123297-88-1

Basic information

• Product Name: 1-BENZOFURAN-6-CARBALDEHYDE
• Synonyms: 1-BENZOFURAN-6-CARBALDEHYDE;6-Benzofurancarboxaldehyde (9CI);6-Benzofurancarboxaldehyde;6-Formyl-2H-1-benzo[b]furan;benzofuran-6-carbaldehyde
• CAS NO: 123297-88-1
• Molecular Formula: C₉H₆O₂
• Molecular Weight: 146.14274
• Product Categories: ALDEHYDE
• Mol File: 123297-88-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 252℃
• Flash Point: 110℃
• Appearance: /
• Density: 1.238
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1-BENZOFURAN-6-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZOFURAN-6-CARBALDEHYDE(123297-88-1)
• EPA Substance Registry System: 1-BENZOFURAN-6-CARBALDEHYDE(123297-88-1)

Safety Data

• Hazardous Substances Data: 123297-88-1(Hazardous Substances Data)

Usage

General Description

1-Benzofuran-6-carbaldehyde is a chemical compound that belongs to the benzofuran family. It is a pale yellow liquid with a floral, woody odor, and is commonly used in the fragrance and flavor industry. This chemical is also used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals.

Synthetic route

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 6-bromo-benzofuran (128851-73-0) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Stage #1: 6-bromo-benzofuran With isopropylmagnesium bromide In tetrahydrofuran at -25℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -25℃;	80%
Stage #1: 6-bromo-benzofuran With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether; pentane at -78 - 0℃; for 0.5h; Inert atmosphere;	54%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 2-(3-bromophenoxy)acetaldehyde diethyl acetal (204452-94-8) → benzofuran-7-carboxaldehyde (95333-14-5) + benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Stage #1: 2-(3-bromophenoxy)acetaldehyde diethyl acetal In toluene for 3h; Reflux; Stage #2: N,N-dimethyl-formamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;	A n/a B 34%

carbon monoxide (201230-82-2) + trifluoromethanesulfonic acid benzofuran-6-yl ester (227752-25-2) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
With palladium diacetate; triethylamine; diphenylphosphinopropane; tri-n-octylsilane In N,N-dimethyl-formamide at 70℃; for 2h;	29%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 2-(3-bromophenoxy)acetaldehyde diethyl acetal (204452-94-8) → benzofuran-4-carboxaldehyde (95333-13-4) + benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
With PPA; tert.-butyl lithium 1.) benzene, reflux, 2.) Et2O, -78 deg C, 3.) Et2O; Multistep reaction;

6-hydroxybenzofuran (13196-11-7) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / triethylamine / CH2Cl2 / 1.5 h / 0 - 20 °C 2: 29 percent / Pd(OAc)2; diphenylphosphinopropane; triethylamine / trioctylsilane / dimethylformamide / 2 h / 70 °C View Scheme

6-hydroxybenzofuran-3-one (6272-26-0) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: triethylamine / dimethylformamide / 2 h / 20 °C 2: NaBH4 / methanol / 1 h / 20 °C 3: 6.93 g / aq. HCl / dioxane / 24 h / 20 °C 4: 96 percent / triethylamine / CH2Cl2 / 1.5 h / 0 - 20 °C 5: 29 percent / Pd(OAc)2; diphenylphosphinopropane; triethylamine / trioctylsilane / dimethylformamide / 2 h / 70 °C View Scheme

6-(tert-butyl-dimethylsilanyloxy)-[2H]-benzofuran-3-one (299912-77-9) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4 / methanol / 1 h / 20 °C 2: 6.93 g / aq. HCl / dioxane / 24 h / 20 °C 3: 96 percent / triethylamine / CH2Cl2 / 1.5 h / 0 - 20 °C 4: 29 percent / Pd(OAc)2; diphenylphosphinopropane; triethylamine / trioctylsilane / dimethylformamide / 2 h / 70 °C View Scheme

3-hydroxy-6-silyloxy-[2,3]dihydrobenzofuran (1056942-29-0) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 6.93 g / aq. HCl / dioxane / 24 h / 20 °C 2: 96 percent / triethylamine / CH2Cl2 / 1.5 h / 0 - 20 °C 3: 29 percent / Pd(OAc)2; diphenylphosphinopropane; triethylamine / trioctylsilane / dimethylformamide / 2 h / 70 °C View Scheme

3-Bromophenol (591-20-8) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF 2: 1.) polyphosphoric acid, 2.) t-BuLi / 1.) benzene, reflux, 2.) Et2O, -78 deg C, 3.) Et2O View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / dimethyl sulfoxide / 12 h / 20 - 160 °C / Inert atmosphere 2.1: polyphosphoric acid (PPA) / toluene / 4 h / 20 °C / Inert atmosphere; Reflux 3.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 0 °C / Inert atmosphere View Scheme

2-(3-bromophenoxy)acetaldehyde diethyl acetal (204452-94-8) → benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: polyphosphoric acid (PPA) / toluene / 4 h / 20 °C / Inert atmosphere; Reflux 2.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 0 °C / Inert atmosphere View Scheme

3-Bromophenol (591-20-8) → benzofuran-7-carboxaldehyde (95333-14-5) + benzofuran-6-carboxaldehyde (123297-88-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 100 °C 2.1: polyphosphoric acid / toluene / 3 h / Reflux 2.2: 2 h / -78 °C View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → benzofuran-6-carboxylic acid (77095-51-3)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In water at 75 - 90℃;	70%

1-bromo-2-(triisopropylsilyl)acetylene (111409-79-1) + benzofuran-6-carboxaldehyde (123297-88-1) → 5-((triisopropylsilyl)ethynyl)benzofuran-6-carbaldehyde

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; lithium acetate; 3,5-Bis-(trifluoromethyl)aniline; silver carbonate; trifluoroacetic acid In 1,2-dichloro-ethane at 70℃; Inert atmosphere; Sealed tube;	53%

benzofuran-6-carboxaldehyde (123297-88-1) → benzofuran-6-carbaldehyde oxime

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In ethanol; water at 20℃;	41%

Methyl azidoacetate (1816-92-8) + benzofuran-6-carboxaldehyde (123297-88-1) → (Z)-methyl 2-azido-3-(benzofuran-6-yl)acrylate (1279721-92-4)

Conditions	Yield
With sodium methylate In methanol at -20 - -10℃; Inert atmosphere;	38%

nitromethane (75-52-5) + benzofuran-6-carboxaldehyde (123297-88-1) → 6-((E)-2-Nitro-vinyl)-benzofuran

Conditions	Yield
With sodium hydroxide at 15℃;

benzofuran-6-carboxaldehyde (123297-88-1) → 4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester (1026183-98-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 50percent aq. NaOH / 15 °C 2: DBU / propan-2-ol; tetrahydrofuran 3: H2 / W-2 Raney Ni / ethyl acetate / 3040 Torr View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → 3-Benzofuran-6-yl-2-(4-methoxy-benzoyl)-4-nitro-butyric acid ethyl ester (1025833-28-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50percent aq. NaOH / 15 °C 2: DBU / propan-2-ol; tetrahydrofuran View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → (2S,3S,4S)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 50percent aq. NaOH / 15 °C 2: DBU / propan-2-ol; tetrahydrofuran 3: H2 / W-2 Raney Ni / ethyl acetate / 3040 Torr 4: NaBH3CN, HCl / ethanol; tetrahydrofuran View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → (2R,3S,4S)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 50percent aq. NaOH / 15 °C 2: DBU / propan-2-ol; tetrahydrofuran 3: H2 / W-2 Raney Ni / ethyl acetate / 3040 Torr 4: NaBH3CN, HCl / ethanol; tetrahydrofuran View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → (2S,3S,4R)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 50percent aq. NaOH / 15 °C 2: DBU / propan-2-ol; tetrahydrofuran 3: H2 / W-2 Raney Ni / ethyl acetate / 3040 Torr 4: NaBH3CN, HCl / ethanol; tetrahydrofuran View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → (2R,3S,4R)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 50percent aq. NaOH / 15 °C 2: DBU / propan-2-ol; tetrahydrofuran 3: H2 / W-2 Raney Ni / ethyl acetate / 3040 Torr 4: NaBH3CN, HCl / ethanol; tetrahydrofuran View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → methyl 5H-furo[2,3-f]indole-6-carboxylate (1279721-95-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate / methanol / -20 - -10 °C / Inert atmosphere 2: iron(II) triflate / tetrahydrofuran / 24 h / 80 °C / Sealed tube; Inert atmosphere View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) + ethyl 2-(bis(2-isopropylphenoxy)phosphoryl)acetate (188945-44-0) → (Z)-ethyl 3-(benzofuran-6-yl)acrylate (1499179-58-6) + 3-(6-[2,3]dihydrobenzofuran)-2-propenoic acid (227751-62-4)

Conditions	Yield
Stage #1: ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at -78℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: benzofuran-6-carboxaldehyde In tetrahydrofuran; methanol at -78℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Overall yield = 82 %; diastereoselective reaction;	A n/a B n/a

benzofuran-6-carboxaldehyde (123297-88-1) → (+/-)-3-(benzofuran-6-yl)-4-(2,4-dimethoxybenzyl)-4H-1'-azaspiro[[1,2,4]oxadiazole-5,3'-bicyclo[2.2.2]octane]

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; potassium carbonate / ethanol; water / 20 °C 2: sodium hypochlorite / water; dichloromethane / 2 h / 0 - 20 °C View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → (R)-3-(benzofuran-6-yl)-4-(2,4-dimethoxybenzyl)-4H-1'-azaspiro[[1,2,4]oxadiazole-5,3'-bicyclo[2.2.2]octane]

Conditions	Yield
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; potassium carbonate / ethanol; water / 20 °C 2: sodium hypochlorite / water; dichloromethane / 2 h / 0 - 20 °C 3: ammonium hydroxide / ethanol / Resolution of racemate View Scheme

benzofuran-6-carboxaldehyde (123297-88-1) → (S)-3-(benzofuran-6-yl)-4-(2,4-dimethoxybenzyl)-4H-1'-azaspiro[[1,2,4]oxadiazole-5,3'-bicyclo[2.2.2]octane]

Conditions	Yield
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; potassium carbonate / ethanol; water / 20 °C 2: sodium hypochlorite / water; dichloromethane / 2 h / 0 - 20 °C 3: ammonium hydroxide / ethanol / Resolution of racemate View Scheme

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 204452-94-8 2-(3-bromophenoxy)acetaldehyde diethyl acetal 
• 201230-82-2 carbon monoxide 
• 227752-25-2 trifluoromethanesulfonic acid benzofuran-6-yl ester 
• 13196-11-7 6-hydroxybenzofuran 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 299912-77-9 6-(tert-butyl-dimethylsilanyloxy)-[2H]-benzofuran-3-one 
• 1056942-29-0 3-hydroxy-6-silyloxy-[2,3]dihydrobenzofuran 
• 591-20-8 3-Bromophenol 
• 128851-73-0 6-bromo-benzofuran 

Downstream Products

• 1026183-98-1 4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester 
• 1025833-28-6 3-Benzofuran-6-yl-2-(4-methoxy-benzoyl)-4-nitro-butyric acid ethyl ester 
• 77095-51-3 benzofuran-6-carboxylic acid 
• 1025967-78-5 (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid 

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