Product Name

  • Name

    Bicalutamide

  • EINECS
  • CAS No. 90357-06-5
  • Article Data51
  • CAS DataBase
  • Density 1.52 g/cm3
  • Solubility Insoluble in water
  • Melting Point 191-193 °C
  • Formula C18H14F4N2O4S
  • Boiling Point 650.3 °C at 760 mmHg
  • Molecular Weight 430.38
  • Flash Point 347.1 °C
  • Transport Information
  • Appearance off-white crystalline solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 90357-06-5 (Bicalutamide)
  • Hazard Symbols IrritantXi
  • Synonyms (2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methyl-propanamide;Casodex;Propanamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methyl-, (+-)-;Bicalutamide (JAN/USP);Casodex (TN);(±)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-methyl-[(4- fluorophenyl) sulfonyl]-2-hydroxy- 2-methyl propanamide;N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-fluorophenylsulfonyl)-2-hydroxy-2-methylpropanamide;Bicalutamide [USAN:BAN:INN];ICI 176334;Propanamide,N-[4-cyano-3-(trifluoromethyl)- phenyl]-3-[(4-fluorophenyl)sulfonyl]-2- hydroxy-2-methyl-;
  • PSA 115.64000
  • LogP 4.03338

Synthetic route

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
90356-78-8

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Stage #1: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide With potassium permanganate; tetra(n-butyl)ammonium hydrogensulfate In water; ethyl acetate at 25 - 30℃; for 2.5h;
Stage #2: With sodium metabisulfite In water; ethyl acetate for 1h;		100%
With (dimethyl dioctadecylammonium)3[PW12O40]; dihydrogen peroxide In dichloromethane at 25℃; for 0.416667h; Catalytic behavior; Temperature; Reagent/catalyst;99.1%
Stage #1: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide With dihydrogen peroxide; sodium tungstate; methanesulfonic acid In water; ethyl acetate at 25 - 32℃; for 6h;
Stage #2: With sodium thiosulfate In water; ethyl acetate for 0.5h; Product distribution / selectivity;		98%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

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

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Stage #1: 4-Fluorothiophenol; N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; ethyl acetate at 25 - 30℃; for 3h;
Stage #2: With potassium permanganate In water; ethyl acetate for 2.5h;
Stage #3: With sodium metabisulfite In water; ethyl acetate at 50℃; for 1h; Product distribution / selectivity;		97.3%
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
90356-78-8

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

A

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfinyl-2-hydroxy-2-methyl-propanamide
945419-64-7

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

B

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
With urea hydrogen peroxide adduct In tetrahydrofuran; formic acid; water at 27 - 35℃; for 1h;A 0.08 %Chromat.
B 96%
1-(methylsufonyl)-4-fluorobenzene
455-15-2

1-(methylsufonyl)-4-fluorobenzene

N-(4-cyano-3-(trifluoromethyl)phenyl)-2-oxo propanamide
87310-69-8

N-(4-cyano-3-(trifluoromethyl)phenyl)-2-oxo propanamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Stage #1: 1-(methylsufonyl)-4-fluorobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: N-(4-cyano-3-trifluoromethyl-phenyl)-2-oxo-propionamide In tetrahydrofuran at -78 - 20℃; Further stages.;		95%
Stage #1: 1-(methylsufonyl)-4-fluorobenzene With n-butyllithium In tetrahydrofuran for 1h;
Stage #2: N-(4-cyano-3-trifluoromethyl-phenyl)-2-oxo-propionamide In tetrahydrofuran for 0.333333h;		90%
With n-butyllithium In tetrahydrofuran1.67 g (90%)
3-chloro-benzenecarboperoxoic acid
937-14-4

3-chloro-benzenecarboperoxoic acid

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
90356-78-8

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
In dichloromethane94%
(((tert-butyldimethylsilyl)oxy)methyl)(4-fluorophenyl)sulfone

(((tert-butyldimethylsilyl)oxy)methyl)(4-fluorophenyl)sulfone

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

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
With cesium fluoride In water at 90℃; for 15h;93%
With cesium fluoride In water at 90℃; for 15h; Inert atmosphere;93%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide
90357-53-2

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Stage #1: 4-Fluorothiophenol; N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide With oxygen In acetonitrile at 45℃; for 10h;
Stage #2: With oxone In acetonitrile for 18h; Temperature; Reagent/catalyst;		88%
Stage #1: 4-Fluorothiophenol; N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide With oxygen In ethanol at 45℃; Green chemistry;
Stage #2: With Oxone In ethanol at 45℃; Green chemistry;		68%
4-cyano-3-(trifluoromethyl)phenylisocyanide
1067225-62-0

4-cyano-3-(trifluoromethyl)phenylisocyanide

1-(4-fluorophenylsulfonyl)propan-2-one
432-98-4

1-(4-fluorophenylsulfonyl)propan-2-one

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Stage #1: 4-cyano-3-(trifluoromethyl)phenylisocyanide With titanium tetrachloride In dichloromethane for 1h; Passerini reaction; Cooling with ice;
Stage #2: 1-(4-fluorophenylsulfonyl)propan-2-one In dichloromethane for 3h; Passerini reaction;
Stage #3: With water In dichloromethane for 0.333333h;		66%
sodium 4-fluorobenzenesulfinate
824-80-6

sodium 4-fluorobenzenesulfinate

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

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
With tetrabutylammomium bromide In chloroform; water for 96h; Heating / reflux;48%
With sulfuric acid In ethanol for 6h; Heating / reflux;
N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-3-iodo-2-methylpropanamide
216665-25-7

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-3-iodo-2-methylpropanamide

sodium 4-fluorobenzenesulfinate
824-80-6

sodium 4-fluorobenzenesulfinate

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
In dimethyl sulfoxide at 60℃; for 8h;23%
(4-methanesulfonyl-phenyl)-N,N,N-trimethyl-ammonium trifluoromethanesulfonate

(4-methanesulfonyl-phenyl)-N,N,N-trimethyl-ammonium trifluoromethanesulfonate

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 87 percent / tetrabutylammonium fluoride / dimethylsulfoxide / 0.5 h / 90 °C
2.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C
2.2: 95 percent / tetrahydrofuran / -78 - 20 °C
View Scheme
(4-methanesulfonylphenyl)-N,N-dimethyl-amine
33599-22-3

(4-methanesulfonylphenyl)-N,N-dimethyl-amine

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 31 percent / CH2Cl2 / 20 h / Heating
2.1: 87 percent / tetrabutylammonium fluoride / dimethylsulfoxide / 0.5 h / 90 °C
3.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C
3.2: 95 percent / tetrahydrofuran / -78 - 20 °C
View Scheme
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

o-CHO-C6H4-X (X=NO2 or F)

o-CHO-C6H4-X (X=NO2 or F)

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 2 h / 20 °C
2: 255.2 g / hydrogen peroxide; trifluoroacetic anhydride / CH2Cl2 / 16 h / 20 °C
View Scheme
N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide
90357-53-2

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98.6 percent / hydrogen peroxide; trifluoroacetic anhydride / CH2Cl2 / 1.67 h / 20 °C
2: sodium hydride / tetrahydrofuran / 2 h / 20 °C
3: 255.2 g / hydrogen peroxide; trifluoroacetic anhydride / CH2Cl2 / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: m-chloroperbenzoic acid, 2,6-di-tert-butyl-4-methylphenol / 1,1,1-trichloro-ethane / 6 h / Heating
2: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) room temperature, 16 h
3: 90 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1.1: dihydrogen peroxide; trifluoroacetic anhydride / dichloromethane / 24 h / 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 - 20 °C / Inert atmosphere
2.2: 24 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 25 °C / Inert atmosphere
View Scheme
N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide
90357-51-0

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 2 h / 20 °C
2: 255.2 g / hydrogen peroxide; trifluoroacetic anhydride / CH2Cl2 / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) room temperature, 16 h
2: 90 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 - 20 °C / Inert atmosphere
1.2: 24 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 25 °C / Inert atmosphere
View Scheme
4-fluoro-2-(trifluoromethyl)benzonitrile
194853-86-6

4-fluoro-2-(trifluoromethyl)benzonitrile

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97 percent / sodium hydride / dimethylformamide / 4 h / 20 °C
2: 98.6 percent / hydrogen peroxide; trifluoroacetic anhydride / CH2Cl2 / 1.67 h / 20 °C
3: sodium hydride / tetrahydrofuran / 2 h / 20 °C
4: 255.2 g / hydrogen peroxide; trifluoroacetic anhydride / CH2Cl2 / 16 h / 20 °C
View Scheme
4-amino-2-trifluoromethylbenzonitrile
654-70-6

4-amino-2-trifluoromethylbenzonitrile

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 81 percent / SOCl2 / N,N-dimethyl-acetamide / 0.17 h / 20 °C
2.1: BuLi / tetrahydrofuran / 1 h
2.2: 90 percent / tetrahydrofuran / 0.33 h
View Scheme
Multi-step reaction with 4 steps
1: N,N-dimethylacetamide / 4 h / Ambient temperature
2: m-chloroperbenzoic acid, 2,6-di-tert-butyl-4-methylphenol / 1,1,1-trichloro-ethane / 6 h / Heating
3: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) room temperature, 16 h
4: 90 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1.1: N,N-dimethyl acetamide / 3 h / 20 °C / Inert atmosphere
2.1: dihydrogen peroxide; trifluoroacetic anhydride / dichloromethane / 24 h / 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 - 20 °C / Inert atmosphere
3.2: 24 h / 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 25 °C / Inert atmosphere
View Scheme
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) room temperature, 16 h
2: 90 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature
View Scheme
sodium tungstate

sodium tungstate

sodium thiosulfate

sodium thiosulfate

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
90356-78-8

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
With dihydrogen peroxide In dichloromethane; ethyl acetate; Petroleum ether
...Expand
[2KHSO5·KHSO4·K2SO4 salt]

[2KHSO5·KHSO4·K2SO4 salt]

sodium thiosulfate

sodium thiosulfate

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide
90356-78-8

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
In methanol; water; ethyl acetate; Petroleum ether
...Expand
4-fluorobenzenesulfinic acid
369-51-7

4-fluorobenzenesulfinic acid

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

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
In dimethyl sulfoxide at 50℃; pH=10; Kinetics; aq. buffer;
N-[4-cyano-3-(trifluoromethyl)-phenyl]-2,3-dihydroxy-2-methyl-propionamide
316373-92-9

N-[4-cyano-3-(trifluoromethyl)-phenyl]-2,3-dihydroxy-2-methyl-propionamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane; triethylamine / 0 - 20 °C
2: sodium iodide / acetone / 48 h / Heating / reflux
3: dimethyl sulfoxide / 8 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane; triethylamine / 0.5 h / 0 - 20 °C
2: sodium iodide / acetone / 21 h / Heating / reflux
3: dimethyl sulfoxide / 8 h / 60 °C
View Scheme
N-[4-cyano-3-(trifluoromethyl)phenyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxamide
512776-91-9

N-[4-cyano-3-(trifluoromethyl)phenyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / methanol / 18 h / 20 °C
2: dichloromethane; triethylamine / 0 - 20 °C
3: sodium iodide / acetone / 48 h / Heating / reflux
4: dimethyl sulfoxide / 8 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / methanol / 18 h / 20 °C
2: dichloromethane; triethylamine / 0.5 h / 0 - 20 °C
3: sodium iodide / acetone / 21 h / Heating / reflux
4: dimethyl sulfoxide / 8 h / 60 °C
View Scheme
N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-methanesulfonyloxy-2-methyl-propionamide
316373-95-2

N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-methanesulfonyloxy-2-methyl-propionamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium iodide / acetone / 21 h / Heating / reflux
2: dimethyl sulfoxide / 8 h / 60 °C
View Scheme
(+/-)-N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-[4-methylphenyl-sulfonyloxy]-2-methyl-propionamide
316373-98-5

(+/-)-N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-[4-methylphenyl-sulfonyloxy]-2-methyl-propionamide

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium iodide / acetone / 48 h / Heating / reflux
2: dimethyl sulfoxide / 8 h / 60 °C
View Scheme
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nickel(II) bromide dimethoxyethane; 3,4,7,8-Tetramethyl-o-phenanthrolin; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; lithium tert-butoxide / 16 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / water / 48 h / 100 °C
View Scheme
C6H4ClO2S(1-)*Li(1+)

C6H4ClO2S(1-)*Li(1+)

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

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

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water at 100℃; for 48h;
bis(4-fluorophenyl)iodonium triflate
732306-64-8

bis(4-fluorophenyl)iodonium triflate

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper diacetate; ammonia / 1,2-dimethoxyethane; methanol / 1 h / 20 °C
2: cesium fluoride / water / 15 h / 90 °C
View Scheme
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

Bicalutamide
90357-06-5

Bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (2S,4R)-N-(2,6-dimethylphenyl)-4-hydroxypyrrolidine-2-carboxamide; copper(l) iodide; potassium phosphate / dimethyl sulfoxide / 24 h / 35 °C
2: cesium fluoride / water / 15 h / 90 °C
View Scheme
pent-4-enoic acid
591-80-0

pent-4-enoic acid

Bicalutamide
90357-06-5

Bicalutamide

C23H20F4N2O5S

C23H20F4N2O5S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 17h;82%
Ru(2,2'-biquinoline)dichlorid

Ru(2,2'-biquinoline)dichlorid

silver(I) hexafluorophosphate
26042-63-7

silver(I) hexafluorophosphate

Bicalutamide
90357-06-5

Bicalutamide

C72H52F8N8O8RuS2(2+)*2F6P(1-)

C72H52F8N8O8RuS2(2+)*2F6P(1-)

Conditions
ConditionsYield
In methanol for 12h; Reflux; Darkness;61.3%
...Expand
2(13)CN(1-)*Zn(2+)

2(13)CN(1-)*Zn(2+)

Bicalutamide
90357-06-5

Bicalutamide

C17(13)CH14F4N2O4S

C17(13)CH14F4N2O4S

Conditions
ConditionsYield
With C10H12O2NiC8H12-1,5-cyclo; triphenylborane; diphenyl(methyl)phosphine In 1-methyl-pyrrolidin-2-one at 80℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;57%
[Ru(1,10-phenanthroline)2Cl2]

[Ru(1,10-phenanthroline)2Cl2]

silver(I) hexafluorophosphate
26042-63-7

silver(I) hexafluorophosphate

Bicalutamide
90357-06-5

Bicalutamide

C60H44F8N8O8RuS2(2+)*2F6P(1-)

C60H44F8N8O8RuS2(2+)*2F6P(1-)

Conditions
ConditionsYield
In methanol for 12h; Reflux; Darkness;52.3%
...Expand
cis-dichlorobis(2,2′-bipyridine)ruthenium(II)
345911-20-8, 19542-80-4, 158060-65-2, 34795-02-3, 15746-57-3

cis-dichlorobis(2,2′-bipyridine)ruthenium(II)

silver(I) hexafluorophosphate
26042-63-7

silver(I) hexafluorophosphate

Bicalutamide
90357-06-5

Bicalutamide

C56H44F8N8O8RuS2(2+)*2F6P(1-)

C56H44F8N8O8RuS2(2+)*2F6P(1-)

Conditions
ConditionsYield
In methanol for 12h; Reflux; Darkness;50.6%
...Expand
Bicalutamide
90357-06-5

Bicalutamide

A

N-(4-cyano-3-(difluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methylpropanamide

N-(4-cyano-3-(difluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methylpropanamide

B

C18H16F2N2O4S

C18H16F2N2O4S

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; 1,2,2,6,6-pentamethylpiperidine; 4-sulfanylphenol; 1,3-dicyano-2,4,5,6-tetrakis(N,N-diphenylamino)-benzene In 1,2-dichloro-ethane at 25℃; for 12h; Sealed tube; Irradiation; Inert atmosphere; Overall yield = 50 percentSpectr.;A 43%
B n/a
Bicalutamide
90357-06-5

Bicalutamide

phosphoric acid ester dicalcium salt of bicalutamide

phosphoric acid ester dicalcium salt of bicalutamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran / 3 h / -78 - 0 °C
2: hydrogen / palladium 10% on activated carbon / methanol / 20 °C
3: sodium hydroxide / di-isopropyl ether; methanol / 3.5 h / 0 - 20 °C
View Scheme
Bicalutamide
90357-06-5

Bicalutamide

C18H13F4N2O7PS(2-)*2K(1+)

C18H13F4N2O7PS(2-)*2K(1+)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran / 3 h / -78 - 0 °C
2: hydrogen / palladium 10% on activated carbon / methanol / 20 °C
3: potassium hydroxide / methanol / 2 h / 0 - 20 °C
View Scheme

Bicalutamide Standards and Recommendations

 Bicalutamide (CAS NO.90357-06-5) is preventing the activation of the AR and acts as a pure anti-androgen by binding to the androgen receptor (AR) and subsequent upregulation of androgen responsive genes by androgenic hormones. In addition, bicalutamide accelerates the degradation of the androgen receptor.

Bicalutamide Specification

1. Introduction of Bicalutamide
Bicalutamide is one kind of off-white crystalline solid. Bicalutamide is practically insoluble in water. The Product Categories of this chemical is Active Pharmaceutical Ingredients;Antiandrogen;Antineoplastic (Hormonal);anti-neoplastic;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;API's. The Classification Code of Bicalutamide is Androgen antagonists; Antineoplastic; Antineoplastic agents; Drug / Therapeutic Agent; Hormone Antagonists; Hormones, Hormone Substitutes, and Hormone Antagonists; Reproductive Effect.

2. Properties of Bicalutamide
Physical properties about Bicalutamide are:
(1)XLogP3-AA: 2.3; (2)H-Bond Donor: 2; (3)H-Bond Acceptor: 9; (4)Melting Point: 191-193 °C; (5)Surface Tension: 58.2 dyne/cm; (6)Density: 1.52 g/cm3; (7)Flash Point: 347.1 °C; (8)Enthalpy of Vaporization: 100.72 kJ/mol; (9)Boiling Point: 650.3 °C at 760 mmHg; (10)Vapour Pressure: 8.47E-18 mmHg at 25°C.

3. Structure Descriptors of Bicalutamide
(1)InChI: InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)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)/t17-/m0/s1;
(2)InChIKey: InChIKey=LKJPYSCBVHEWIU-KRWDZBQOSA-N;
(3)Smiles: c1(c(ccc(c1)NC([C@@](CS(c1ccc(F)cc1)(=O)=O)(C)O)=O)C#N)C(F)(F)F.

4. Toxicity of Bicalutamide

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 2gm/kg (2000mg/kg)   Journal of Toxicological Sciences. Vol. 22, Pg. 75, 1997.
mouse LD oral > 2gm/kg (2000mg/kg)   Journal of Toxicological Sciences. Vol. 22, Pg. 75, 1997.
mouse LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 197, 2000.
rabbit LD50 oral > 200mg/kg (200mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 197, 2000.
rat LD oral > 2gm/kg (2000mg/kg)   Journal of Toxicological Sciences. Vol. 22, Pg. 75, 1997.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 197, 2000.

5. Safety information of Bicalutamide
Bicalutamide (CAS NO.90357-06-5) is contraindicated, females and children must not be given to any patient who has shown a hypersensitivity reaction to its use. 
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
 S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RIDADR: 3077
HazardClass: 9
PackingGroup: III

6. Uses of Bicalutamide
Bicalutamide is good for the treatment of stage D2 metastatic prostate cancer in combination with a luteinizing hormone-releasing hormone analogue or as a monotherapy.It has also been used in clinical trials for ovarian cancer and in combination with castration.Most advanced prostate cancer patients eventually become resistant to antiandrogen including bicalutamide therapy. Bicalutamide is contraindicated in patients who have shown a hypersensitivity reaction to its use.

7. Production of Bicalutamide
Bicalutamide can be got from Methyl methacrylate. The detailed steps of this reaction is as follows:

Production of Bicalutamide

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