N-(3-iodo-4-nitrophenyl)isobutyramide
Flutamide
Conditions | Yield |
---|---|
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; silver fluoride In N,N-dimethyl-formamide at 100℃; Sealed tube; Inert atmosphere; | 99% |
4-bromo-1-nitro-2-(trifluoromethyl)benzene
Flutamide
Conditions | Yield |
---|---|
Stage #1: potassium (2-methyl-1-((trimethylsilyl)oxy)propylidene)amide With tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane at 100℃; for 0.166667h; Stage #2: 4-bromo-1-nitro-2-(trifluoromethyl)benzene In 1,4-dioxane at 100℃; for 16h; | 86% |
2-methyl-N-[3-(trifluoromethyl)phenyl]propionamide
Flutamide
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at -5℃; for 3h; | 83.3% |
With sulfuric acid; nitric acid at 0 - 5℃; for 3h; | 79% |
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 5h; Ionic liquid; | 69% |
Conditions | Yield |
---|---|
With 6Zr(4+)*4O(2-)*6C14H8N2O4(2-)*4HO(1-) In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Sealed tube; Inert atmosphere; | 53% |
3-trifluoromethylaniline
Flutamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: cyanuric chloride; N-methylmorpholine / CH2Cl2 / 5 h / 0 - 5 °C 1.2: 20.0 g / CH2Cl2 / 3 h / 20 °C 2.1: 79 percent / sulfuric acid; nitric acid / 3 h / 0 - 5 °C View Scheme |
α,α,α-trifluorotoluene
Flutamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 3 h / 20 °C 2: iron / 4 h / Reflux; Inert atmosphere 3: sulfuric acid; nitric acid / 3 h / 0 - 5 °C View Scheme |
2,4-diaminonitrobenzene
Flutamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dmap / dichloromethane / 20 °C 2: isopentyl nitrite; copper(l) iodide / acetonitrile / 0 - 20 °C 3: copper(l) iodide; silver fluoride; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 100 °C / Sealed tube; Inert atmosphere View Scheme |
Flutamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopentyl nitrite; copper(l) iodide / acetonitrile / 0 - 20 °C 2: copper(l) iodide; silver fluoride; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 100 °C / Sealed tube; Inert atmosphere View Scheme |
4-nitro-3-(trifluoromethyl)benzeneamine
Thioisobutyric acid S-pyridin-2-yl ester
Flutamide
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 2h; Glovebox; Inert atmosphere; Sealed tube; | 15.4 mg |
Flutamide
2-methyl-N-[4-amino-3-(trifluoromethyl)phenyl]propanamide
Conditions | Yield |
---|---|
With borane-ammonia complex; jacquesdietrichite In d(4)-methanol; water-d2 at 20℃; for 1h; | 99% |
With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 21h; Autoclave; | 97% |
With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 21h; Autoclave; | 97% |
Flutamide
bromoacetic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Flutamide With sodium hydride In N,N-dimethyl-formamide for 0.75h; Inert atmosphere; Cooling with ice; Stage #2: bromoacetic acid methyl ester In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; water In acetonitrile at 20℃; for 18h; Irradiation; | 90% |
Conditions | Yield |
---|---|
With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere; | 77% |
Flutamide
Conditions | Yield |
---|---|
With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere; | 77% |
Flutamide
4-Chlorophenylboronic acid
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium pyrosulfite; isopropyl alcohol at 70℃; for 48h; Sealed tube; Inert atmosphere; | 75% |
With 1,10-Phenanthroline; potassium pyrosulfite; tetrakis(acetonitrile)copper(I) hexafluorophosphate In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 70℃; for 48h; Inert atmosphere; Sealed tube; |
Conditions | Yield |
---|---|
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation; | 72% |
thiophene boronic acid
Flutamide
Conditions | Yield |
---|---|
With potassium pyrosulfite; tetrabutyl-ammonium chloride; potassium carbonate In acetonitrile at 130℃; for 24h; Sealed tube; | 69% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; water In acetonitrile at 20℃; for 11.5h; Irradiation; | 50% |
Flutamide
A
4-nitro-3-(trifluoromethyl)benzeneamine
B
N-[4-amino-3-(trifluoromethyl)phenyl]acetamide
C
2-methyl-N-[4-amino-3-(trifluoromethyl)phenyl]propanamide
Conditions | Yield |
---|---|
With Rhodotorula mucilaginosa (ATCC 20129) In N,N-dimethyl-formamide at 20℃; for 336h; Physiological pH; Microbiological reaction; | A 11.1% B 3% C 3.3% |
Flutamide
A
4-nitro-3-(trifluoromethyl)benzeneamine
Conditions | Yield |
---|---|
With β‐cyclodextrin In phosphate buffer pH=7.4; Quantum yield; Irradiation; | |
With β‐cyclodextrin In phosphate buffer pH=7.4; Irradiation; |
Flutamide
Conditions | Yield |
---|---|
In phosphate buffer pH=7.4; Quantum yield; Irradiation; | |
In phosphate buffer pH=7.4; Irradiation; | |
With water for 2h; pH=7.4; Quantum yield; UV-irradiation; Inert atmosphere; aq. phosphate buffer; |
Flutamide
Conditions | Yield |
---|---|
With benzenesulfonamide In phosphate buffer pH=7.4; Product distribution; Further Variations:; irradiation time; absence of regent; Irradiation; | |
With L-α-Phosphatidylcholine In various solvent(s) Quantum yield; Photolysis; | |
Multi-step reaction with 2 steps 1: water; ammonium chloride; zinc / methanol / 1.5 h 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C View Scheme |
Flutamide
4-nitro-3-(trifluoromethyl)benzeneamine
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; | |
With sodium hydroxide In ice-water; ethanol | |
With hydrogenchloride In methanol; water at 100℃; for 0.4h; Kinetics; Activation energy; Reagent/catalyst; Temperature; pH-value; | |
With sodium hydroxide In methanol; water at 80℃; for 3h; Kinetics; Activation energy; Reagent/catalyst; Temperature; Concentration; |
Flutamide
4'-Nitro-3'-trifluoromethylisobutyrthioanilide
Conditions | Yield |
---|---|
With sodium hydroxide; sulfuric acid In toluene; benzene | |
With sodium hydroxide; sulfuric acid In toluene; benzene |
Flutamide
Conditions | Yield |
---|---|
With water; bovine serum albumin Quantum yield; Reagent/catalyst; UV-irradiation; Inert atmosphere; aq. phosphate buffer; |
Flutamide
isopropyl alcohol
A
2,3-dimethyl-2,3-butane diol
B
2-methyl-N-[3-(trifluoromethyl)phenyl]propionamide
Conditions | Yield |
---|---|
Irradiation; High pressure; |
Flutamide
isopropyl alcohol
A
2-methyl-N-[3-(trifluoromethyl)phenyl]propionamide
C
2-methyl-N-[4-amino-3-(trifluoromethyl)phenyl]propanamide
Conditions | Yield |
---|---|
With oxygen Irradiation; High pressure; |
Flutamide
A
2-methyl-N-[3-(trifluoromethyl)phenyl]propionamide
B
2-methyl-N-[4-amino-3-(trifluoromethyl)phenyl]propanamide
Conditions | Yield |
---|---|
With oxygen In acetonitrile Irradiation; High pressure; |
Flutamide
Conditions | Yield |
---|---|
With oxygen In acetonitrile Irradiation; High pressure; |
Flutamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonium chloride; zinc / methanol / 1 h / 20 °C 2: 0.03 h / Irradiation; High pressure View Scheme |
Flutamide
Conditions | Yield |
---|---|
In acetonitrile Irradiation; High pressure; | 43 mg |
The Flutamide, with the cas registry number 13311-84-7, has the IUPAC name of 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide. Being a kind of light yellow solid, it is nearly insoluble in water, and it is usually used as the Antiandrogen and antineoplastic (hormonal). Besides, its product categories are including Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; APIs; Antitumors for Research and Experimental Use; Biochemistry; Amines; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals; API's.
The characteristics of this chemical are as follows: (1)ACD/LogP: 3.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.72; (4)ACD/LogD (pH 7.4): 3.72; (5)ACD/BCF (pH 5.5): 392.97; (6)ACD/BCF (pH 7.4): 392.97; (7)ACD/KOC (pH 5.5): 2504.06; (8)ACD/KOC (pH 7.4): 2504.05; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 66.13; (13)Index of Refraction: 1.52; (14)Molar Refractivity: 61.27 cm3; (15)Molar Volume: 201.2 cm3; (16)Polarizability: 24.29 ×10-24 cm3; (17)Surface Tension: 38.2 dyne/cm; (18)Density: 1.372 g/cm3; (19)Flash Point: 195.9 °C; (20)Enthalpy of Vaporization: 65.11 kJ/mol; (21)Boiling Point: 400.3 °C at 760 mmHg; (22)Vapour Pressure: 1.29E-06 mmHg at 25°C; (23)Exact Mass: 276.072177; (24)MonoIsotopic Mass: 276.072177; (25)Topological Polar Surface Area: 74.9; (26)Heavy Atom Count: 19; (27)Formal Charge: 0; (28)Complexity: 352.
The production method of this chemical is as below: After the nitrification of benzenyl trifluoride to have m-nitrotrifluorinemethylbenzene, and then restore to have m-trifluorinemethylaniline; Next react with iso-butyryl chloride and then go through the nitrification to produce Flutamide.
As to its usage, it is widely applied in many ways. It could be used as the NAISD male sex hormone antagonist which could restrain teststrone transforming into dihydro-testosterone; It could also be used in curing the diseases of PCa(prostatic cancer) and prostatic hyperplasia.
When you are dealing with this chemical, you should be very careful and then take some measures to protect yourself. For one thing, it is irritant which may cause inflammation to the skin or other mucous membranes, and it is irritating to rritating to eyes, respiratory system and skin. For another thing, it is harmful that may cause damage to health. If by inhalation, in contact with skin and if swallowed, it will be dangerous. Then it will have possible risk of harm to the unborn child. Therefore, you should take the following instructions. Wear suitable protective clothing, gloves and eye/face protection, and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Do remember not to breathe dust and if contacting with this chemical, take off immediately all contaminated clothing.
Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
(2)InChI: InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
(3)InChIKey: MKXKFYHWDHIYRV-UHFFFAOYSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | > 2gm/kg (2000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: OTHER CHANGES LIVER: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 45, Pg. 135, 1993. |
man | TDLo | oral | 310mg/kg/31D- (310mg/kg) | BEHAVIORAL: EUPHORIA | American Journal of Psychiatry. Vol. 143, Pg. 1498, 1986. |
rat | LD50 | intraperitoneal | 289mg/kg (289mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Oyo Yakuri. Pharmacometrics. Vol. 45, Pg. 135, 1993. |
rat | LD50 | oral | 787mg/kg (787mg/kg) | KIDNEY, URETER, AND BLADDER: HEMATURIA KIDNEY, URETER, AND BLADDER: INCONTINENCE | Oyo Yakuri. Pharmacometrics. Vol. 45, Pg. 135, 1993. |
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