87310-69-8

Basic information

• Product Name: N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide
• Synonyms: N-(4-Cyano-3-trifluoromethyl-phenyl]-2-oxo-propionamide;N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide
• CAS NO: 87310-69-8
• Molecular Formula: C₁₁H₇F₃N₂O₂
• Molecular Weight: 256.1806896
• Product Categories: Chemical Amines;Amines;Aromatics
• Mol File: 87310-69-8.mol

Chemical Properties

• Melting Point: 147-1480C
• Appearance: /
• Density: 1.401g/cm³
• Refractive Index: 1.503
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.71±0.70(Predicted)
• CAS DataBase Reference: N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide(87310-69-8)
• EPA Substance Registry System: N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide(87310-69-8)

Safety Data

• Hazardous Substances Data: 87310-69-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide is utilized as a key intermediate in organic synthesis for the creation of a range of chemical compounds. Its presence in the synthesis process can lead to the formation of pharmaceuticals, agrochemicals, and other specialty chemicals that have diverse applications across different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide is used as a building block for the development of new drugs. Its unique structure can be incorporated into drug molecules to enhance their efficacy, selectivity, and pharmacokinetic properties, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide serves as a precursor for the synthesis of new pesticides or herbicides. Its incorporation into these chemical products can improve their effectiveness in controlling pests and weeds, thereby contributing to increased crop yields and agricultural productivity.
Used in Specialty Chemicals:
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-oxopropanamide is also used in the production of specialty chemicals, which are high-value compounds used in specific applications such as materials science, coatings, dyes, and more. Its unique properties can contribute to the development of innovative products with improved performance characteristics.

InChI:InChI=1/C11H7F3N2O2/c1-6(17)10(18)16-8-3-2-7(5-15)9(4-8)11(12,13)14/h2-4H,1H3,(H,16,18)

Upstream product

• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 5704-66-5 pyruvoyl chloride 
• 127-17-3 2-oxo-propionic acid 

Downstream Products

• 90357-06-5 Bicalutamide 
• 929029-21-0 C₂₀H₂₀F₃N₃O₄S 
• 1373493-06-1 (S(S),S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-(-1,1-dimethylethylsulfinamido)-3-(4-fluorophenylsulfonyl)-2-methylpropanamide 
• 1239670-03-1 (S)-4-(4-((4-cyanophenoxy)methyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 
• 1239669-89-6 (S)-2-amino-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-methylpropanamide 
• 1373493-15-2 [S(S),S]-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-((S)-1,1-dimethylethylsulfinamido)-2-methylpropanamide 
• 1373493-13-0 C₁₈H₁₅F₄N₃OS 
• 1373493-12-9 C₂₂H₂₃F₄N₃O₂S₂ 
• 1373493-11-8 [S(S),R]-(tert-butylsulfinyl)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methylziridine-2-carboxamide 
• 1373493-14-1 [S(S),S]-(tert-butylsulfinyl)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methylziridine-2-carboxamide 
• 1373493-10-7 (S)-4-(4-((4-fluorophenylsulfonyl)methyl)-4-methyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 
• 1373493-09-4 (R)-4-(4-((4-fluorophenylsulfonyl)methyl)-4-methyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 
• 1239670-13-3 (S)-4-(4-((4-fluorophenylsulfonyl)methyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoro methyl)benzonitrile 
• 1239670-02-0 (R)-4-(4-((4-fluorophenylsulfonyl)methyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoro methyl)benzonitrile 

Relevant articles and documents

A two-step synthesis of the anti-cancer drug (R,S)-bicalutamide

A short, efficient synthesis of the non-steroidal antiandrogen (R,S)-bicalutamide is presented. This new route generates bicalutamide in only two steps with an overall yield of 73%. The key step is a 1,2 addition of a methyl sulfone to a keto-amide.

Synthesis and biological evaluation of [18F]bicalutamide, 4-[76Br]bromobicalutamide, and 4-[76Br]bromo- thiobicalutamide as non-steroidal androgens for prostate cancer imaging

Androgen receptors (AR) are overexpressed in most primary and metastatic prostate cancers. To develop a nonsteroidal AR-mediated imaging agent, we synthesized and radiolabeled several analogs of the potent antiandrogen bicalutamide: [18F]bicalutamide, 4-[76Br] bromobicalutamide, and [76Br]bromo-thiobicalutamide. Two of these analogs, 4-[76Br]bromobicalutamide and [76Br]bromo- thiobicalutamide, were found to have a substantially increased affinity for the androgen receptor (AR) compared to that of bicalutamide. The synthesis of [ 18F]bicalutamide utilized a pseudocarrier approach to effect addition of a carbanion generated from tracer-level amounts of a radiolabeled precursor to an unlabeled carbonyl precursor. 4-[76Br]Bromobicalutamide and [76Br]bromo-thiobicalutamide were labeled through electrophilic bromination of a tributylstannane precursor. The former could be prepared in high specific activity, and its tissue distribution was tested in vivo. Androgen target tissue uptake was evident in castrated adult male rats; however, in DES-treated, AR-positive, tumor-bearing male mice, tumor uptake was low.

METHODS OF SYNTHESIZING ACYLANILIDES INCLUDING BICALUTAMIDE AND DERIVATIVES THEREOF

Methods of synthesizing an acylanilide include contacting a compound having the structure of Formula I: with a compound having the structure of Formula II: under conditions sufficient to provide a compound having the structure of Formula III: and treating the compound of Formula III under conditions sufficient to provide an acylanilide. The compound of Formula III may be addition reacted with a compound having the structure of Formula IV: R5—X1—R6—R7??Formula IV under conditions sufficient to provide an acylanilide having the structure of Formula V: