3-Bromopyridine-4-methanol Chemical Properties

Boiling point:

287.1±25.0 °C(Predicted)

Density 

1.668±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

12.72±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C6H6BrNO/c7-6-3-8-2-1-5(6)4-9/h1-3,9H,4H2

InChIKey

LQBUZBOVEZBDEB-UHFFFAOYSA-N

SMILES

C1=NC=CC(CO)=C1Br

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

Storage Class

11 - Combustible Solids

3-Bromopyridine-4-methanol Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-bromopyridine-4-methanol from 3-bromopyridine-4-aldehyde: To a solution of 3-bromo-4-pyridinecarboxaldehyde (3.0 g, 16.2 mmol) in anhydrous methanol (40 mL) was slowly added NaBH4 (0.736 g, 19.5 mmol) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 2 h under nitrogen protection. After completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, water and ethyl acetate were added for extraction, and the organic layer was separated and washed with distilled water, dried over anhydrous Na2SO4, and finally concentrated under reduced pressure to obtain the target product 3-bromopyridine-4-methanol (3.021 g, 100% yield) as a white powder. The structure of the product was determined by 1H NMR (CDCl3, 300 MHz, 298K, δ ppm): 8.61 (s, 1H), 8.51 (d, 1H, J = 4.8 Hz), 7.55 (d, 1H, J = 4.8 Hz), 4.76 (s, 2H), 2.89 (s, 1H); 13C NMR (CDCl3, 75.5MHz, 298K, δ ppm) 298K, δ ppm): 151.14, 149.45, 148.54, 122.47, 119.90, 63.47; GC/MS (m/z): 188; IR (KBr, v, cm-1): 3152, 2894, 2829, 1593, 1447, 1401, 1333, 1223, 1170. 1070, 1024, 834, 705, 599 Confirmed.

References

[1] Patent: EP2759536, 2014, A1. Location in patent: Paragraph 0067; 0068
[2] Patent: WO2014/114742, 2014, A1. Location in patent: Page/Page column 25
[3] Patent: WO2015/25172, 2015, A1. Location in patent: Page/Page column 90
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 20, p. 8309 - 8313
[5] Organic Letters, 2008, vol. 10, # 13, p. 2701 - 2704