2,3-DIBROMO-5-METHYLPYRIDINE Chemical Properties

Melting point:

53.0 to 57.0 °C

Boiling point:

270.8±35.0 °C(Predicted)

Density 

1.911±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

-1.27±0.20(Predicted)

color 

White to Light yellow to Light orange

CAS DataBase Reference

29232-39-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

20/21/22-36/37/38-41-25

Safety Statements 

26-36/37/39-45-39

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

2,3-DIBROMO-5-METHYLPYRIDINE Usage And Synthesis

Synthesis

2-Amino-3-bromo-5-methylpyridine (187 mg, 1.00 mmol) was added to a 30 mL three-necked flask, followed by the addition of 48% aqueous hydrogen bromide (1 mL) to dissolve the feedstock. The reaction mixture was cooled in an ice bath, keeping the internal temperature in the range of 2 to 5 °C, and bromine (154 μL, 3.00 mmol) was slowly added dropwise. After the dropwise addition, stirring was continued at the same temperature for 10 min. Subsequently, a solution of sodium nitrite (174 mg, 2.5 mmol) dissolved in water (500 μL) was added dropwise to the reaction system while keeping the temperature unchanged, and stirring was continued for 1 h after completion of the dropwise addition. After completion of the reaction, a solution of sodium hydroxide (377 mg, 9.4 mmol) dissolved in water (2 mL) was added slowly and the mixture was stirred for 1 h at room temperature. The reaction solution was transferred to a partition funnel and separated by extraction with ethyl acetate (10 mL) and water (10 mL), and the aqueous phase was extracted once more with ethyl acetate (10 mL). The organic phases were combined and washed sequentially with 5% aqueous sodium sulfite (5 mL) and saturated saline (10 mL), then dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to afford the target product 2,3-dibromo-5-methylpyridine (244 mg, 0.97 mmol) as a yellow solid in 97% yield. The product was analyzed by 1H-NMR (CDCl3, TMS, 300 MHz) δ (ppm): 2.30 (s, 3H), 7.73 (d, 1H, J = 1.5 Hz), 8.14 (d, 1H, J = 1.2 Hz); 13C-NMR (CDCl3, TMS, 300 MHz) δ (ppm): 17.41, 123.16. 134.13, 140.39, 142.29, 148.57; high-resolution mass spectrometry (C6H5Br2N) Theoretical: [M+] 248.8789, Measured: [M+] 248.8786; Melting point 54.2 °C.

References

[1] Patent: WO2008/16184, 2008, A1. Location in patent: Page/Page column 187-188

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