2-Amino-5-bromo-3-(hydroxymethyl)pyridine Chemical Properties

Melting point:

137-140°C

Boiling point:

343.5±37.0 °C(Predicted)

Density 

1.766±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Acetone, Ethyl Acetate, Methanol

pka

13.16±0.10(Predicted)

form 

Solid

color 

Off-white to yellow

InChI

InChI=1S/C6H7BrN2O/c7-5-1-4(3-10)6(8)9-2-5/h1-2,10H,3H2,(H2,8,9)

InChIKey

HIVQAWXDBPYNDU-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1CO

CAS DataBase Reference

335031-01-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

2-Amino-5-bromo-3-(hydroxymethyl)pyridine Usage And Synthesis

Uses

2-Amino-5-bromo-3-(hydroxymethyl)pyridine can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

2-Amino-5-bromo-3-(hydroxymethyl)pyridineBromine (8.4 mL, 189.4 mmol) was added dropwise over 1 hour to a solution of 2- amino-3-(hydroxymethyl)pyridine (19.6 g, 157.8 mmol) in acetic acid (350 mL) at room temperature. The reaction mixture was then stirred overnight. After concentration to dryness, the residue was partitioned between a saturated solution of potassium carbonate (300 mL) and ethyl acetate (200 ml_). The aqueous layer was separated and extracted with ethyl acetate (2 x 200 ml_). The combined organic phases were washed with a saturated solution of sodium chloride (200 ml_), dried over sodium sulfate, filtered and concentrated to dryness. After trituration of the residue in pentane, the title product was obtained as a yellow solid (27.0 g, 84%).

References

[1] Patent: WO2011/61214, 2011, A1. Location in patent: Page/Page column 30-31
[2] Patent: EP1226138, 2004, B1
[3] Patent: US2004/53814, 2004, A1
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1627 - 1635
[5] Patent: CN108440523, 2018, A. Location in patent: Paragraph 0028; 0030

2-Amino-5-bromo-3-(hydroxymethyl)pyridine(335031-01-1)Related Product Information

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