Sorafenib supplier | CasNO.284461-73-0

Name
Sorafenib tosylate
EINECS 608-209-4
CAS No. 284461-73-0
Article Data59
CAS DataBase
Density 1.454 g/cm³
Solubility 100μg/L at 20℃
Melting Point 202-204 °C
Formula C₂₁H₁₆ClF₃N₄O₃
Boiling Point 523.3 °C at 760 mmHg
Molecular Weight 464.831
Flash Point 270.3 °C
Transport Information
Appearance light yellow solid
Safety 36-37-39
Risk Codes 68/20/21/22-37/38
Molecular Structure
Hazard Symbols Xi
Synonyms BAY43-9006;N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea;
PSA 92.35000
LogP 6.08660

Synthetic route

: 343247-69-8
4-chloro-3-trifluoromethylphenylurea

: 1154243-75-0
[4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: [4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 20℃; for 0.5h; Stage #2: 4-chloro-3-trifluoromethylphenylurea In 1,4-dioxane at 80 - 100℃; for 1h; Solvent; Reagent/catalyst;	97.9%
With t-BuBrettPhos; palladium diacetate; caesium carbonate In tetrahydrofuran; water at 75℃; for 5h; Inert atmosphere;	206 mg

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: (4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With 1-Methylpyrrolidine In dichloromethane at 30℃; for 24h; Solvent; Temperature;	97.6%

: 1129683-83-5
4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

: 1209459-88-0
4-bromo-pyridine-2-carboxylic acid methyl amide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 50 - 60℃; for 0.5h; Stage #2: 4-bromo-pyridine-2-carboxylic acid methyl amide In 1-methyl-pyrrolidin-2-one for 2h; Reagent/catalyst; Reflux;	96.7%

: 611226-36-9, 1061231-84-2
4-hydroxy-N-methylpyridine-2-carboxamide

: 1129683-83-5
4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
at 132℃;	96.3%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 327-78-6
4-chloro-3-(trifluoromethyl)phenyl isocyanate

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With zirconia grinding balls In acetonitrile for 4h; Milling;	96%
In ethyl acetate at 20 - 30℃; Large scale;	94.2%
In dichloromethane	93%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1187086-96-9
N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
In chlorobenzene at 70 - 75℃; for 0.25h; Product distribution / selectivity;	95%
In ethyl acetate at 20 - 50℃; for 2.75h;	77%
With potassium carbonate In dichloromethane for 8h; Milling;	72%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1737-36-6
4-chloro-3-(trifluoromethyl)benzoic acid

: 2,2,2,-trichloroethoxycarbonyl azide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 2,2,2,-trichloroethoxycarbonyl azide With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Curtius Rearrangement; Inert atmosphere; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	93%

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 530-62-1
1,1'-carbonyldiimidazole

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane Inert atmosphere;	91%
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 25 - 35℃; for 18h; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane at 25 - 35℃; for 48.75h;	90 g

...Expand

: 123-30-8
4-amino-phenol

: 327-78-6
4-chloro-3-(trifluoromethyl)phenyl isocyanate

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-amino-phenol; 4-chloro-3-(trifluoromethyl)phenyl isocyanate; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃; Solvent; Reagent/catalyst; Temperature;	90.6%

...Expand

: 1129683-83-5
4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With potassium carbonate In toluene Heating;	90%
With tetrabutylammomium bromide; potassium iodide; potassium hydroxide In tetrahydrofuran at 80℃; for 10h; Solvent; Reagent/catalyst;	89.4%
Stage #1: 4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol With potassium tert-butylate In N,N-dimethyl-formamide for 2h; Stage #2: 4-chloro-N-methylpicolinamide With potassium carbonate at 80℃; for 6h;	50%

: 827025-43-4
4-(2-methylcarbamoyl-pyridin-4-yloxy)-benzoic acid

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In water at 30 - 100℃;	90%

: 1187086-96-9
N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

: 123-30-8
4-amino-phenol

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide; 4-amino-phenol; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃;	88.5%

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1737-36-6
4-chloro-3-(trifluoromethyl)benzoic acid

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In water at 30 - 100℃;	88%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 3-(4-chloro-3-(trifluoromethyl)phenyl)-1,4,2-dioxazol-5-one

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With sodium acetate In methanol at 60℃; for 2h;	86%

: 348-91-4
N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride

: 123-30-8
4-amino-phenol

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride; 4-amino-phenol; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃;	85.5%

...Expand

: 123-30-8
4-amino-phenol

: 871555-75-8
(4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester

: 220000-87-3
4-chloro-N-methylpicolinamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Stage #1: 4-amino-phenol; (4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃;	85.4%

...Expand

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: C7H3ClF3NO

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 0.25h; Inert atmosphere;	85%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 2,2,2-trichloroethyl (4-chloro-3-(trifluoromethyl)phenyl)carbamate

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; acetonitrile at 100℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;	80%

: 1012058-78-4
4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-2-pyridinecarboxylic acid

: 593-51-1
methylamine hydrochloride

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	63.2%

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 871555-75-8
(4-chloro-3-trifluoromethylphenyl)carbamic acid phenyl ester

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With pyridine at 80℃; for 3h;	48.2%
In N,N-dimethyl-formamide at 40 - 45℃; for 2 - 3h; Product distribution / selectivity;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40 - 45℃;

: sorafenib tosylate

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
at 200℃;

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 343247-69-8
4-chloro-3-trifluoromethylphenylurea

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 110 - 120℃; for 12 - 18h; Product distribution / selectivity;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 110 - 120℃;

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 1129683-96-0
1-(4-chloro-3-(trifluoromethyl)phenyl)-3-hydroxyurea

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 125℃; for 96h; Product distribution / selectivity;
With triethylamine In N,N-dimethyl-formamide at 125℃; for 96h;

: 284462-37-9
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

: 13692-04-1
2,2,2-trichloro-N-(4-chloro-3-(trifluoromethyl)phenyl)acetamide

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Product distribution / selectivity; Heating / reflux;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Reflux;

: 1129683-88-0
N-methyl-4-(4-ureidophenoxy)picolinamide

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Product distribution / selectivity; Heating / reflux;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h; Reflux;

: 1129683-92-6
phenyl 4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenylcarbamate

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
In acetonitrile for 24h; Product distribution / selectivity; Heating / reflux;
In acetonitrile for 24h; Reflux;

: 1129683-94-8
N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamide

: 320-51-4
4-chloro-3-trifluoromethyl-aniline

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 110℃; for 8 - 9h; Product distribution / selectivity;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 110℃;

: C17H16ClF3N2O3

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; water / 1 h / 40 °C / Inert atmosphere 2: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 5 h / 75 °C / Inert atmosphere View Scheme

: 445-01-2
5-bromo-2-chlorobenzotrifluoride

: 284461-73-0
sorafenib

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 2 h / 85 °C / Inert atmosphere 2: hydrogenchloride; water / 1 h / 40 °C / Inert atmosphere 3: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 5 h / 75 °C / Inert atmosphere View Scheme

: 3144-16-9
(1S)-10-camphorsulfonic acid

: 284461-73-0
sorafenib

: 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methylpyridine-2-carboxamide hemicamsylate

Conditions

Conditions	Yield
In tert-butyl methyl ether at 15 - 50℃; Solvent; Temperature;	99.4%

: 75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9
cis-dichlorobis(dimethylsulfoxide)platinum(II)

: 284461-73-0
sorafenib

: C23H22Cl3F3N4O4PtS

Conditions

Conditions	Yield
In methanol; acetone at 45℃; for 28h; Solvent; Temperature;	98%

: 2835-81-6
2-aminobutanoic acid

: 284461-73-0
sorafenib

: sorafenib α-aminobutyrate

Conditions

Conditions	Yield
In water; isopropyl alcohol at 75℃; for 3h; Solvent; Temperature;	97.9%

: 284461-73-0
sorafenib

: 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide sulphate

Conditions

Conditions	Yield
With sulfuric acid In butanone at 26℃; for 5h; Product distribution / selectivity;	90.9%

: 284461-73-0
sorafenib

: 1280217-32-4
4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N-methylpyridine-2-carboxamide sulphate

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 20 - 60℃; for 12h;	89%

: 594-45-6
ethanesulfonic acid

: 284461-73-0
sorafenib

: 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide ethanesulphonate

Conditions

Conditions	Yield
In butanone at 26℃; for 3h;	88.9%

: 104-15-4
toluene-4-sulfonic acid

: 284461-73-0
sorafenib

: N-[4-chloro-3-(trifluoromethyl)phenyl]-N′-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea p-toluenesulfonate

Conditions

Conditions	Yield
In water; acetonitrile Reflux;	87.6%
In methanol at 40 - 65℃;	84.5%
In acetonitrile at 26℃; for 2h;	78.2%

: 284461-73-0
sorafenib

: 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]-carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; butanone at -10 - -5℃; for 3.16667h; Product distribution / selectivity;	85.84%

: 75-75-2
methanesulfonic acid

: 284461-73-0
sorafenib

: 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]-carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide mesylate

Conditions

Conditions	Yield
In ethanol at 26 - 78℃; for 11h; Product distribution / selectivity;	85.08%

Sorafenib Chemical Properties

Sorafenib is a drug approved for the treatment of primary kidney cancer , also for the treatment of advanced renal cell carcinoma, and advanced primary liver cancer (hepatocellular carcinoma).It's usually light yellow solid.

Molecular Formula: C₂₁H₁₆ClF₃N₄O₃
Molecular Weight: 464.83
Melting point: 202-204°C

Sorafenib Uses

Sorafenib is a potent RAF kinase inhibitor,and it is used an antineoplastic agent.

Sorafenib Safety Profile

Side effects:skin rash, hand-foot skin reactions, diarrhea, and hypertension. It has also been implicated in the development of reversible posterior leukoencephalopathy syndrome.

Product Name

Sorafenib tosylate

Synthetic route

Sorafenib Chemical Properties

Sorafenib Uses

Sorafenib Safety Profile

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