35337-66-7 4-fluorobenzenethiolate 
• 90357-51-0 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 300627-43-4 2-iodo-4-nitrobenzonitrile 
• 540-51-2 2-bromoethanol 
• 300627-48-9 4-amino-2-iodobenzonitrile 
• 371-42-6 4-Fluorothiophenol 
• 90357-53-2 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide 
• 3887-61-4 sodium 4-fluorophenylthiolate 
• 316373-95-2 N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-methanesulfonyloxy-2-methyl-propionamide 
• 7440-44-0 pyrographite 
• 339530-91-5 3-(4-Fluoro-phenylsulfanyl)-2-hydroxy-2-methyl-propionic acid 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 873014-32-5 N-[4-cyano-3-(trifluoromethyl)-phenyl-]-3-[4-fluorophenylthio]-2-acetoxy-2-methyl-propionamide 

Downstream Products

• 90357-06-5 Bicalutamide 
• 945419-64-7 N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfinyl-2-hydroxy-2-methyl-propanamide 
• 113299-39-1 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid 1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-2-(4-fluoro-phenylsulfanyl)-1-methyl-ethyl ester 

Relevant articles and documents

Nucleophilic Aromatic Substitution of Methacrylamide Anion and Its Application to the Synthesis of the Anticancer Drug Bicalutamide

The anticancer drug (R,S)-biscaltamide was prepared in three steps in >90% overall yield. A key step in the new synthesis involved a new nucleophilic aromatic substitution reaction of methacrylamide anion.

Preparation method of bicalutamide thioether intermediate

The invention relates to a preparation method of a bicalutamide thioether intermediate, and relates to the synthesis of chemical drugs, in particular to a preparation method of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[4-fluorophenylthio]-2-hydroxy-2-methylpropionamide. According to the method, a lower fatty acid ester is taken as a solvent, an alkali metal salt of a lower aliphatic alcohol is taken as a catalyst, 4-fluorothiophenol first reacts with the alkali metal salt of the lower aliphatic alcohol to generate 4-fluorfenthiolate, then N-[4-cyano-3-(trifluoromethyl)phenyl]-1,2-epoxy-2-methylpropionamide is added into 4-fluorfenthiolate for a reaction at room temperature, and a finished product is obtained after separation and purification. The preparation method provided by the inventionis mild in reaction conditions, the use of high-risk sodium hydride and expensive tetrahydrofuran is avoided, and a reaction solvent can also be recycled and reused, thereby reducing cost and reducing emissions.

Auto-oxidative hydroxysulfenylation of alkenes

One-pot auto-oxidation mediated hydroxysulfenylation of electron-deficient and electron-rich olefins with phenthiols was explored. The method illustrates a selective and convenient synthesis of complex β-hydroxysulfides using O2 as both the oxidant and the oxygen source under mild transition-metal-free conditions. The application of this new methodology to the gram-scale synthesis of anti-cancer drug bicalutamide has been accomplished in a two-step sequence with 71% overall yield. A plausible radical involved mechanism is proposed.