4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE Chemical Properties

Melting point:

166-167℃

Boiling point:

392.9±37.0 °C(Predicted)

Density 

1.81

storage temp. 

2-8°C(protect from light)

pka

8.03±0.31(Predicted)

InChI

InChI=1S/C13H8INO/c14-12-7-11(5-6-13(12)16)10-3-1-9(8-15)2-4-10/h1-7,16H

InChIKey

GGJLASJZXUIMAG-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(O)C(I)=C2)=CC=C(C#N)C=C1

Safety Information

HS Code 

2926907090

4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE Usage And Synthesis

Uses

4''-Hydroxy-3''-iodobiphenyl-4-carbonitrile is the major component of the byproduct in the synthesis of 4''-Hydroxy-3'',5''-diiodo-[1,1''-biphenyl]-4-carbonitrile (H005080), which is a useful building block compound, and has been used in the preparation of plasminogen activator inhibitor antagonists.

Synthesis

4'-Hydroxy-4'-cyanobiphenyl (6.00 g, 30.8 mmol) was used as a raw material, which was dissolved in methanol (90 mL) at 0 °C, and sodium iodide (4.61 g, 30.8 mmol) and sodium hydroxide (1.23 g, 30.8 mmol) were added sequentially. Subsequently, aqueous sodium hypochlorite (47 mL, 5.25% Clorox, 2.29 g, 30.8 mmol) was slowly added at 45 °C. The reaction mixture was stirred at 0 °C for 1 h and then gradually warmed up to room temperature. The reaction mixture was diluted with sodium thiosulfate solution (10 mL) and water (80 mL) and the pH was adjusted to 7 by addition of sodium dihydrogen phosphate. the mixture was extracted with dichloromethane (2 x 90 mL), the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a white powder. The crude product was crystallized by dichloroethane/hexane and purified by chromatography on a silica gel column with dichloromethane to give 4'-hydroxy-3'-iodobiphenyl-4-carbonitrile (5.19 g, 53% yield). Mass spectrum (DCI) m/z 339 [M + NH4]+.

References

[1] Organic Process Research and Development, 2005, vol. 9, # 1, p. 45 - 50
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 3, p. 689 - 693
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 38 - 55
[4] Patent: US2003/153548, 2003, A1
[5] Patent: US2003/134835, 2003, A1

4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE(460746-47-8)Related Product Information

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