2-Bromo-3-hydroxy-6-methylpyridine Chemical Properties

Melting point:

186-187 °C

Boiling point:

311.8±37.0 °C(Predicted)

Density 

1.655±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

4.66±0.10(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C6H6BrNO/c1-4-2-3-5(9)6(7)8-4/h2-3,9H,1H3

InChIKey

UHMANLXCLQNQJD-UHFFFAOYSA-N

SMILES

C1(Br)=NC(C)=CC=C1O

Safety Information

Risk Statements 

36/37/38

Safety Statements 

24/25

HS Code 

29333990

2-Bromo-3-hydroxy-6-methylpyridine Usage And Synthesis

Chemical Properties

White solid

Synthesis Reference(s)

Tetrahedron, 61, p. 4569, 2005 DOI: 10.1016/j.tet.2005.03.008

Synthesis

1. Synthesis of 2-bromo-3-hydroxy-6-methylpyridine. To a 125 mL pyridine solution of 5-hydroxy-2-methylpyridine (8.80 g, 80.6 mmol) was slowly added dropwise 50 mL pyridine solution of bromine (14.18 g, 88.7 mmol). After the dropwise addition was completed, the temperature of the reaction mixture was raised to 40 °C. After 1 hour of reaction, the pyridine solvent was evaporated under reduced pressure. The resulting solid was suspended in 200 mL of water and stirred overnight. The solid product was collected by filtration and dried to give the target compound 2-bromo-3-hydroxy-6-methylpyridine as a brown solid (8.05 g, 53.1% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 2.21 (s, 3H), 6.73 (d, J = 8.1 Hz, 1H), 6.94 (d, J = 8.1 Hz, 1H), 9.36 (br s, 1H).

Structure and conformation

In the compound C6H6BrNO (2-Bromo-3-hydroxy-6-methylpyridine), the Br atom is displaced from the pyridine ring mean plane by 0.0948Å, while the hydroxyl O atom and the methyl C atom are displaced by 0.0173 and 0.015Å, respectively. In the crystal, mol-ecules are linked via O—H…N hydrogen bonds, forming chains propagating along the a-axis direction. These chains are linked by C—H?Br hydrogen bonds, forming corrugated two-dimensional networks lying parallel to the ac plane.

References

[1] Tetrahedron Letters, 1995, vol. 36, # 30, p. 5319 - 5322
[2] Patent: WO2011/133659, 2011, A2. Location in patent: Page/Page column 62-63
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8471 - 8489
[4] Tetrahedron, 2005, vol. 61, # 19, p. 4569 - 4576
[5] Patent: US2003/83357, 2003, A1

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