4265-27-4

Basic information

• Product Name: 2-Butylbenzofuran
• Synonyms: 2-BUTYLBENZOFURAN;2-N-BUTYLBENZO[B]FURAN;2-N-BUTYLBENZOFURAN;2-butyl-benzofura;2-Buthylbenzo【b】furan;2-Butylbenzofurane;2-Butyl;Butylbenzofurane
• CAS NO: 4265-27-4
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• EINECS: 224-250-7
• Mol File: 4265-27-4.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 114-116°C 8mm
• Flash Point: 101°C
• Appearance: /
• Density: 0,987 g/cm3
• Vapor Pressure: 0.039mmHg at 25°C
• Refractive Index: 1.5330
• BRN: 1365111
• CAS DataBase Reference: 2-Butylbenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butylbenzofuran(4265-27-4)
• EPA Substance Registry System: 2-Butylbenzofuran(4265-27-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 4265-27-4(Hazardous Substances Data)

Usage

Uses

2-Butylbenzofuran is used in process for prepn. of Amiodarone key intermediate 2-butyl-3-(3,5-diiodo-4-hydroxybenzoyl)benzofuran.

InChI:InChI=1/C12H14O/c1-2-3-7-11-9-10-6-4-5-8-12(10)13-11/h4-6,8-9H,2-3,7H2,1H3

Synthetic route

1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol (1248340-86-4) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With butyl magnesium bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h;	100%

2-(hex-1-yn-1-yl)phenol (125345-27-9) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
Stage #1: 2-(hex-1-yn-1-yl)phenol With N,N,N,N,-tetramethylethylenediamine; diethylzinc In toluene at 120℃; for 1h; Stage #2: With ammonium chloride In toluene	99%
Stage #1: 2-(hex-1-yn-1-yl)phenol With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 30h; Stage #2: With zinc(II) chloride In toluene at 120℃; for 1h; Stage #3: With ammonium chloride In water; toluene	98%
With caesium carbonate; copper(l) chloride In acetonitrile at 20℃; under 760.051 Torr; for 6h;	91.8%

2-Iodophenol (533-58-4) + hex-1-yne (693-02-7) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With copper(l) iodide; tetra-(n-butyl)ammonium iodide; potassium carbonate; palladium In toluene at 40℃; Reagent/catalyst; Temperature; Sonogashira Cross-Coupling; Inert atmosphere;	96.6%
With potassium carbonate at 60℃; for 1h;	91%
With copper(l) iodide; L-proline; sodium hydroxide In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; Sealed tube;	85%

2-phenoxyhexanal (158745-55-2) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With Amberlyst 15 In benzene Heating;	94%
With acetic acid; zinc(II) chloride for 0.166667h; Heating;	24%

n-butyl magnesium bromide (693-03-8) + 2-(methylsulfanyl)benzofuran (36724-16-0) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride In tetrahydrofuran at 25℃; for 0.5h; Schlenk technique; Inert atmosphere;	94%

2-(2-formyl-phenoxy)-hexanoic acid (138320-27-1) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
Stage #1: 2-(2-formyl-phenoxy)-hexanoic acid With triethylamine; p-toluenesulfonyl chloride In toluene at 70 - 80℃; for 2h; Stage #2: With sodium hydroxide In water; toluene at 70 - 75℃; for 2h;	90%
With sodium acetate; acetic anhydride at 90 - 100℃; Temperature; Reagent/catalyst; Large scale;	73.1%
With sodium acetate; acetic anhydride In acetic acid for 8h; Heating;	64%
With sodium acetate; acetic anhydride; acetic acid Heating;

1-hexynyl-2-(methoxymethoxy)benzene (125345-26-8) + 1,3-Dimethoxybenzene (151-10-0) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With gold(III) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 18h; Inert atmosphere;	87%

Hexane-1,2-diol (6920-22-5) + phenol (108-95-2) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With cyclopentene In toluene at 100℃; for 10h; Inert atmosphere; regioselective reaction;	85%

1-(2-bromophenyl)-hexan-2-one → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 105℃; for 22h;	82%

1-benzofurane (271-89-6) + 1-bromo-butane (109-65-9) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	82%
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	30%

2-iodophenyl acetate (32865-61-5) + hex-1-yne (693-02-7) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 70℃; for 20h;	81%

(2-Pentanoyloxy-benzyl)-triphenyl-phosphonium; bromide (70339-99-0) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With sodium tert-pentoxide In toluene Heating;	80%

2-(hex-1-yn-1-yl)phenol (125345-27-9) → 2-n-butylbenzo[b]furan (4265-27-4) + (E)-2-(1-(2-n-butyl-benzofuran-3-yl)hex-1-enyl)phenol (1244029-99-9) + (E)-2-(2-n-butyl-2-(2-n-butylbenzofuran-3-yl)vinyl)phenol (1244029-98-8)

Conditions	Yield
With [Rh(OH)(cod)]2; water; tris(2,6-dimethoxyphenyl)phosphine; lithium chloride In 1,4-dioxane at 90℃; for 24h;	A 7% B 12% C 80%

1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol (1248340-86-4) → 2-n-butylbenzo[b]furan (4265-27-4) + 3-butylbenzo[b]-furan (36724-27-3)

Conditions	Yield
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With n-butyllithium In tetrahydrofuran at 55℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h;	A 22% B 78%
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With n-butyllithium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h;	A 52% B 48%

methyl 2-bromohexanoate (5445-19-2) + salicylaldehyde (90-02-8) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85 - 90℃; for 8h; Reagent/catalyst; Solvent; Large scale;	77.7%
Stage #1: methyl 2-bromohexanoate; salicylaldehyde With Aliquat 336; caesium carbonate In ethyl acetate at 80℃; for 8h; Large scale; Stage #2: With sodium methylate In toluene for 5h; Reflux; Large scale;	38.6%

C12H14O2 → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With tert-butylisonitrile; palladium diacetate; caesium carbonate In acetonitrile at 20℃; for 15h;	76%

carbon dioxide (124-38-9) + 2-(hex-1-yn-1-yl)phenol (125345-27-9) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine; cobalt(II) bromide; zinc dibromide; 1,2-bis-(dicyclohexylphosphino)ethane In acetonitrile at 20℃; under 760.051 Torr; for 24h; Schlenk technique; Irradiation;	75%

2-(2-chloroacetyl)phenol (53074-73-0) + butyl magnesium bromide (693-04-9) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
Stage #1: 2-(2-chloroacetyl)phenol; butyl magnesium bromide In tetrahydrofuran; toluene at 20 - 55℃; for 1.5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; toluene	66%

methyl 2-(2-formylphenoxy)hexanoate (138320-26-0) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 5h; Reagent/catalyst; Solvent; Reflux;	65.1%
Multi-step reaction with 2 steps 1: K2CO3 / H2O; methanol / 2 h / Heating 2: Ac2O, AcONa, AcOH / Heating View Scheme
Multi-step reaction with 2 steps 1: 84 percent / aq. KOH / 2 h / Heating 2: 64 percent / Ac2O, AcONa / acetic acid / 8 h / Heating View Scheme

2-bromo-1-benzofuran (54008-77-4) + tri-n-butylbismuthine (3692-81-7) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere;	65%

1,2,3-trimethoxybenzene (621-23-8) + 1-hexynyl-2-(methoxymethoxy)benzene (125345-26-8) → 2-n-butylbenzo[b]furan (4265-27-4) + 3-(2,4,6-trimethoxybenzyl)-2-butylbenzofuran

Conditions	Yield
With gold(III) chloride; silver(I) triflimide In dichloromethane at 20℃; for 18h; Inert atmosphere;	A 11% B 64%

sodium phenoxide (139-02-6) + C20H18F6I2O6S2 → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
In methanol for 1h; Ambient temperature;	62%

sodium phenoxide (139-02-6) + 1-(1-hexynyliodonio)-4-phenyliodoniobenzene ditriflate → 2-n-butylbenzo[b]furan (4265-27-4) + (4-iodophenyl)(phenyl)iodonium trifluoromethanesulfonate (144930-55-2)

Conditions	Yield
In methanol at 0 - 20℃; for 12h; Cyclization;	A 62% B n/a

n-butyllithium (109-72-8, 29786-93-4) + 2-chlorobenzo[b]furan (63361-60-4) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In hexane at 40℃; for 24h; Inert atmosphere; Sealed tube;	59%

1,2,3-trimethoxybenzene (621-23-8) + 1-hexynyl-2-(methoxymethoxy)benzene (125345-26-8) → 2-n-butylbenzo[b]furan (4265-27-4) + 2-butyl-3-(methoxymethyl)benzofuran

Conditions	Yield
With platinum(II) chloride; cyclo-octa-1,5-diene In dichloromethane at 30℃; for 22h; Reagent/catalyst; Inert atmosphere;	A 11% B 58%

cyclohexenone (930-68-7) + 2-(hex-1-yn-1-yl)phenol (125345-27-9) → 3-(2-butylbenzofuran-3-yl)cyclohexanone + 2-n-butylbenzo[b]furan (4265-27-4) + (E)-2-(1-(2-n-butyl-benzofuran-3-yl)hex-1-enyl)phenol (1244029-99-9) + (E)-2-(2-n-butyl-2-(2-n-butylbenzofuran-3-yl)vinyl)phenol (1244029-98-8)

Conditions	Yield
With tol-BINAP; [Rh(OH)(cod)]2; water; lithium chloride In 1,4-dioxane at 90℃; for 6h;	A 9% B 14% C 2% D 47%

2-monochlorophenol (95-57-8) + hex-1-yne (693-02-7) → 2-n-butylbenzo[b]furan (4265-27-4) + phenol (108-95-2)

Conditions	Yield
In water; acetone; acetonitrile for 24h; Sonogashira reaction; Inert atmosphere; Photolysis;	A 42% B 16 %Chromat.
In water; acetone for 24h; Inert atmosphere; Photolysis;	A 30 %Chromat. B 45 %Chromat.

1,2,3-trimethoxybenzene (621-23-8) + 1-hexynyl-2-(methoxymethoxy)benzene (125345-26-8) → 2-n-butylbenzo[b]furan (4265-27-4) + 3-(2,4,6-trimethoxybenzyl)-2-butylbenzofuran + 2-butyl-3-(methoxymethyl)benzofuran

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; silver(I) triflimide In dichloromethane at 20℃; for 18h; Inert atmosphere;	A 37% B 27% C 18%

2-Iodophenol (533-58-4) + triethoxy(hex-1-yn-1-yl)silane (218793-76-1) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With cis-[((2,4,6-trimethylphenylamino)(morpholino)methylidene)]PdCl2(2,4,6-trimethylphenylisonitrile); mercury; sodium hydroxide In 1,4-dioxane; water at 80℃; for 4h; Reagent/catalyst; Hiyama Coupling;	24%

1-benzofurane (271-89-6) + 1-iodo-butane (542-69-8) → 2-n-butylbenzo[b]furan (4265-27-4)

Conditions	Yield
With n-butyllithium 1) Et2O, 0 deg C, 1 h; Yield given. Multistep reaction;

36%-hydrochloric acid + 2-n-butylbenzo[b]furan (4265-27-4) + 4-methoxy-benzoyl chloride (100-07-2) → 2-n-butyl 3-(4-methoxy benzoyl)-benzofuran (83790-87-8)

Conditions	Yield
With iron(III) chloride In water; toluene	100%
With iron(III) chloride In water; toluene

2-n-butylbenzo[b]furan (4265-27-4) → (R)-2-butyl-2,3-dihydrobenzofuran (1372790-92-5)

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (x)BF4*C27H27N2(1+); potassium tert-butylate; hydrogen In hexane; toluene at 25℃; under 7500.75 Torr; for 16h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction;	100%
With hydrogen; C39H36IrNOP(1+)*C32H12BF24(1-) In dichloromethane at 25℃; under 38002.6 Torr; for 24h; Autoclave; Glovebox; enantioselective reaction;	93%

2-n-butylbenzo[b]furan (4265-27-4) + 4-methoxy-benzoyl chloride (100-07-2) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -20 - -15℃; for 10h; Reflux;	92.8%
With aluminum (III) chloride In 1,2-dichloro-ethane at -10 - 60℃; for 7h; Temperature;	92%
With aluminum (III) chloride In 1,2-dichloro-ethane at -20 - -10℃; for 10h; Reflux; Large scale;	40.1%
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 2: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

2-n-butylbenzo[b]furan (4265-27-4) + 3,5-diiodo-4-(2-chloroethoxy)benzoyl chloride → 2-butyl-3-[3,5-diiodo-4-(2-chloroethoxy)benzoyl]benzofuran

Conditions	Yield
Stage #1: 3,5-diiodo-4-(2-chloroethoxy)benzoyl chloride With aluminum (III) chloride In dichloromethane at -5℃; for 1h; Stage #2: 2-n-butylbenzo[b]furan In dichloromethane at -5℃; for 13h;	85.4%

2-n-butylbenzo[b]furan (4265-27-4) + 4-methoxy-benzoyl chloride (100-07-2) → 2-n-butyl 3-(4-methoxy benzoyl)-benzofuran (83790-87-8)

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at -20 - -10℃; Solvent; Temperature; Reagent/catalyst; Large scale;	81.2%
With aluminum (III) chloride In dichloromethane at 20℃; for 24h; Inert atmosphere;	71%
Stage #1: 2-n-butylbenzo[b]furan With carbon disulfide for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 4-methoxy-benzoyl chloride With tin(IV) chloride at 0 - 20℃; for 75h;	64%
Stage #1: 4-methoxy-benzoyl chloride With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 1h; Stage #2: 2-n-butylbenzo[b]furan In dichloromethane at 5 - 25℃; for 2h;	10.6 g

2-n-butylbenzo[b]furan (4265-27-4) → 3-bromo-2-n-butylbenzo[b]furan (872400-06-1)

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 15h;	81%
With N-Bromosuccinimide In chloroform; acetonitrile at -8℃; for 1h;	80%
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 8h;	49%

2-n-butylbenzo[b]furan (4265-27-4) + C11H16O4 → 3-(2,4,6-trimethoxybenzyl)-2-butylbenzofuran

Conditions	Yield
With gold(III) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 18h; Inert atmosphere;	79%

phosgene (75-44-5) + 2-n-butylbenzo[b]furan (4265-27-4) + 1,1-dichloroethane (75-34-3) → 2-n-butyl 3-(4-methoxy benzoyl)-benzofuran (83790-87-8)

Conditions	Yield
With sodium hydrogencarbonate; aluminium chloride In water; methoxybenzene	78.7%

2-n-butylbenzo[b]furan (4265-27-4) + 4-bromo-benzaldehyde (1122-91-4) → 4-(2-butylbenzofuran-3-yl)benzaldehyde (1227008-77-6)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	78%

2-n-butylbenzo[b]furan (4265-27-4) → 2-butyl-2,3-dihydrobenzofuran (109209-69-0)

Conditions	Yield
With ruthenium; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; under 22502.3 Torr; for 48h; Autoclave; chemoselective reaction;	75%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); potassium tert-butylate; hydrogen; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In hexane at 60℃; under 48754.9 Torr; for 18h; Autoclave;
With hydrogen In neat (no solvent) at 80℃; under 7500.75 Torr; for 24h; Autoclave; chemoselective reaction;
With hydrogen In decalin at 180℃; under 37503.8 Torr; for 16h; Autoclave;

2-n-butylbenzo[b]furan (4265-27-4) + 1-Bromonaphthalene (90-11-9) → 2-butyl-3-(1-naphthyl)benzofuran (1227008-84-5)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	74%

Nitroethane (79-24-3) + 2-n-butylbenzo[b]furan (4265-27-4) → (E)-2-butyl-3-(2-nitrovinyl)benzofuran (1428338-31-1)

Conditions	Yield
With palladium(II) trifluoroacetate; silver(I) acetate In 1,2-dimethoxyethane; dimethyl sulfoxide at 100℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; regioselective reaction;	73%

2-n-butylbenzo[b]furan (4265-27-4) + 1-(3-Bromophenyl)ethanone (2142-63-4) → 1-[3-(2-butylbenzofuran-3-yl)phenyl]ethanone (1227008-83-4)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;	72%

Upstream product

• 32865-61-5 2-iodophenyl acetate 
• 693-02-7 hex-1-yne 
• 139-02-6 sodium phenoxide 
• 533-58-4 2-Iodophenol 
• 218793-76-1 triethoxy(hex-1-yn-1-yl)silane 
• 109-72-8 n-butyllithium 
• 63361-60-4 2-chlorobenzo[b]furan 
• 124-38-9 carbon dioxide 
• 125345-27-9 2-(hex-1-yn-1-yl)phenol 
• 90-02-8 salicylaldehyde 
• 125345-26-8 1-hexynyl-2-(methoxymethoxy)benzene 
• 151-10-0 1,3-Dimethoxybenzene 
• 621-23-8 1,2,3-trimethoxybenzene 
• 693-03-8 n-butyl magnesium bromide 

Downstream Products

• 796072-17-8 (4-bromo-phenyl)-(2-butyl-benzofuran-3-yl)-methanone 
• 83790-87-8 2-n-butyl 3-(4-methoxy benzoyl)-benzofuran 
• 52490-15-0 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran 
• 19774-82-4 amiodarone hydrochloride 
• 1951-26-4 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran 
• 85614-50-2 1-(benzofuran-2-yl)butan-1-one 
• 796072-22-5 4'-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-ylamine 
• 796072-21-4 2-butyl-3-[3'-nitro-4'-(3-phenyl-propoxy)-biphenyl-4-ylmethyl]-benzofuran 
• 796072-20-3 2-butyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-benzofuran 
• 796071-95-9 N-[4'-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid 
• 39478-05-2 2-butyl-3-phenylbenzofuran 
• 1227008-83-4 1-[3-(2-butylbenzofuran-3-yl)phenyl]ethanone 
• 1227008-77-6 4-(2-butylbenzofuran-3-yl)benzaldehyde 
• 63420-09-7 2-n-butyl-3-[N-(4-methyl-benzenesulfonyl)-4-aminobenzoyl]-benzofuran 

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