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90357-06-5

Basic Information
CAS No.: 90357-06-5
Name: Bicalutamide
Molecular Structure:
Molecular Structure of 90357-06-5 (Bicalutamide)
Formula: C18H14F4N2O4S
Molecular Weight: 430.37
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-;
EINECS:
Density: 1.52 g/cm3
Melting Point: 191-193 °C
Boiling Point: 650.3 °C at 760 mmHg
Flash Point: 347.1 °C
Solubility: Insoluble in water
Appearance: off-white crystalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
PSA: 115.64000
LogP: 4.03338
Synthetic route
90356-78-8

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

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%
371-42-6

4-Fluorothiophenol

90357-51-0

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

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%
90356-78-8

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

A

945419-64-7

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

B

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%
455-15-2

1-(methylsufonyl)-4-fluorobenzene

87310-69-8

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

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%)
937-14-4

3-chloro-benzenecarboperoxoic acid

90356-78-8

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

90357-06-5

Bicalutamide

Conditions
ConditionsYield
In dichloromethane94%

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

90357-51-0

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

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%
371-42-6

4-Fluorothiophenol

90357-53-2

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

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%
1067225-62-0

4-cyano-3-(trifluoromethyl)phenylisocyanide

432-98-4

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

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%
824-80-6

sodium 4-fluorobenzenesulfinate

90357-51-0

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

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;
216665-25-7

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

824-80-6

sodium 4-fluorobenzenesulfinate

90357-06-5

Bicalutamide

Conditions
ConditionsYield
In dimethyl sulfoxide at 60℃; for 8h;23%

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

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
33599-22-3

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

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
371-42-6

4-Fluorothiophenol

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

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

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
90357-53-2

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

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
90357-51-0

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

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
194853-86-6

4-fluoro-2-(trifluoromethyl)benzonitrile

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
654-70-6

4-amino-2-trifluoromethylbenzonitrile

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
371-42-6

4-Fluorothiophenol

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 thiosulfate

90356-78-8

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

90357-06-5

Bicalutamide

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

[2KHSO5·KHSO4·K2SO4 salt]

sodium thiosulfate

90356-78-8

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

90357-06-5

Bicalutamide

Conditions
ConditionsYield
In methanol; water; ethyl acetate; Petroleum ether
369-51-7

4-fluorobenzenesulfinic acid

90357-51-0

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

90357-06-5

Bicalutamide

Conditions
ConditionsYield
In dimethyl sulfoxide at 50℃; pH=10; Kinetics; aq. buffer;
316373-92-9

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

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
512776-91-9

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

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
316373-95-2

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

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
316373-98-5

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

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
1679-18-1

4-Chlorophenylboronic acid

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+)

90357-51-0

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

90357-06-5

Bicalutamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water at 100℃; for 48h;
732306-64-8

bis(4-fluorophenyl)iodonium triflate

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
352-34-1

4-fluoro-1-iodobenzene

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
591-80-0

pent-4-enoic acid

90357-06-5

Bicalutamide

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

26042-63-7

silver(I) hexafluorophosphate

90357-06-5

Bicalutamide

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

Conditions
ConditionsYield
In methanol for 12h; Reflux; Darkness;61.3%

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

90357-06-5

Bicalutamide

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]

26042-63-7

silver(I) hexafluorophosphate

90357-06-5

Bicalutamide

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

Conditions
ConditionsYield
In methanol for 12h; Reflux; Darkness;52.3%
345911-20-8, 19542-80-4, 158060-65-2, 34795-02-3, 15746-57-3

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

26042-63-7

silver(I) hexafluorophosphate

90357-06-5

Bicalutamide

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

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

Bicalutamide

A

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

B

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
90357-06-5

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
90357-06-5

Bicalutamide

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
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    Bicalutamide

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    Bicalutamide 1.CAS RN: 90357-06-5 2.English Name:Bicalutimide Chemical name: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxyl-2- methylpropanemide Synonyms: Bicalutamide (Subject to

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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.

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