133238-87-6

Basic information

• Product Name: 2-Butyl-5-nitrobenzofuran
• Synonyms: 2-Butyl-5-nitrobenzofuran;Benzofuran, 2-butyl-5-nitro-;2-butyl-5-nitro-1-benzofuran;2-n-Butyl-5-nitrobenzofuran;5-nitro-2-butyl benzofuran;2-Butyl-5-NIitrobenzofuran
• CAS NO: 133238-87-6
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• EINECS: 1806241-263-5
• Product Categories: API;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 133238-87-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 329.721 °C at 760 mmHg
• Flash Point: 153.21 °C
• Appearance: Pale yellow to yellow liquid
• Density: 1.191
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-Butyl-5-nitrobenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butyl-5-nitrobenzofuran(133238-87-6)
• EPA Substance Registry System: 2-Butyl-5-nitrobenzofuran(133238-87-6)

Safety Data

• Hazardous Substances Data: 133238-87-6(Hazardous Substances Data)

Usage

Chemical Properties

Bright Yellow Low Melting Solid

Uses

Dronedarone intermediate.

InChI:InChI=1/C12H13NO3/c1-2-3-4-11-8-9-7-10(13(14)15)5-6-12(9)16-11/h5-8H,2-4H2,1H3

Synthetic route

Koshlands reagent I (772-33-8) + n-valeryl chloride (638-29-9) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Stage #1: Koshlands reagent I With triphenylphosphine In dichloromethane for 1h; Reflux; Stage #2: n-valeryl chloride With triethylamine In dichloromethane for 3h; Reflux;	94%

2-butyl-5-nitro-2,3-dihydrobenzofuran-3-ol → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
With sulfuric acid In ethanol for 4h; Heating / reflux;	80%
With hydrogenchloride In methanol; water at 90 - 95℃; for 5h;	7.6 g

2-(hex-2-en-1-yl)-4-nitrophenol (1068753-61-6) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
With sodium carbonate; p-benzoquinone; bis(benzonitrile)palladium(II) dichloride In 1,4-dioxane at 80℃; for 3h;	50%

2-(2-formyl-4-nitrophenoxy)hexanoic acid (335153-21-4) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
With sodium acetate; acetic anhydride; acetic acid for 3h; Heating;

methyl 2-bromohexanoate (5445-19-2) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C 2: 80 percent / NaOH / Heating 3: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme

5-Nitrosalicylaldehyde (97-51-8) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C 2: 80 percent / NaOH / Heating 3: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme

methyl 2-(2-formyl-4-nitrophenoxy)butanoate (847869-79-8) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOH / 0.5 h / 90 °C 2: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C 3: 80 percent / NaOH / Heating 4: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme

methyl 2-(2-formyl-4-nitrophenoxy)pentanoate (847869-80-1) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOH / 2 h / 50 °C 2: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C 3: 80 percent / NaOH / Heating 4: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme

methyl 2-(2-formyl-4-nitrophenoxy)hexanoate (335153-23-6) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / NaOH / Heating 2: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating View Scheme

4-nitro-phenol (100-02-7) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 2: aluminum (III) chloride / nitrobenzene / 5 h / 140 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 4: bromine / dichloromethane / 1 h / 25 - 30 °C 5: aluminum (III) chloride / dichloromethane / 15 - 20 °C 6: triethylamine / dichloromethane / 2 h / 25 - 30 °C 7: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 8: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 38 h / 40 - 55 °C / Large scale 2: 1,2-dichloro-ethane / 65 - 75 °C / Large scale 3: sodium hydrogencarbonate / 1,2-dichloro-ethane / 55 - 60 °C / Large scale View Scheme

2-butyl-5-nitrobenzofuran-3(2H)-one → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 2: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

p-nitrophenyl hexanoate (956-75-2) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: aluminum (III) chloride / nitrobenzene / 5 h / 140 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 3: bromine / dichloromethane / 1 h / 25 - 30 °C 4: aluminum (III) chloride / dichloromethane / 15 - 20 °C 5: triethylamine / dichloromethane / 2 h / 25 - 30 °C 6: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 7: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1-(2-hydroxy-5-nitrophenyl)hexan-1-one (1393093-65-6) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 2: bromine / dichloromethane / 1 h / 25 - 30 °C 3: aluminum (III) chloride / dichloromethane / 15 - 20 °C 4: triethylamine / dichloromethane / 2 h / 25 - 30 °C 5: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 6: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

1-(2-methoxy-5-nitrophenyl)hexan-1-one (1393093-66-7) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: bromine / dichloromethane / 1 h / 25 - 30 °C 2: aluminum (III) chloride / dichloromethane / 15 - 20 °C 3: triethylamine / dichloromethane / 2 h / 25 - 30 °C 4: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 5: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

2-bromo-1-(2-methoxy-5-nitrophenyl)hexan-1-one (1393093-67-8) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: aluminum (III) chloride / dichloromethane / 15 - 20 °C 2: triethylamine / dichloromethane / 2 h / 25 - 30 °C 3: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 4: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

2-bromo-1-(2-hydroxy-5-nitrophenyl)hexan-1-one (1393093-68-9) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 25 - 30 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 3: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

Hexanoyl chloride (142-61-0) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions

Yield

Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 2: aluminum (III) chloride / nitrobenzene / 5 h / 140 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C 4: bromine / dichloromethane / 1 h / 25 - 30 °C 5: aluminum (III) chloride / dichloromethane / 15 - 20 °C 6: triethylamine / dichloromethane / 2 h / 25 - 30 °C 7: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C 8: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C View Scheme

2-hydroxy-5-nitrobenzyl chloride (2973-19-5) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 65 - 75 °C / Large scale 2: sodium hydrogencarbonate / 1,2-dichloro-ethane / 55 - 60 °C / Large scale View Scheme

(2-hydroxy-5-nitrobenzyl)triphenylphosphine chloride (70726-17-9) + n-valeryl chloride (638-29-9) → 2-(n-butyl)-5-nitrobenzofuran (133238-87-6)

Conditions	Yield
With sodium hydrogencarbonate In 1,2-dichloro-ethane at 55 - 60℃; Large scale;

2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 5-amino 2-n-butyl benzofuran (141645-51-4)

Conditions	Yield
With ammonium formate; platinum(IV) oxide In ethanol at 20℃; under 18751.9 Torr;	99.2%
With ammonium formate; 5%-palladium/activated carbon In ethanol at 50℃; for 5h;
In ethanol

4-[3-(di-n-butylamino)-propoxy]-benzoic acid chloride hydrochloride + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-butyl-3-(4-[3(dibutylamino)propoxy]benzoyl)-5-nitro-benzofuran hydrochloride (437651-47-3)

Conditions	Yield
Stage #1: 4-[3-(di-n-butylamino)-propoxy]-benzoic acid chloride hydrochloride; 2-(n-butyl)-5-nitrobenzofuran In water at 0 - 22℃; for 1.5h; Stage #2: With iron(III) chloride at 20 - 22℃; for 1.5h;	98%
With iron(III) chloride In water at 0 - 22℃;	95%

4-methoxy-benzoyl chloride (100-07-2) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → (2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone (141627-42-1)

Conditions	Yield
Stage #1: 4-methoxy-benzoyl chloride; 2-(n-butyl)-5-nitrobenzofuran; aluminum (III) chloride In chlorobenzene at 25℃; for 2h; Reflux; Stage #2: With water In chlorobenzene Product distribution / selectivity;	90%
With aluminum (III) chloride In dichloromethane at 25℃; for 4h;	88%
With tin(IV) chloride In ice-water; 1,1-dichloroethane	83.5%

4-hydroxybenzoyl chloride (28141-24-4) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran (141645-16-1)

Conditions	Yield
With tin(IV) chloride In dichloromethane at 0 - 20℃; for 2.5h; Friedel-Crafts Acylation;	88%

phenylacetic acid (103-82-2) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-benzofuranyl phenyl ketone

Conditions	Yield
Stage #1: phenylacetic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 4h; Stage #2: With ethanol In chlorobenzene at 0℃;	86.8%

propionic acid (802294-64-0) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-benzofuranyl ethyl ketone

Conditions	Yield
Stage #1: propionic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 5h; Stage #2: With ethanol In chlorobenzene at 0℃;	84.3%

isobutyric Acid (79-31-2) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-benzofuranyl isobutyryl ketone

Conditions	Yield
Stage #1: isobutyric Acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 2h; Stage #2: With ethanol In chlorobenzene at 0℃;	84%

2-Methoxybenzoic acid (579-75-9) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-3-(2'-methoxy)-acetophenonebenzofuran (856758-04-8)

Conditions	Yield
Stage #1: 2-Methoxybenzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 22h; Stage #2: With ethanol In chlorobenzene at 0℃;	83.7%

p-Toluic acid (99-94-5) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-3-(4'-methyl)acetophenonebenzofuran

Conditions	Yield
Stage #1: p-Toluic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 5h; Stage #2: With ethanol In chlorobenzene at 0℃;	83.4%

4-hydroxy-benzoic acid (99-96-7) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran (141645-16-1)

Conditions	Yield
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 3.45 - 5h; Stage #2: With ethanol In chlorobenzene at 0 - 30℃; for 0.45 - 0.5h; Product distribution / selectivity;	81.6%
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With dimethylsilicon dichloride; iron(II) chloride In chlorobenzene at 23 - 50℃; for 5h; Stage #2: With ethanol In chlorobenzene at 20℃; Product distribution / selectivity;	76%
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With tetrachlorosilane; iron(III) chloride In chlorobenzene at 23 - 50℃; for 5h; Stage #2: With ethanol In chlorobenzene at 20℃; Product distribution / selectivity;	75%
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; bismuth(lll) trifluoromethanesulfonate In chlorobenzene at 23 - 60℃; for 15h; Stage #2: With ethanol In chlorobenzene at 20℃; Product distribution / selectivity;	10%
With trichlorophosphate; zinc(II) chloride at 23 - 60℃; for 15h; Product distribution / selectivity;	1%

benzoic acid (65-85-0) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-butyl-3-(benzoyl)-5-nitrobenzofuran

Conditions	Yield
Stage #1: benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 4h; Stage #2: With ethanol In chlorobenzene at 0℃;	81.3%

4-methoxyphenylboronic acid (5720-07-0) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → N-(2-butylbenzofuran-5-yl)-4-methoxybenzenesulfonamide

Conditions	Yield
With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	78%
With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere;	78%

acetic acid (64-19-7) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-benzofuranyl methyl ketone

Conditions	Yield
Stage #1: acetic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 5h; Stage #2: With ethanol In chlorobenzene at 0℃;	77.1%

carbon dioxide (124-38-9) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → N-(2-butylbenzofuran-5-yl)formamide

Conditions	Yield
With 1,1,3,3-Tetramethyldisiloxane; iron; potassium iodide In N,N-dimethyl-formamide at 135℃; for 28h; Schlenk technique; Sealed tube;	75%

4-methoxybenzoic acid (100-09-4) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → (2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone (141627-42-1)

Conditions	Yield
Stage #1: 4-methoxybenzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 4h; Stage #2: With ethanol In chlorobenzene at 0℃;	72.7%

naphthalene-2-boronic acid (32316-92-0) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → N-(2-butylbenzofuran-5-yl)naphthalene-2-sulfonamide

Conditions	Yield
With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	72%
With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere;	72%

para-chlorobenzoic acid (74-11-3) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-3-(4'-chloro)acetophenonebenzofuran

Conditions	Yield
Stage #1: para-chlorobenzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 120h; Stage #2: With ethanol In chlorobenzene at 0℃;	71.7%

carbon monoxide (201230-82-2) + 4-methylphenylboronic acid (5720-05-8) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → N-(2-butylbenzofuran-5-yl)-4-methylbenzamide

Conditions	Yield
With chloro-trimethyl-silane; nickel; triphenylphosphine; sodium iodide In N,N-dimethyl acetamide at 135℃; for 16h; Schlenk technique; Sealed tube;	69%

diethyl ether (60-29-7) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-Butyl 3-(4-hydroxy benzenesulfonyl) 5-nitro benzofuran

Conditions	Yield
With hydrogenchloride; sodium hydroxide; aluminium chloride; sodium sulfate In 1,1-dichloroethane; water	68%

3-Methoxybenzoic acid (586-38-9) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-3-(3'-methoxy)acetophenonebenzofuran

Conditions	Yield
Stage #1: 3-Methoxybenzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 5h; Stage #2: With ethanol In chlorobenzene at 0℃;	57.6%

3-tert-butyl-4-[3-(di-n-butylamino)propoxy]benzoyl chloride + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-butyl-3-[3-tert-butyl-4-[3-(di-n-butylamino)propoxy]benzoyl]-5-nitrobenzofuran

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 17h;	54%

4-(3-chloro propionamido)benzoyl chloride (141645-43-4) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 3-[4-(3-chloro propionamido)benzoyl] 2-n-butyl 5-nitro benzofuran (141645-45-6)

Conditions	Yield
With hydrogenchloride; aluminium chloride In calcium chloride; 1,2-dichloro-ethane; toluene	53%

4-trifluoromethylbenzoic acid (455-24-3) + 2-(n-butyl)-5-nitrobenzofuran (133238-87-6) → 2-n-butyl-5-nitro-3-(4'-trifluoromethyl)acetophenonebenzofuran

Conditions	Yield
Stage #1: 4-trifluoromethylbenzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 24h; Stage #2: With ethanol In chlorobenzene at 0℃;	34.5%

Upstream product

• 1068753-61-6 2-(hex-2-en-1-yl)-4-nitrophenol 
• 70726-17-9 (2-hydroxy-5-nitrobenzyl)triphenylphosphine chloride 
• 638-29-9 n-valeryl chloride 
• 2973-19-5 2-hydroxy-5-nitrobenzyl chloride 
• 772-33-8 Koshlands reagent I 
• 142-61-0 Hexanoyl chloride 
• 1393093-68-9 2-bromo-1-(2-hydroxy-5-nitrophenyl)hexan-1-one 
• 1393093-67-8 2-bromo-1-(2-methoxy-5-nitrophenyl)hexan-1-one 
• 1393093-66-7 1-(2-methoxy-5-nitrophenyl)hexan-1-one 
• 1393093-65-6 1-(2-hydroxy-5-nitrophenyl)hexan-1-one 
• 956-75-2 p-nitrophenyl hexanoate 
• 100-02-7 4-nitro-phenol 
• 335153-23-6 methyl 2-(2-formyl-4-nitrophenoxy)hexanoate 
• 847869-80-1 methyl 2-(2-formyl-4-nitrophenoxy)pentanoate 

Downstream Products

• 1448297-17-3 4-[(2-butyl-5-nitro-1-benzofuran-3-yl)carbonyl]phenyltrifluoromethanesulfonate 
• 141645-16-1 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran 
• 1278585-69-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)acetamide 
• 141626-57-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)-benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide 
• 141626-36-0 dronedarone 
• 500791-70-8 5-amino-2-n-butyl-3-[4-(3-di-n-butylamino propoxy)benzoyl]benzofuran bisoxalate 
• 1354567-97-7 N-[2-butyl-3-[4-(3-(di-n-butylamino)propoxy)benzoyl]-5-benzofuranyl]methanesulfonamide hydrobromide 

Relevant articles and documents

Discovery of dronedarone and its analogues as NLRP3 inflammasome inhibitors with potent anti-inflammation activity

Inhibiting NLRP3 inflammasome activation is a prospective therapeutic strategy for uncontrolled inflammatory diseases. It is the first time that dronedarone, a multiply ion channel blocker, was identified as a NLRP3-inflammasome inhibitor with an IC50 value of 6.84 μM against IL-1β release. A series of novel 5-amide benzofuran derivatives were designed and synthesized as NLRP3-inflammasome inhibitors. Compound 8c showed slightly increased activity (IC50 = 3.85 μM) against IL-1β release. Notably, treatment with 8c could significantly inhibit NLRP3-mediated IL-1β release and ameliorate peritoneal inflammation in a mouse model of sepsis. Collectively, 8c is a promising lead compound for further chemical development as a NLRP3 inhibitor with anti-inflammation effects.

Preparation method of key intermediate of dronedarone

The invention relates to a preparation method of a key intermediate of drug dronedarone for treating atrial fibrillation, and specifically relates to the 2-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran. According to the method provided by the invention, a series of reactions are performed by using inexpensive p-nitrophenol as a starting material to prepare the 2-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran, the process is smooth, the costs are lower, the yield is higher, the controllability is stronger, and the method is suitable for industrial production.

An alternative approach to synthesis of 2-n-butyl-5-nitrobenzofuran derivative: A key starting material for dronedarone hydrochloride

A practical synthesis of (2-butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl) methanone, a key intermediate in the preparation of anti arrhythmic drug, is described. The commercially available 4-nitrophenol (3) is converted in five steps to 2-butyl-5-nitrobenzofuran (9) which upon Friedel-Crafts acylation with 4-methoxybenzoyl chloride followed by deprotection of methyl group gives (2). Indian Academy of Sciences.