| Identification | More | [Name]
1-Benzofuran-5-carbaldehyde | [CAS]
10035-16-2 | [Synonyms]
1-BENZOFURAN-5-CARBALDEHYDE
5-FORMYLBENZO[BETA]FURAN
5-FORMYLBENZO(B)FURAN
5-Formylbenzofuran
Benzofuran-5-carboxaldehyde
Benzofurancarbaldehyde
Benzo[b]furan-5-carboxaldehyde 96%
5-Formylbenzo[beta]furan, min. 96 %
Benzo[b]furan-5-carboxaldehyde
5-Benzofurancarbaldehyde
Benzofuran-5-carbaldehyde | [EINECS(EC#)]
685-962-1 | [Molecular Formula]
C9H6O2 | [MDL Number]
MFCD03411182 | [Molecular Weight]
146.14 | [MOL File]
10035-16-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [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) | [Storage Precautions]
Store under inert gas;Air sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2932990090 |
| Hazard Information | Back Directory | [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 |
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
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https://www.jkchemical.com |
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