3-Phenylpyridine-5-carboxaldehyde

3-Phenylpyridine-5-carboxaldehyde Property

Boiling point:

355.8±30.0 °C(Predicted)

Density 

1.147±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.05±0.20(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Phenylpyridine-5-carboxaldehyde Chemical Properties,Usage,Production

Synthesis

General steps for the synthesis of 5-phenylpyridine-3-carbaldehyde: 1. reaction mixture preparation: 5-bromopyridine-3-carboxaldehyde (0.500 g, 2.69 mmol), tetrakis(triphenylphosphine)palladium (0.155 g, 0.134 mmol), and phenylboronic acid (0.492 g, 4.03 mmol) were dissolved in a biphasic mixture of degassed 2.0 M aqueous Na2CO3 solution (6.0 mL) and toluene (6.7 mL). 2. Reaction conditions: the mixture was heated to reflux for 2.5 hours. 3. Post-treatment: After completion of the reaction, the mixture was cooled to room temperature and diluted with water and ethyl acetate (EtOAc). The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate (1x). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give an orange-brown oil (0.848 g). 4. Purification: 5-phenylpyridine-3-carbaldehyde (0.447 g, 91% yield) was purified by silica gel column chromatography as a light yellow solid. 5. Characterization: 1H NMR (500MHz, CDCl3) δ: 10.19 (s, 1H), 9.07 (s, 1H), 9.04 (s, 1H), 8.34 (s, 1H), 7.62 (d, J = 7.7Hz, 2H), 7.52 (t, J = 7.7Hz, 2H), 7.47-7.44 (m, 1H). Mass spectrum (MS): 184.2 (M + H)+; 216.2 (M + CH3OH + H)+.

References

[1] Patent: WO2007/70818, 2007, A1. Location in patent: Page/Page column 95
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2012, vol. 67, # 1, p. 75 - 84
[3] Patent: US2014/296528, 2014, A1. Location in patent: Sheet 4