4-(3-Pyridyl)-1-butanol

4-(3-Pyridyl)-1-butanol Property

Boiling point:

115-125 °C(Press: 0.5 Torr)

Density 

1.035±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

15.10±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

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.

4-(3-Pyridyl)-1-butanol Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-(3-pyridinyl)-1-butyn-1-ol from 4-(3-pyridinyl)-3-butyn-1-ol: 4-(3-pyridinyl)-3-butyn-1-ol (0.32 g, 2.2 mmol) was dissolved in EtOH (44 mL) and passed through a H-Cube?flow hydrogenation reactor fitted with 10% Pd/C catalyst to carry out the hydrogenation reaction (flow rate : 1.0 mL/min; pressure: 1.0 bar; temperature: 3.5°C). After completion of the reaction, the output solution was concentrated to dryness to give an oily residue (0.31 g). Purification by conventional silica gel fast chromatography (eluent: CH2Cl2/MeOH, 95:5) afforded pure 4-(3-pyridyl)-1-butanol (0.294 g, 89% yield) as a colorless liquid. rf = 1.16 mm. m/z MS (ESI) m/z: 152 [M-H]-. 1H NMR (DMSO-d6) δ: 8.43 (m. 1H), 8.38 (dd, 1H, J = 4.8, 1.5 Hz), 7.61 (dt, 1H, J = 7.8, 2.1 Hz), 7.30 (dd, 1H, J = 7.8, 4.8 Hz), 4.37 (t, 1H, J = 5.2 Hz), 3.41 (q, 2H, J = 5.2 Hz), 2.59 (t, 2H, J = 7.7 Hz), 1.64-1.55 (m, 2H), 1.47-1.38 (m, 2H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2573 - 2590
[2] Patent: WO2014/144836, 2014, A2. Location in patent: Paragraph 0614; 0615
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080