1-Benzofuran-5-carbaldehyde Chemical Properties

Melting point:

50.5

Boiling point:

70-74°C 0,15mm

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

low melting solid

color 

Light yellow crystalline

InChI

InChI=1S/C9H6O2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-6H

InChIKey

LLLBDLDNTMMZHL-UHFFFAOYSA-N

SMILES

O1C2=CC=C(C=O)C=C2C=C1

CAS DataBase Reference

10035-16-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

HazardClass 

IRRITANT

HS Code 

2932990090

1-Benzofuran-5-carbaldehyde Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

1-Benzofuran-5-carbaldehyde is a building block used as a reactant in the synthetic preparation of benzofuranyl oxadiazoles as inhibitors of glycogen synthase kinase-3β with good brain permeability. It is also used in the synthesis of pyrroloquinolone PDE5 inhibitors used for clinical studies on erectile dysfunction.

Synthesis

General procedure for the synthesis of benzofuran-5-carbaldehyde from 2,3-dihydrobenzofuran-5-carbaldehyde: N-bromosuccinimide (NBS, 0.656 g, 3.69 mmol) and azobisisobutyronitrile (AIBN, 8.10 mg, 49.2 μmol) were added to a solution of chlorobenzene (7.3 mL) at room temperature and under argon protection to 2,3-dihydrobenzofuran-5-carbaldehyde (0.364 g, 2.46 mmol) in a solution of chlorobenzene (7.3 mL). The reaction mixture was stirred at 80 °C for 1 h before being cooled to room temperature and diluted with ethyl acetate (EtOAc). The organic layer was washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and brine, dried over anhydrous sodium sulfate (Na2SO4) and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 3:97) to afford benzofuran-5-carbaldehyde (0.268 g, 1.84 mmol, 75% yield) as a colorless oil. Its 1H-NMR (CDCl3, 400 MHz) data were as follows: δ 6.82 (d, J = 2.0 Hz, 1H, furan-H), 7.54 (d, J = 8.8 Hz, 1H, Ar-H), 7.65 (d, J = 2.0 Hz, 1H, furan-H), 7.79 (d, J = 8.8 Hz, 1H, Ar-H), 8.07 (s 1H, Ar-H), 9.99 (s, 1H, -CHO). The spectral data of the obtained compounds are in agreement with literature reports (van Otterlo et al., 2005).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6270 - 6286
[2] Phytochemistry, 2013, vol. 96, p. 132 - 147
[3] Patent: US2014/309427, 2014, A1. Location in patent: Paragraph 0074; 0075; 0076; 0077
[4] Patent: WO2018/64135, 2018, A1. Location in patent: Paragraph 0174-0177

1-Benzofuran-5-carbaldehyde(10035-16-2)Related Product Information

• 4-Dimethylaminobenzaldehyde
• Benzaldehyde
• 4-Nitrobenzaldehyde
• Benzofuran
• 4-Hydroxybenzaldehyde
• o-Phthalaldehyde
• Furfural
• p-Anisaldehyde
• PONGAMOL
• VISNAGIN
• Iprocrolol
• KARANJIN
• sodium benzaldehyde-o-sulfonate
• KHELLIN
• Furobufen
• KHELLINONE
• 2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE
• 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE