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53179-13-8

Basic Information
CAS No.: 53179-13-8
Name: Pirfenidone
Molecular Structure:
Molecular Structure of 53179-13-8 (Pirfenidone)
Formula: C12H11NO
Molecular Weight: 185.22
Synonyms: 5-Methyl-1-phenyl-1H-pyridin-2-one;5-Methyl-1-phenyl-2(1H)-pyridinone;5-Methyl-1-phenyl-2(1H)-pyridone;AMR 69;Deskar;Pirespa;2(1H)-Pyridinone,5-methyl-1-phenyl-;
EINECS: 621-260-7
Density: 1.138 g/cm3
Melting Point: 96-97 °C
Boiling Point: 329.075 °C at 760 mmHg
Flash Point: 152.741 °C
Solubility: DMSO: ≥10 mg/mL, soluble
Appearance: Off-white solid
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
Transport Information:
PSA: 22.00000
LogP: 2.14590
Synthetic route
1003-68-5

5-methyl-2-pyridone

58109-40-3

diphenyliodonium hexafluorophosphate

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With triethylamine; copper(l) chloride In toluene at 20℃; for 0.5h; Inert atmosphere;99%
1003-68-5

5-methyl-2-pyridone

603-33-8

triphenylbismuthane

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With pyridine; copper diacetate In dichloromethane at 50℃; for 16h; Reagent/catalyst;98%

5-bromo-N-phenyl-(1H)-pyridin-2-one

potassium trifluoro(methyl)boranuide

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; ruphos In water; toluene at 87℃; Suzuki-Miyaura Coupling; Inert atmosphere;97%
13284-42-9

2-pentenenitrile

122-51-0

orthoformic acid triethyl ester

62-53-3

aniline

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Stage #1: 2-pentenenitrile; orthoformic acid triethyl ester With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100 - 105℃; for 4h;
Stage #2: aniline In N,N-dimethyl-formamide at 80 - 100℃; for 3h;
Stage #3: With water In N,N-dimethyl-formamide at 20℃; for 2h;
93.6%
13284-42-9

2-pentenenitrile

62-53-3

aniline

149-73-5

trimethyl orthoformate

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Stage #1: 2-pentenenitrile; trimethyl orthoformate With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 90 - 100℃; for 4h;
Stage #2: aniline In N,N-dimethyl-formamide at 80 - 95℃; for 3h;
Stage #3: With water In N,N-dimethyl-formamide at 20℃; for 2h; Reagent/catalyst; Temperature; Solvent;
92.7%

C12H13NO2

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With Trimethyl orthoacetate In ethanol at 25 - 80℃; for 8h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;92.5%

C12H11NO*H2O4S

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With sodium hydroxide In methanol92%
1003-68-5

5-methyl-2-pyridone

591-50-4

iodobenzene

A

51933-81-4

5-methyl-2-phenoxypyridine

B

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 8h; Reagent/catalyst; Temperature; Time; Solvent; Ullmann-Goldberg Substitution;A 4%
B 90%
1206801-33-3

5-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid

53179-13-8

Pirfenidone

Conditions
ConditionsYield
In dimethyl sulfoxide at 100℃; for 9h; Solvent; Temperature;88.6%

diphenyl(trifluoromethanesulfonato)-λ3-iodane

1003-68-5

5-methyl-2-pyridone

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With N,N-diethylaniline In fluorobenzene at 85℃; for 16h; Reagent/catalyst; chemoselective reaction;88%
1003-68-5

5-methyl-pyridin-2-ol

108-86-1

bromobenzene

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25 - 130℃; Temperature;87.5%

5-bromo-N-phenyl-(1H)-pyridin-2-one

74-88-4

methyl iodide

A

13131-02-7

1-phenyl-1H-pyridin-2-one

B

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Stage #1: 5-bromo-N-phenyl-(1H)-pyridin-2-one With TurboGrignard In tetrahydrofuran at -5 - 0℃;
Stage #2: methyl iodide In tetrahydrofuran at -5 - 0℃; for 1h;
A 87.2%
B 12.8%
With TurboGrignard In tetrahydrofuran at -5 - 20℃; for 1h; Inert atmosphere;A 87.2%Chromat.
B 12.8 %Chromat.

5-bromo-N-phenyl-(1H)-pyridin-2-one

13061-96-6

dihydroxy-methyl-borane

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; ruphos In water; toluene at 20 - 87℃; for 2h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;87%
1003-68-5

5-methyl-2-pyridone

diphenyliodonium tetrafluoroborate

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With triethylamine; copper(l) chloride In toluene at 20℃; for 5h; Inert atmosphere;86%
1003-68-5

5-methyl-2-pyridone

108-90-7

chlorobenzene

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine for 16h; Temperature; Reagent/catalyst; Inert atmosphere; Reflux;84%

2-chloro-5-methyl-1(((trifluoromethyl)sulfonyl)oxy)pyridine-1-ium trifluoromethanesulfonate

71-43-2

benzene

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Stage #1: 2-chloro-5-methyl-1(((trifluoromethyl)sulfonyl)oxy)pyridine-1-ium trifluoromethanesulfonate; benzene With C10H8N2*Ru(2+)*2F6P(1-) In acetonitrile at 23 - 25℃; for 12h; Sealed tube; Irradiation;
Stage #2: With water; sodium hydrogencarbonate In acetonitrile at 50℃; for 10h;
80%
108-86-1

bromobenzene

1003-68-5

5-methyl-2-pyridone

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Stage #1: 5-methyl-2-pyridone With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; for 1h; Large scale;
Stage #2: With copper In N,N-dimethyl-formamide at 70 - 80℃; for 1h; Large scale;
Stage #3: bromobenzene In N,N-dimethyl-formamide at 135 - 145℃; for 12h; Large scale;
78%
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide for 1h; Reflux;76%
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide for 1h; Reflux;76%
1003-68-5

5-methyl-2-pyridone

591-50-4

iodobenzene

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With copper; potassium carbonate In N,N-dimethyl-formamide at 160 - 170℃; for 20h; Ullmann Condensation;73%
1003-68-5

5-methyl-2-pyridone

98-80-6

phenylboronic acid

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With pyridine; copper(II) acetate monohydrate In dichloromethane for 24h; Chan-Lam Coupling;70%
With pyridine; copper(II) acetate monohydrate In dichloromethane at 20℃; for 24h; Chan-Lam Coupling; Molecular sieve;12%
1003-68-5

5-methyl-2-pyridone

66003-76-7

Diphenyliodonium triflate

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With triethylamine; copper(l) chloride In toluene at 20℃; for 0.5h; Inert atmosphere;70%
1003-68-5

5-methyl-pyridin-2-ol

591-50-4

iodobenzene

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With copper; potassium carbonate at 180℃; for 8h;67.9%
With potassium carbonate; copper at 180 - 190℃; for 7h;56%
With potassium carbonate; copper at 180 - 190℃; for 7h;56%
With potassium carbonate; copper(l) chloride In diethyl ether; acetone at 190℃; for 7h; Solvent;

diphenyl(trifluoromethanesulfonato)-λ3-iodane

1003-68-5

5-methyl-2-pyridone

A

51933-81-4

5-methyl-2-phenoxypyridine

B

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With caesium carbonate In 1,2-dichloro-ethane at 120℃;A 33%
B 42%

5-bromo-N-phenyl-(1H)-pyridin-2-one

74-88-4

methyl iodide

A

13131-02-7

1-phenyl-1H-pyridin-2-one

B

53179-13-8

Pirfenidone

C

1,1'-diphenyl-[3,3'-bipyridine]-6,6'(1H,1'H)-dione

Conditions
ConditionsYield
Stage #1: 5-bromo-N-phenyl-(1H)-pyridin-2-one With TurboGrignard In tetrahydrofuran at -12 - -10℃; Inert atmosphere;
Stage #2: methyl iodide With copper(I) cyanide lithium chloride In tetrahydrofuran at -12 - -10℃; for 20h; Inert atmosphere;
A 27.6%
B 40.8%
C 11.8%
With TurboGrignard; copper(I) cyanide di(lithium chloride) In tetrahydrofuran at -20 - -10℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;
108-86-1

bromobenzene

1003-68-5

5-methyl-2-pyridone

A

51933-81-4

5-methyl-2-phenoxypyridine

B

53179-13-8

Pirfenidone

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 2h; Ullmann-Goldberg Substitution;A 2%
B 39%
104-92-7

1-bromo-4-methoxy-benzene

13466-41-6

4-methyl-1H-pyridin-2-one

53179-13-8

Pirfenidone

Conditions
ConditionsYield
pyridine In dichloromethane at 0 - 20℃; for 2h;

1-Menthol

53179-13-8

Pirfenidone

1603-41-4

(5-methyl-pyridin-2-yl)amine

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 10 °C
2: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: sulfuric acid / 10 °C
1.2: 0.33 h / pH 7 - 8 / Reflux
2.1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; sodium nitrite / water / 10 °C / pH 7 - 8 / Reflux
2: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 1 h / Reflux
View Scheme
13472-85-0

2-methoxy-5-bromopyridine

53179-13-8

Pirfenidone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ruphos; palladium diacetate; potassium carbonate / toluene; water / 6 h / 87 °C / Inert atmosphere
1.2: 2 h / 0 - 5 °C
2.1: hydrogenchloride; potassium iodide / water / 3 h / 130 °C
3.1: copper(II) acetate monohydrate; pyridine / dichloromethane / 24 h
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tert-butyl methyl ether; hexane / 2 h / -50 °C / Inert atmosphere
1.2: 12.5 h / -50 - 20 °C / Inert atmosphere
1.3: 8 h / 5 °C
2.1: hydrogenchloride; potassium iodide / water / 3 h / 130 °C
3.1: copper(II) acetate monohydrate; pyridine / dichloromethane / 24 h
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 7 h / Reflux
2: copper(II) acetate monohydrate; pyridine / dichloromethane / 20 °C
3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,2-dimethoxyethane / 24 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 7 h / Reflux
2: copper(II) acetate monohydrate; pyridine / dichloromethane / 20 °C
3: ruphos; palladium diacetate; potassium carbonate / toluene; water / 2 h / 20 - 87 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 7 h / Reflux
2: copper(II) acetate monohydrate; pyridine / dichloromethane / 20 °C
3: ruphos; palladium diacetate; potassium carbonate / toluene; water / 87 °C / Inert atmosphere
View Scheme
53179-13-8

Pirfenidone

C12H11NO*H2O4S

Conditions
ConditionsYield
With sulfuric acid In acetone at 40 - 45℃;99%
53179-13-8

Pirfenidone

(RS)-5-methyl-1-phenylpiperidin-2-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;92%
53179-13-8

Pirfenidone

C12H10(2)HNO

Conditions
ConditionsYield
With tetrakis(tetrabutylammonium)decatungstate(VI); 2,4,6-Triisopropylthiophenol; water-d2; trifluoroacetic acid In acetonitrile Irradiation; regioselective reaction;85%
53179-13-8

Pirfenidone

1347692-68-5

5-bromomethyl-1-phenyl-1H-pyridine-2-one

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 4h; Reflux;61.7%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 4h; Reflux; Irradiation;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 2h;
719-98-2

2-((trifluoromethyl)thio)isoindoline-1,3-dione

53179-13-8

Pirfenidone

C13H10F3NOS

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium carbonate In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;51%
53179-13-8

Pirfenidone

677-25-8

ethylenesulfonyl fluoride

6-methyl-3-oxo-2-phenyl-2-azabicyclo[4.2.0]oct-4-ene-7-sulfonyl fluoride

Conditions
ConditionsYield
With thio-xanthene-9-one In acetonitrile at 20℃; for 24h; UV-irradiation; Inert atmosphere;48%
53179-13-8

Pirfenidone

81290-20-2

(trifluoromethyl)trimethylsilane

5-methyl-1-phenyl-3-(trifluoromethyl)pyridin-2(1H)-one

Conditions
ConditionsYield
With potassium fluoride; copper diacetate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 2h; Inert atmosphere; Sealed tube;44%
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    Pirfenidone

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    APIAppearance:White to white creamy crystalline powder

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    Pirfenidone High Purity Pharmaceutical Raw Material CAS 53179-13-8

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  • Pirfenidone  53179-13-8

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Specification

1. Introduction of Pirfenidone
Pirfenidone is a white to white creamy crystalline powder or off-white solid. The IUPAC Name of this chemical is 5-Methyl-1-phenylpyridin-2-one. Its Classification Code of Pirfenidone is Analgesic; Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory; Anti-inflammatory agents, non-steroidal; Antineoplastic agents; Antipyretic; Antirheumatic Agents; Central Nervous System Agents; Drug / Therapeutic Agent; Peripheral Nervous System Agents; Sensory System Agents. Pirfenidone belongs to Aromatics Compounds; Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Cytokine signaling. Pirfenidone can solube in water.

2. Properties of Pirfenidone
Physical properties about Pirfenidone are:
(1)Melting Point: 96-97°C; (2)H bond acceptors: 2; (3)Freely Rotating Bonds: 1; (4)Polar Surface Area: 20.31 Å2; (5)Index of Refraction: 1.592; (6)Molar Refractivity: 55.11 cm3; (7)Molar Volume: 162.7 cm3; (8)Surface Tension: 43.2 dyne/cm; (9)Density: 1.137 g/cm3; (10)Flash Point: 152.7 °C; (11)Enthalpy of Vaporization: 57.15 kJ/mol; (12)Boiling Point: 329.1 °C at 760 mmHg; (13)Vapour Pressure: 0.000182 mmHg at 25°C; (14)XLogP3-AA: 1.9; (15)H-Bond Donor: 0; (16)H-Bond Acceptor: 1; (17)Rotatable Bond Count: 1; (18)Exact Mass: 185.084064; (19)MonoIsotopic Mass: 185.084064; (20)Topological Polar Surface Area: 20.3; (21)Heavy Atom Count: 14; (22)Formal Charge: 0; (23)Complexity: 285; (24)Isotope Atom Count: 0; (25)Defined Atom Stereocenter Count: 0; (26)Undefined Atom Stereocenter Count: 0; (27)Defined Bond Stereocenter Count: 0; (28)Undefined Bond Stereocenter Count: 0; (29)Covalently-Bonded Unit Count: 1; (30)Feature 3D Acceptor Count: 1; (31)Feature 3D Ring Count: 2; (32)Effective Rotor Count: 1; (33)Conformer Sampling RMSD: 0.4.

3. Structure Descriptors of Pirfenidone
(1)InChI: InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
(2)InChIKey: ISWRGOKTTBVCFA-UHFFFAOYSA-N
(3)Canonical SMILES: CC1=CN(C(=O)C=C1)C2=CC=CC=C2
(4)Smiles: n1(c2ccccc2)c(ccc(c1)C)=O

4. Toxicity of Pirfenidone

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 40mg/kg (40mg/kg)   European Patent Application. Vol. #383591,
cat LD50 oral 500mg/kg (500mg/kg)   European Patent Application. Vol. #383591,
dog LD50 intravenous 200mg/kg (200mg/kg)   European Patent Application. Vol. #383591,
dog LD50 oral 300mg/kg (300mg/kg)   European Patent Application. Vol. #383591,
guinea pig LD50 intraperitoneal 460mg/kg (460mg/kg)   European Patent Application. Vol. #383591,
guinea pig LD50 oral 810mg/kg (810mg/kg)   European Patent Application. Vol. #383591,
monkey LD50 intravenous 100mg/kg (100mg/kg)   European Patent Application. Vol. #383591,
mouse LD50 intraperitoneal 420mg/kg (420mg/kg)   United States Patent Document. Vol. #3974281,
mouse LD50 intravenous 285mg/kg (285mg/kg)   European Patent Application. Vol. #383591,
mouse LD50 oral 580mg/kg (580mg/kg)   United States Patent Document. Vol. #4042699,
rabbit LD50 intravenous 280mg/kg (280mg/kg)   European Patent Application. Vol. #383591,
rat LD50 intraperitoneal 430mg/kg (430mg/kg)   European Patent Application. Vol. #383591,
rat LD50 oral 1295mg/kg (1295mg/kg)   European Patent Application. Vol. #383591,

5. Safety information of Pirfenidone
Hazard Codes: HarmfulXn
Risk Statements: 22 
R22: Harmful if swallowed.
Safety Statements: 36 
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: UV1148200

6. Uses of Pirfenidone
Pirfenidone is used in multiple fibrotic conditions, including those of the lung, kidney and liver. Pirfenidone has well-established antifibrotic and anti-inflammatory properties in various in vitro systems and animal models of fibrosis.

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