2,5-DIBROMO-6-METHYLPYRIDINE Chemical Properties

Melting point:

0°C

Boiling point:

0°C

Density 

1.911±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

-0.84±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C6H5Br2N/c1-4-5(7)2-3-6(8)9-4/h2-3H,1H3

InChIKey

UCHKRHGVKYVGTC-UHFFFAOYSA-N

SMILES

C1(C)=NC(Br)=CC=C1Br

CAS DataBase Reference

39919-65-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-41-22

Safety Statements 

26-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29333990

2,5-DIBROMO-6-METHYLPYRIDINE Usage And Synthesis

Chemical Properties

white to light yellow solid

Uses

2,5-Dibromo-6-methylpyridine is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

5-Bromo-2-amino-6-methylpyridine hydrobromide (29.4 kg, purity 76.5 wt%, 84 mol, 1.00 eq.) was dissolved in 48% hydrobromic acid (162.0 kg, 961 mol, 11.44 eq.) at a temperature below 35 °C. The resulting solution was cooled to 2 °C and bromine (43.0 kg, 269 mol, 3.20 eq.) was slowly added over 40 min. Subsequently, a 40 wt% aqueous sodium nitrite solution (28.9 kg, 419 mol, 4.99 eq.) was added dropwise over 50 min at a temperature range of -1 to 5 °C. The reaction mixture was kept at this temperature for 1 h. The pH was then adjusted to 13.1 with 50% aqueous sodium hydroxide solution (120.0 kg). the reaction solution was slowly warmed to 20 °C over 1 h and toluene (78.0 kg) was added. The mixture was stirred for 30 minutes and left to stand overnight. The clarified organic phase was obtained by filtration and washed twice with saturated aqueous sodium chloride solution (51.1 kg). A final 96.0 kg solution of 2,5-dibromo-6-methylpyridine (concentration 17.3 wt%) was obtained in 79% yield.

References

[1] Patent: WO2005/51954, 2005, A2. Location in patent: Page/Page column 38; 39

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