(R)-Bicalutamide

Base Information

• Chemical Name: (R)-Bicalutamide
• CAS No.: 113299-40-4
• Molecular Formula: C₁₈H₁₄F₄N₂O₄S
• Molecular Weight: 430.38
• Mol file: 113299-40-4.mol

Synonyms:Propanamide,N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-,(R)-;(R)-Casodex;R-Bicalutimide;

Chemical Property of (R)-Bicalutamide

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 8.47E-18mmHg at 25°C
• Melting Point: 178-181 °C
• Refractive Index: 1.577
• Boiling Point: 650.3 °C at 760 mmHg
• PKA: 11.49±0.29(Predicted)
• Flash Point: 347.1 °C
• PSA: 115.64000
• Density: 1.52 g/cm³
• LogP: 4.03338
• Storage Temp.: -20?C Freezer
• Solubility.: Acetone (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Bicalutamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-Bicalutamide can be used as an antiandrogen, antineoplastic (hormonal).

Technology Process of (R)-Bicalutamide

There total 11 articles about (R)-Bicalutamide 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: 96.8%

(R)-Thiobicalutamide → (R)-bicalutamide (90357-06-5,113299-38-0,151262-58-7,113299-40-4)

Guidance literature:

With sodium tungstate; dihydrogen peroxide; In acetone; at 5 ℃; Reflux;

Reference yield: 91.0%

C10H11FO5S (890658-79-4) + 4-amino-2-trifluoromethylbenzonitrile (654-70-6) → (R)-bicalutamide (90357-06-5,113299-38-0,151262-58-7,113299-40-4)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; at 20 ℃; for 120h;

DOI:10.1016/j.tetlet.2006.12.011

Reference yield:

sodium 4-fluorobenzenesulfinate (824-80-6) → (R)-bicalutamide (90357-06-5,113299-38-0,151262-58-7,113299-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-hydroxyphthalimide; diisopropyl-carbodiimide; dmap / dichloromethane / 20 °C / Sealed tube

1.2: 12 h / 20 °C / Inert atmosphere; Irradiation

2.1: potassium hydroxide / methanol; water / 2 h / 220 °C

3.1: N,N-dimethyl acetamide / 3 h / -10 °C / Inert atmosphere

3.2: 16 h / 20 °C / Inert atmosphere

With dmap; N-hydroxyphthalimide; N,N-dimethyl acetamide; potassium hydroxide; diisopropyl-carbodiimide; In methanol; dichloromethane; water;

DOI:10.1016/j.chempr.2020.02.003

upstream raw materials:

C₁₀H₁₁FO₅S

4-amino-2-trifluoromethylbenzonitrile

C₁₇H₁₉FO₂S

C₁₇H₁₉FO₄S

Downstream raw materials:

phosphoric acid ester of (R)-bicalutamide

O-dibenzyl phosphoric acid ester of (R)-bicalutamide

Refernces

• 1、 Ichikawa, Yuki,Hiramatsu, Michiaki,Mita, Yusuke,Makishima, Makoto,Matsumoto, Yotaro,Masumoto, Yui,Muranaka, Atsuya,Uchiyama, Masanobu,Hashimoto, Yuichi,Ishikawa, Minoru. "Meta -Non-flat substituents: A novel molecular design to improve aqueous solubility in small molecule drug discovery". supporting information. p. 446 - 456. Retrieved 2021/01/29.
• 2、 Chen, Guangle,Chen, Jia-Rong,He, Jiayan,Li, Chaozhong,Li, Yi,Liu, Feng,Xiao, Wen-Jing,Zhang, Benxiang. "Catalytic Decarboxylative Radical Sulfonylation". supporting information. p. 1149 - 1159. Retrieved 2020/05/13.