Pyridine, 5-(bromomethyl)-2-chloro- (9CI) Chemical Properties

Melting point:

48-50°C

Boiling point:

262.5±25.0 °C(Predicted)

Density 

1.663±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-0.89±0.10(Predicted)

form 

Solid

color 

Pale Yellow

InChI

InChI=1S/C6H5BrClN/c7-3-5-1-2-6(8)9-4-5/h1-2,4H,3H2

InChIKey

YJOULMMJZAADRY-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(CBr)C=C1

Safety Information

RIDADR 

1759

HazardClass 

8

PackingGroup 

Ⅲ

Pyridine, 5-(bromomethyl)-2-chloro- (9CI) Usage And Synthesis

Uses

5-Bromomethyl-2-chloropyridine is a reagent used in the preparation of gonadotropin-releasing hormone receptor antagonist using uracil scaffold.

Synthesis

The general procedure for the synthesis of 5-bromomethyl-2-chloropyridine using 2-chloro-5-methylpyrimidine as starting material was as follows: synthetic embodiment 25, N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (compound 243). 2-Chloro-5-methylpyrimidine (1.04 g, 8.13 mmol) was dissolved in 30 mL of carbon tetrachloride and N-bromosuccinimide (1.73 g, 9.75 mmol) and benzoyl peroxide (20 mg) were added. The mixture was heated to reflux for 6 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 3:1) to afford 5-bromomethyl-2-chloropyridine 641 mg (38% yield).1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 8.66 (2H, s).

References

[1] Patent: US2013/150414, 2013, A1. Location in patent: Paragraph 0437

Pyridine, 5-(bromomethyl)-2-chloro- (9CI)(182924-36-3)Related Product Information

• 3-(Bromomethyl)pyridine
• Pyridine, 5-(bromomethyl)-2-chloro- (9CI)