2-BROMO-6-IODO-3-METHOXYPYRIDINE Chemical Properties

Boiling point:

315.7±42.0 °C(Predicted)

Density 

2.166±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-6.51±0.10(Predicted)

form 

solid

Appearance

White to yellow Solid

InChI

InChI=1S/C6H5BrINO/c1-10-4-2-3-5(8)9-6(4)7/h2-3H,1H3

InChIKey

LHDNVVCKJSWJKM-UHFFFAOYSA-N

SMILES

C1(Br)=NC(I)=CC=C1OC

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933399990

2-BROMO-6-IODO-3-METHOXYPYRIDINE Usage And Synthesis

Synthesis

Stage 1(b): synthesis of 2-bromo-6-iodo-3-methoxypyridine (3). Potassium carbonate (K2CO3, 6.22 g, 45.1 mmol) and iodomethane (CH3I, 24.6 g, 10.77 mL, 173.3 mmol) were sequentially added to a solution of N,N-dimethylformamide (DMF, 30 mL) in which 2-bromo-6-iodo-pyridin-3-ol (2, 14.9 g, 49.5 mmol) was dissolved. The reaction mixture was heated and stirred at 100 °C for 2 h and subsequently cooled to room temperature. Reaction termination was achieved by addition of water (H2O) and stirring was continued for 30 min. The precipitate formed was collected by filtration, washed with water and dried in air to give light brown solid product 3 (15.7 g, 100% yield). The product was characterized by the following data: 1H NMR (CDCl3) δ 7.61 (d, 1H, J = 8.4 Hz), 6.86 (d, 1H, J = 8.4 Hz), 3.93 (s, 3H); mass spectral observation m/z = 314 (M + 1), 315.

References

[1] Patent: US2008/45561, 2008, A1. Location in patent: Page/Page column 25; 22
[2] Organic Letters, 2000, vol. 2, # 26, p. 4201 - 4204
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6435 - 6446
[4] Patent: WO2014/43252, 2014, A2. Location in patent: Page/Page column 45-46
[5] Patent: WO2007/88999, 2007, A1. Location in patent: Page/Page column 166

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