2,5-Dibromo-3-methylpyridine Chemical Properties

Melting point:

43-47 °C (lit.)

Boiling point:

114 °C / 6mmHg

Density 

1.9318 (rough estimate)

refractive index 

1.6300 (estimate)

Flash point:

>230 °F

storage temp. 

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

solubility 

soluble in Methanol

pka

-1.27±0.20(Predicted)

form 

Crystalline Powder

color 

Off-white to beige

InChI

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

InChIKey

LIMXEVCFAUTBCK-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C(Br)C=C1C

CAS DataBase Reference

3430-18-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

26-36/37/39-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2,5-Dibromo-3-methylpyridine Usage And Synthesis

Uses

2,5-Dibromo-3-methylpyridine is a pyridine organic compound, mainly used as a pharmaceutical intermediate.

Chemical Properties

Off-white to beige crystalline powder

Synthesis

General procedure for the synthesis of 2,5-dibromo-3-methylpyridine (49) from 2-amino-3-methyl-5-bromopyridine (48, 69 g, 0.37 mol): the raw material was suspended in hydrobromic acid (200 mL, 48% aqueous solution) and cooled to -15 °C. The reaction was carried out in aqueous solution of sodium nitrite (100 mL). Bromine (95 g, 0.59 mol) was slowly added dropwise, followed by an aqueous solution (100 mL) of sodium nitrite (69 g, 1 mol), while keeping the temperature of the reaction mixture below -15 °C. The reaction mixture was then cooled to -15 °C. After completion of the dropwise addition, the cooling bath was removed and the reaction mixture was stirred for 3 hours at room temperature. The reaction was cooled again to -15 °C and quenched with an aqueous solution (500 mL) of potassium hydroxide (112 g, 2 mol). After removing the cooling bath, stirring was continued for 1.5 hours. The product was extracted with ethyl acetate (3 x 300 mL), the organic phases were combined, washed sequentially with water (2 x 200 mL), saturated aqueous sodium bicarbonate (200 mL), dried over sodium sulfate and concentrated to dryness under reduced pressure. The oily residue was dissolved in chloroform (100 mL), filtered through a silica gel pad and washed with chloroform. The filtrates were combined and evaporated under reduced pressure to give the light yellow solid product 49 (87 g, 94%) with a melting point of 38-40 °C (literature value: 41-42 °C). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) δ 8.22 (d, J = 2.4 Hz, 1H), 7.61 (d, J = 2.4 Hz, 1H), 2.33 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 148.29, 143.05, 141.15, 137.15, 119.68, 22.06 Confirmed.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1682 - 1697
[2] Patent: US2014/18360, 2014, A1. Location in patent: Paragraph 0175
[3] Patent: CN105348177, 2016, A. Location in patent: Paragraph 0012; 0017
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1129 - 1131
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3730 - 3742

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