Pirfenidone supplier | CasNO.53179-13-8

Name
Pirfenidone
EINECS 621-260-7
CAS No. 53179-13-8
Article Data44
CAS DataBase
Density 1.138 g/cm³
Solubility DMSO: ≥10 mg/mL, soluble
Melting Point 96-97 °C
Formula C₁₂H₁₁NO
Boiling Point 329.075 °C at 760 mmHg
Molecular Weight 185.225
Flash Point 152.741 °C
Transport Information
Appearance Off-white solid
Safety 36
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
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-;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 13284-42-9
2-pentenenitrile

: 62-53-3
aniline

: 149-73-5
trimethyl orthoformate

: 53179-13-8
Pirfenidone

Conditions

Conditions	Yield
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%

...Expand

: C12H13NO2

: 53179-13-8
Pirfenidone

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide In methanol	92%

: 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

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

...Expand

: 1206801-33-3
5-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid

: 53179-13-8
Pirfenidone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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.

...Expand

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

: 13061-96-6
dihydroxy-methyl-borane

: 53179-13-8
Pirfenidone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
Stage #1: 2-chloro-5-methyl-1(((trifluoromethyl)sulfonyl)oxy)pyridine-1-ium trifluoromethanesulfonate; benzene With C10H8N2Ru(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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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;

...Expand

: 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

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

...Expand

: 1003-68-5
5-methyl-2-pyridone

: 591-50-4
iodobenzene

: 12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8
copper

: 53179-13-8
Pirfenidone

Conditions

Conditions	Yield
With potassium carbonate In benzene

...Expand

: 104-92-7
1-bromo-4-methoxy-benzene

: 13466-41-6
4-methyl-1H-pyridin-2-one

: 53179-13-8
Pirfenidone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sulfuric acid In acetone at 40 - 45℃;	99%

: 53179-13-8
Pirfenidone

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

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;	92%

: 53179-13-8
Pirfenidone

: C12H10(2)HNO

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Pirfenidone 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)	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: Harmful

Xn
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.

Product Name

Pirfenidone

Synthetic route

Pirfenidone Specification

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