Product Name

  • Name

    Ataluren (PTC124)

  • EINECS
  • CAS No. 775304-57-9
  • Article Data14
  • CAS DataBase
  • Density 1.379 g/cm3
  • Solubility
  • Melting Point
  • Formula C15H9FN2O3
  • Boiling Point 503.7 °C at 760 mmHg
  • Molecular Weight 284.246
  • Flash Point 258.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 775304-57-9 (Ataluren (PTC124))
  • Hazard Symbols
  • Synonyms Ataluren;PTC 124;
  • PSA 76.22000
  • LogP 3.24090

Synthetic route

3-((5-(2-fluorophenyl))-(1,2,4-oxadiazol-3-yl))benzoic acid methyl ester
775304-60-4

3-((5-(2-fluorophenyl))-(1,2,4-oxadiazol-3-yl))benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 3-((5-(2-fluorophenyl))-(1,2,4-oxadiazol-3-yl))benzoic acid methyl ester With sodium hydroxide; water at 100℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water		96%
Stage #1: 3-((5-(2-fluorophenyl))-(1,2,4-oxadiazol-3-yl))benzoic acid methyl ester With sodium hydroxide; water In tetrahydrofuran at 100℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water		96%
Stage #1: 3-((5-(2-fluorophenyl))-(1,2,4-oxadiazol-3-yl))benzoic acid methyl ester With sodium hydroxide; water In tetrahydrofuran at 100℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water		96%

Conditions
ConditionsYield
Stage #1: 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde With potassium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 20 - 30℃;
Stage #2: With sodium chlorite In water; acetonitrile at 0 - 30℃; for 5h;		90%

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
In tert-butyl alcohol at 80℃; for 24h;88.4%
5-(2-fluorophenyl)-3-(3-methylphenyl)-1,2,4-oxadiazole
692771-01-0

5-(2-fluorophenyl)-3-(3-methylphenyl)-1,2,4-oxadiazole

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
With basic cobalt(II) carbonate; sodium bromide In acetic acid at 95℃; for 11h; Green chemistry;85%
With pyridine; potassium permanganate In water at 85℃; for 6.5h;40%
2-Fluorobenzoyl chloride
393-52-2

2-Fluorobenzoyl chloride

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Stage #1: 3-Cyanobenzoic acid With hydroxylamine In water; tert-butyl alcohol at 38 - 41℃; for 21h;
Stage #2: 2-Fluorobenzoyl chloride With triethylamine In water; tert-butyl alcohol at 27 - 40℃; for 7h;
Stage #3: With hydrogenchloride; water Product distribution / selectivity; more than 3 stages;		76%
3-(N'-hydroxycarbamimidoyl)benzoic acid
199447-10-4

3-(N'-hydroxycarbamimidoyl)benzoic acid

o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
With tetrachloromethane; diethoxymethylsilane; Bis(p-nitrophenyl) phosphate; triphenylphosphine In toluene at 120℃; for 24h; Reflux; Large scale;65%
3-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester
1141475-82-2, 1227154-43-9, 775304-79-5

3-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester

2-Fluorobenzoyl chloride
393-52-2

2-Fluorobenzoyl chloride

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / 1,4-dioxane / 12.5 h / 0 °C / Reflux
2: sodium hydroxide; water / ethanol / 3 h / 20 °C
View Scheme
C15H13FN2O

C15H13FN2O

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; acetic acid / 3.5 h / 80 °C
2: pyridine; potassium permanganate / water / 6.5 h / 85 °C
View Scheme
o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C
2: hydroxylamine hydrochloride; acetic acid / 3.5 h / 80 °C
3: pyridine; potassium permanganate / water / 6.5 h / 85 °C
View Scheme
3-methylbenzenecarboximidamide hydrochloride
20680-59-5

3-methylbenzenecarboximidamide hydrochloride

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C
2: hydroxylamine hydrochloride; acetic acid / 3.5 h / 80 °C
3: pyridine; potassium permanganate / water / 6.5 h / 85 °C
View Scheme
3-Cyanobenzoic acid
1877-72-1

3-Cyanobenzoic acid

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 4.33 h / 20 °C
2.1: hydroxylamine / ethanol; water / 1 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.33 h / 20 °C
4.1: toluene / 22 h / 5 - 130 °C / Dean-Stark
5.1: sodium hydroxide; water / tetrahydrofuran / 2 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate; hydroxylamine hydrochloride / water; ethanol / 3 h / Reflux
2.1: potassium carbonate / water; toluene / 0.08 h / 20 - 30 °C
2.2: 1 h / 0 - 10 °C
3.1: tert-butyl alcohol / 24 h / 80 °C
View Scheme
methyl 3-cyanobenzoate
13531-48-1

methyl 3-cyanobenzoate

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydroxylamine / ethanol; water / 1 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.33 h / 20 °C
3: toluene / 22 h / 5 - 130 °C / Dean-Stark
4: sodium hydroxide; water / tetrahydrofuran / 2 h / 100 °C
View Scheme
Multi-step reaction with 4 steps
1: hydroxylamine / ethanol; water / 20 °C / Reflux
2: trifluoroacetic acid / 0.58 h / 20 - 60 °C
3: palladium diacetate; triphenylphosphine; silver(I) acetate / toluene / 0.5 h / 150 °C / Microwave irradiation; Sealed tube
4: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydroxylamine / ethanol; water / 1 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.33 h / 5 - 20 °C
3: toluene / 22 h / 5 - 130 °C / Dean-Stark apparatus
4: sodium hydroxide; water / tetrahydrofuran / 2 h / 100 °C
View Scheme
Multi-step reaction with 4 steps
1: hydroxylamine hydrochloride; sodium ethanolate / ethanol / 20 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 5 - 20 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C
4: lithium hydroxide / tetrahydrofuran; water / 24 h / 20 °C
View Scheme
3-(carbamimidoyl)benzoic acid methyl ester
15676-11-6

3-(carbamimidoyl)benzoic acid methyl ester

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.33 h / 20 °C
2: toluene / 22 h / 5 - 130 °C / Dean-Stark
3: sodium hydroxide; water / tetrahydrofuran / 2 h / 100 °C
View Scheme
methyl 3-(1,2,4-oxadiazol-3-yl)benzoate

methyl 3-(1,2,4-oxadiazol-3-yl)benzoate

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium diacetate; triphenylphosphine; silver(I) acetate / toluene / 0.5 h / 150 °C / Microwave irradiation; Sealed tube
2: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / 20 °C
View Scheme
3-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester
1141475-82-2, 1227154-43-9, 775304-79-5

3-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / 0.58 h / 20 - 60 °C
2: palladium diacetate; triphenylphosphine; silver(I) acetate / toluene / 0.5 h / 150 °C / Microwave irradiation; Sealed tube
3: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.33 h / 5 - 20 °C
2: toluene / 22 h / 5 - 130 °C / Dean-Stark apparatus
3: sodium hydroxide; water / tetrahydrofuran / 2 h / 100 °C
View Scheme
3-cyanobenzaldehyde dimethyl acetal

3-cyanobenzaldehyde dimethyl acetal

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydroxylamine / water; methanol / 2.5 h / 50 °C
2.1: sodium hydrogencarbonate / water / 0.08 h / 20 - 30 °C
2.2: 1 h / 20 - 30 °C
3.1: toluene / 18 h / 85 °C
4.1: potassium dihydrogenphosphate; dihydrogen peroxide / water; acetonitrile / 20 - 30 °C
4.2: 5 h / 0 - 30 °C
View Scheme
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 3.08 h / 20 - 45 °C
2.1: hydroxylamine / water; methanol / 2.5 h / 50 °C
3.1: sodium hydrogencarbonate / water / 0.08 h / 20 - 30 °C
3.2: 1 h / 20 - 30 °C
4.1: toluene / 18 h / 85 °C
5.1: potassium dihydrogenphosphate; dihydrogen peroxide / water; acetonitrile / 20 - 30 °C
5.2: 5 h / 0 - 30 °C
View Scheme
3-(dimethoxymethyl)-N'-hydroxybenzimidamide

3-(dimethoxymethyl)-N'-hydroxybenzimidamide

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydrogencarbonate / water / 0.08 h / 20 - 30 °C
1.2: 1 h / 20 - 30 °C
2.1: toluene / 18 h / 85 °C
3.1: potassium dihydrogenphosphate; dihydrogen peroxide / water; acetonitrile / 20 - 30 °C
3.2: 5 h / 0 - 30 °C
View Scheme
N'-((2-fluorobenzoyl)oxy)-3-formylbenzimidamide

N'-((2-fluorobenzoyl)oxy)-3-formylbenzimidamide

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene / 18 h / 85 °C
2.1: potassium dihydrogenphosphate; dihydrogen peroxide / water; acetonitrile / 20 - 30 °C
2.2: 5 h / 0 - 30 °C
View Scheme
3-(N-2-fluorobenzoylcarbamimidoyl)-benzoic acid methyl ester
775304-80-8

3-(N-2-fluorobenzoylcarbamimidoyl)-benzoic acid methyl ester

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / 22 h / 5 - 130 °C / Dean-Stark apparatus
2: sodium hydroxide; water / tetrahydrofuran / 2 h / 100 °C
View Scheme
3-(N-hydroxyamidino)benzoic acid methyl ester
1141475-82-2, 1227154-43-9, 775304-79-5

3-(N-hydroxyamidino)benzoic acid methyl ester

ataluren
775304-57-9

ataluren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 5 - 20 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C
3: lithium hydroxide / tetrahydrofuran; water / 24 h / 20 °C
View Scheme
ataluren
775304-57-9

ataluren

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid sodium salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid sodium salt

Conditions
ConditionsYield
With sodium hydroxide; water at 100℃; for 2h; Heating / reflux;96%
With sodium hydroxide In ethanol; water
ataluren
775304-57-9

ataluren

5-(2-fluorophenyl)-3-(3-fluorophenyl)-1,2,4-oxadiazole

5-(2-fluorophenyl)-3-(3-fluorophenyl)-1,2,4-oxadiazole

Conditions
ConditionsYield
Stage #1: ataluren With tetrakis(acetonitrile)copper(I)tetrafluoroborate; tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 23℃; for 0.5h; Sealed tube; Inert atmosphere;
Stage #2: In acetonitrile at 35℃; for 24h; Irradiation; Sealed tube; Inert atmosphere;		45%
ataluren
775304-57-9

ataluren

2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline
3416-93-1

2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline

N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)benzamide

N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)benzamide

Conditions
ConditionsYield
Stage #1: ataluren With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #3: 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline In dichloromethane at 20℃; for 72h; Inert atmosphere;		25%
ataluren
775304-57-9

ataluren

ATP
56-65-5

ATP

PTC124-AMP
1227154-38-2

PTC124-AMP

Conditions
ConditionsYield
With Photinus pyralis luciferase aq. buffer; Enzymatic reaction;
ataluren
775304-57-9

ataluren

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid magnesium salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid magnesium salt

Conditions
ConditionsYield
With magnesium methanolate In methanol; dichloromethane Reagent/catalyst; Solvent;
ataluren
775304-57-9

ataluren

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid potassium salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid potassium salt

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water
ataluren
775304-57-9

ataluren

2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid tromethamine salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid tromethamine salt

Conditions
ConditionsYield
In methanol; acetone Solvent;
ataluren
775304-57-9

ataluren

L-lysine
56-87-1

L-lysine

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid L-lysine salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid L-lysine salt

Conditions
ConditionsYield
In tetrahydrofuran; water
ataluren
775304-57-9

ataluren

L-arginine
74-79-3

L-arginine

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid L-arginine salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid L-arginine salt

Conditions
ConditionsYield
In ethanol; water Sonication;
ataluren
775304-57-9

ataluren

L-histidine
71-00-1

L-histidine

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid L-histidine salt

3-[5-(2-fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid L-histidine salt

Conditions
ConditionsYield
In ethanol; water Solvent; Sonication;

Ataluren Specification

The Ataluren with the CAS number 775304-57-9 is also called Benzoic acid,3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-. Its molecular formula is C15H9FN2O3. This chemical is a kind of organics. It should be stored in dry and cool environment.

The properties of the chemical are: (1)ACD/LogP: 3.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 0.66; (5)ACD/BCF (pH 5.5): 5.07; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 32.08; (8)ACD/KOC (pH 7.4): 2.19; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 65.22 Å2; (13)Index of Refraction: 1.603; (14)Molar Refractivity: 70.84 cm3; (15)Molar Volume: 205.9 cm3; (16)Polarizability: 28.08×10-24cm3; (17)Surface Tension: 56.8 dyne/cm; (18)Enthalpy of Vaporization: 81.4 kJ/mol; (19)Vapour Pressure: 5.75×10-11 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc3ccccc3c1nc(no1)c2cc(ccc2)C(=O)O
(2)InChI: InChI=1/C15H9FN2O3/c16-12-7-2-1-6-11(12)14-17-13(18-21-14)9-4-3-5-10(8-9)15(19)20/h1-8H,(H,19,20)
(3)InChIKey: OOUGLTULBSNHNF-UHFFFAOYAJ

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