Product Name

  • Name

    1-BENZOFURAN-6-CARBALDEHYDE

  • EINECS
  • CAS No. 123297-88-1
  • Article Data9
  • CAS DataBase
  • Density 1.238 g/cm3
  • Solubility
  • Melting Point
  • Formula C9H6O2
  • Boiling Point 251.549 °C at 760 mmHg
  • Molecular Weight 146.145
  • Flash Point 110.192 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 123297-88-1 (1-BENZOFURAN-6-CARBALDEHYDE)
  • Hazard Symbols
  • Synonyms 6-Formyl-2H-1-benzo[b]furan;
  • PSA 30.21000
  • LogP 2.24530

Synthetic route

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

6-bromo-benzofuran
128851-73-0

6-bromo-benzofuran

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

N,N-dimethyl-formamide

2-(3-bromophenoxy)acetaldehyde diethyl acetal
204452-94-8

2-(3-bromophenoxy)acetaldehyde diethyl acetal

A

benzofuran-7-carboxaldehyde
95333-14-5

benzofuran-7-carboxaldehyde

B

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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%
...Expand
carbon monoxide
201230-82-2

carbon monoxide

trifluoromethanesulfonic acid benzofuran-6-yl ester
227752-25-2

trifluoromethanesulfonic acid benzofuran-6-yl ester

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

N,N-dimethyl-formamide

2-(3-bromophenoxy)acetaldehyde diethyl acetal
204452-94-8

2-(3-bromophenoxy)acetaldehyde diethyl acetal

A

benzofuran-4-carboxaldehyde
95333-13-4

benzofuran-4-carboxaldehyde

B

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
With PPA; tert.-butyl lithium 1.) benzene, reflux, 2.) Et2O, -78 deg C, 3.) Et2O; Multistep reaction;
...Expand
6-hydroxybenzofuran
13196-11-7

6-hydroxybenzofuran

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

6-hydroxybenzofuran-3-one

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

6-(tert-butyl-dimethylsilanyloxy)-[2H]-benzofuran-3-one

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

3-hydroxy-6-silyloxy-[2,3]dihydrobenzofuran

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

3-Bromophenol

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

2-(3-bromophenoxy)acetaldehyde diethyl acetal

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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

3-Bromophenol

A

benzofuran-7-carboxaldehyde
95333-14-5

benzofuran-7-carboxaldehyde

B

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

Conditions
ConditionsYield
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-carboxaldehyde

benzofuran-6-carboxylic acid
77095-51-3

benzofuran-6-carboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In water at 75 - 90℃;70%
1-bromo-2-(triisopropylsilyl)acetylene
111409-79-1

1-bromo-2-(triisopropylsilyl)acetylene

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

5-((triisopropylsilyl)ethynyl)benzofuran-6-carbaldehyde

5-((triisopropylsilyl)ethynyl)benzofuran-6-carbaldehyde

Conditions
ConditionsYield
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-carboxaldehyde

benzofuran-6-carbaldehyde oxime

benzofuran-6-carbaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; potassium carbonate In ethanol; water at 20℃;41%
Methyl azidoacetate
1816-92-8

Methyl azidoacetate

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

(Z)-methyl 2-azido-3-(benzofuran-6-yl)acrylate
1279721-92-4

(Z)-methyl 2-azido-3-(benzofuran-6-yl)acrylate

Conditions
ConditionsYield
With sodium methylate In methanol at -20 - -10℃; Inert atmosphere;38%
nitromethane
75-52-5

nitromethane

benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

6-((E)-2-Nitro-vinyl)-benzofuran

6-((E)-2-Nitro-vinyl)-benzofuran

Conditions
ConditionsYield
With sodium hydroxide at 15℃;
benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

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

4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

3-Benzofuran-6-yl-2-(4-methoxy-benzoyl)-4-nitro-butyric acid ethyl ester
1025833-28-6

3-Benzofuran-6-yl-2-(4-methoxy-benzoyl)-4-nitro-butyric acid ethyl ester

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

(2S,3S,4S)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

(2S,3S,4S)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

(2R,3S,4S)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

(2R,3S,4S)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

(2S,3S,4R)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

(2S,3S,4R)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

(2R,3S,4R)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

(2R,3S,4R)-4-Benzofuran-6-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

methyl 5H-furo[2,3-f]indole-6-carboxylate
1279721-95-7

methyl 5H-furo[2,3-f]indole-6-carboxylate

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

ethyl 2-(bis(2-isopropylphenoxy)phosphoryl)acetate
188945-44-0

ethyl 2-(bis(2-isopropylphenoxy)phosphoryl)acetate

A

(Z)-ethyl 3-(benzofuran-6-yl)acrylate
1499179-58-6

(Z)-ethyl 3-(benzofuran-6-yl)acrylate

B

3-(6-[2,3]dihydrobenzofuran)-2-propenoic acid
227751-62-4

3-(6-[2,3]dihydrobenzofuran)-2-propenoic acid

Conditions
ConditionsYield
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
...Expand
benzofuran-6-carboxaldehyde
123297-88-1

benzofuran-6-carboxaldehyde

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

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

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

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

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

Conditions
ConditionsYield
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

benzofuran-6-carboxaldehyde

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

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

Conditions
ConditionsYield
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

6-Benzofurancarboxaldehyde Specification

This chemical is called 6-Benzofurancarboxaldehyde, and its systematic name is 1-benzofuran-6-carbaldehyde. With the molecular formula of C9H6O2, its molecular weight is 146.14. The CAS registry number of this chemical is 123297-88-1. Additionally, its product category is Aldehyde.

Other characteristics of the 6-Benzofurancarboxaldehyde can be summarised as followings: (1)ACD/LogP: 1.96; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 23; (6)ACD/BCF (pH 7.4): 23; (7)ACD/KOC (pH 5.5): 327; (8)ACD/KOC (pH 7.4): 327; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 30.21 Å2; (13)Index of Refraction: 1.652; (14)Molar Refractivity: 43.148 cm3; (15)Molar Volume: 118.01 cm3; (16)Polarizability: 17.105×10-24cm3; (17)Surface Tension: 47.707 dyne/cm; (18)Density: 1.238 g/cm3; (19)Flash Point: 110.192 °C; (20)Enthalpy of Vaporization: 48.886 kJ/mol; (21)Boiling Point: 251.549 °C at 760 mmHg; (22)Vapour Pressure: 0.02 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
1.SMILES: O=Cc1ccc2ccoc2c1
2.InChI: InChI=1/C9H6O2/c10-6-7-1-2-8-3-4-11-9(8)5-7/h1-6H
3.InChIKey: HLSNQZQSNWFXET-UHFFFAOYAJ

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