4-CHLOROFURO[3,2-C]PYRIDINE Chemical Properties

Melting point:

41 °C

Boiling point:

243℃

Density 

1.377

Flash point:

101℃

storage temp. 

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

form 

solid

pka

-0.69±0.30(Predicted)

color 

Orange

InChI

InChI=1S/C7H4ClNO/c8-7-5-2-4-10-6(5)1-3-9-7/h1-4H

InChIKey

OPFFYLJLHPZSEO-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC2OC=CC1=2

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2932190090

4-CHLOROFURO[3,2-C]PYRIDINE Usage And Synthesis

Definition

ChEBI: 4-Chlorofuro[3,2-c]pyridine is a furopyridine.

Synthesis

General procedure for the synthesis of 4-chlorofuranylpyridine from 4,5-dihydro-4-oxofuro[3,2]pyridine: cf. Example 4 Synthesis of 4-chlorofuro[3,2-c]pyridine. 4,5-Dihydro-4-oxofuro[3,2]pyridine (72.2 g, 534 mmol) was added to phosphorochloridic acid (100 mL) preheated to 120 °C with continuous stirring for 30 min. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Ice-cooled water was added to the residue and the pH was adjusted to basic with 8 M aqueous sodium hydroxide, followed by extraction with ethyl acetate. The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was again removed by distillation under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=30/70) to afford the target product 4-chlorofuranylpyridine (66.1 g, 81% yield). The product was characterized by 1H-NMR (CDCl3): δ 7.13 (1H, dd, J = 2.2, 1.0 Hz), 7.79 (1H, dd, J = 5.8, 1.0 Hz), 8.27 (1H, d, J = 2.2 Hz), 8.32 (1H, d, J = 5.8 Hz).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 6, p. 1147 - 1156
[3] Patent: EP2100895, 2009, A1. Location in patent: Page/Page column 44-45
[4] Bulletin de la Societe Chimique de France, 1971, p. 1727 - 1730
[5] Archiv der Pharmazie, 1981, vol. 314, # 2, p. 156 - 162

4-CHLOROFURO[3,2-C]PYRIDINE(31270-80-1)Related Product Information

• OTAVA-BB 1199329
• 5-Bromofuro[2,3-b]pyridine
• Furo[2,3-b]pyridine
• Furo[3,2-b]pyridine,4-oxide(9CI)
• furo[3,2-b]pyridine
• Furo[3,2-b]pyridine-2-carboxaldehyde (9CI)
• 2-b]pyridine
• Furo[3,2-c]pyridine
• 4-chlorofuro[3,2-c]pyridine-7-carboxylicacid
• Furo[3,2-c]pyridine-2-carboxaldehyde (9CI)
• Ethanone, 1-furo[2,3-b]pyridin-5-yl- (9CI)
• 4-CHLOROFURO[3,2-C]PYRIDINE
• 7-CHLOROFURO[2,3-C]PYRIDINE
• 3-(Carboxymethyl)-6-chlorofuro[3,2-b]pyridine-2-carboxylic acid
• 2-(Carboxymethyl)-6-chlorofuro[3,2-b]pyridine-3-carboxylic acid
• AKOS 92637
• SALOR-INT L299553-1EA