Desfluoro Bicalutamide

Base Information

• Chemical Name: Desfluoro Bicalutamide
• CAS No.: 90357-05-4
• Molecular Formula: C₁₈H₁₅F₃N₂O₄S
• Molecular Weight: 412.389
• European Community (EC) Number: 672-576-7
• UNII: 15LQ88H10F
• Nikkaji Number: J2.721.698F
• Wikidata: Q27251730
• ChEMBL ID: CHEMBL173185
• Mol file: 90357-05-4.mol

Synonyms:Desfluoro Bicalutamide;90357-05-4;UNII-15LQ88H10F;(+/-)-Desfluoro bicalutamide;N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(phenylsulfonyl)propanamide;Bicalutamide impurity A [EP];3-(BENZENESULFONYL)-N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-2-HYDROXY-2-METHYLPROPANAMIDE;15LQ88H10F;(2RS)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(phenylsulfonyl)propanamide;Propanamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(phenylsulfonyl)-;Propanamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(phenylsulfonyl)-, (+/-)-;(2RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-3-(phenylsulfonyl)propanamide;CHEMBL173185;SCHEMBL4176657;GDXNOJUTJPBYEC-UHFFFAOYSA-N;MFCD24386587;AKOS025149217;(+/-)-N-[4-Cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-3-(phenylsulfonyl)propanamide;BS-24869;BICALUTAMIDE IMPURITY A [EP IMPURITY];CS-0207771;FT-0666012;Q27251730;N-[3-(Trifluoromethyl)-4-cyanophenyl]-2-hydroxy-2-[(phenylsulfonyl)methyl]propionamide

Chemical Property of Desfluoro Bicalutamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 175-178 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 656.067oC at 760 mmHg
• PKA: 11.22±0.29(Predicted)
• Flash Point: 350.577oC
• PSA: 119.13000
• Density: 1.482g/cm3
• LogP: 4.47078
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly, Sonicated), Methanol (Sparingly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 412.07046262
• Heavy Atom Count: 28
• Complexity: 719

Purity/Quality:

99%+, ^*data from raw suppliers

DesfluoroBicalutamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CS(=O)(=O)C1=CC=CC=C1)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
• Uses: Desfluoro Bicalutamide (Bicalutamide EP Impurity A) is an impurity of Bicalutamide, a nonsteroidal antiandrogen. Bicalutamide impurity. A nonsteroidal antiandrogen.

Technology Process of Desfluoro Bicalutamide

There total 6 articles about Desfluoro 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:

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[phenylthio]-2-hydroxy-2-methyl-propanamide (90356-00-6) → N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(phenyl)sulfonyl-2-hydroxy-2-methyl-propanamide (90357-05-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jm00400a011

Reference yield:

1-(phenylsulfanyl)acetone (5042-53-5) → N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(phenyl)sulfonyl-2-hydroxy-2-methyl-propanamide (90357-05-4)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄ / H₂O / 16 h / Ambient temperature

2: conc. HCl, glacial AcOH / 24 h / Heating

3: 1.) SOCl₂, N,N-dimethylacetamide / 1.) -15 deg C, 15 min, 2.) -15 deg C, 15 min; room temperature, 16 h

4: m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / Ambient temperature

With hydrogenchloride; thionyl chloride; N,N-dimethyl acetamide; sulfuric acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water;

DOI:10.1021/jm00400a011

Reference yield:

α-hydroxy-β-phenylsulfanyl-isobutyric acid (90357-22-5) → N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(phenyl)sulfonyl-2-hydroxy-2-methyl-propanamide (90357-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) SOCl₂, N,N-dimethylacetamide / 1.) -15 deg C, 15 min, 2.) -15 deg C, 15 min; room temperature, 16 h

2: m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / Ambient temperature

With thionyl chloride; N,N-dimethyl acetamide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jm00400a011

upstream raw materials:

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[phenylthio]-2-hydroxy-2-methyl-propanamide

1-(phenylsulfanyl)acetone

α-hydroxy-β-phenylsulfanyl-isobutyric acid

thiophenol

Refernces

• 1、 -. "Method of treatment for prostatic cancer". . . Retrieved 2008/06/13.
• 2、 -. "AMIDE DERIVATIVES". . . Retrieved 2008/06/13.