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

Melting point:

60-65°C

Boiling point:

296.9±25.0 °C(Predicted)

Density 

1.955

storage temp. 

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

solubility 

Chloroform (Soluble), Methanol (Slightly)

form 

Solid

pka

-0.12±0.10(Predicted)

color 

White to Pale Yellow

InChIKey

CRRMIKBAPPOPNW-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

RIDADR 

UN 3335

WGK Germany 

3

HS Code 

2933399990

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

Uses

2-Bromo-5-(bromomethyl)pyridine is a useful research chemical compound used in the synthesis of methyleneimidazole substituted biaryls as inhibitors of human 17α-hydroxylase-17,20-lyase.

Synthesis

General procedure for the synthesis of 2-bromo-5-(bromomethyl)pyridine from 2-bromo-5-methylpyridine: 1. dissolve 12 g (70 mmol) of 2-bromo-5-methylpyridine in 100 mL of 1,2-dichloroethane. 2. 16 g (91 mmol) of N-bromosuccinimide and 0.40 g (2.4 mmol) of 2,2'-azobis(isobutyronitrile) were added to the above solution. 3. The reaction mixture was stirred at 85 °C for 15 min. 4. Upon completion of the reaction, water was added to the reaction mixture and the organic layer was separated. 5. The organic layer was dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum. 6. The resulting residue was purified by silica gel column chromatography with an eluent ratio of solvent-free hexane:ethyl acetate = 10:1 to 9:1 (v/v). 7. The fraction containing the target compound was collected and concentrated in vacuo to give 15 g of 2-bromo-5-(bromomethyl)pyridine as white powder in 89% yield. 8. 8. The Rf value of the product was 0.63 (n-hexane:ethyl acetate=9:1, v/v). 9. Mass spectrum (CI, m/z): 250, 252, 254 (M++1). 10. 10. 1H-NMR spectrum (CDCl3, δ ppm): 4.42 (s, 2H), 7.49 (d, J=8.3 Hz, 1H), 7.61 (dd, J1=8.3 Hz, J2=2.7 Hz, 1H), 8.39 (d, J=2.7 Hz, 1H).

References

[1] Patent: EP1679308, 2006, A1. Location in patent: Page/Page column 35
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1992 - 2010
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 2 - 6
[4] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 559 - 564
[5] Patent: WO2012/52540, 2012, A1. Location in patent: Page/Page column 47; 48-49

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