5-Bromo-2-chloro-3-nitropyridine Chemical Properties

Melting point:

65-70 °C

Boiling point:

285.4±35.0 °C(Predicted)

Density 

1.936±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

pka

-4.99±0.10(Predicted)

form 

Crystalline Powder

color 

Yellow

InChI

InChI=1S/C5H2BrClN2O2/c6-3-1-4(9(10)11)5(7)8-2-3/h1-2H

InChIKey

WWQQPSDIIVXFOX-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(Br)C=C1[N+]([O-])=O

CAS DataBase Reference

67443-38-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,T

Risk Statements 

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

Safety Statements 

37/39-26-45-36

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Bromo-2-chloro-3-nitropyridine Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

5-Bromo-2-chloro-3-nitropyridine is used as pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 2-chloro-3-nitro-5-bromopyridine from 2-amino-3-nitro-5-bromopyridine was as follows: 2-amino-5-bromo-3-nitropyridine (21.8 g, 0.1 mol) was ground in a mortar and pestle to a fine powder, which was subsequently suspended in 6 M hydrochloric acid (250 ml). The mixture was cooled to 0 °C and solid NaNO2 (8.3 g, 0.12 mol) was slowly added while keeping the internal temperature below 5 °C (about 45 min). After addition, stirring was continued at 0 °C for 1 hour. To the resulting suspension was added a solution of freshly prepared copper(I) chloride (12.9 g, 0.13 mol) dissolved in degassed 38% hydrochloric acid, and the reaction mass was gradually warmed up to room temperature over 90 min, and then subsequently heated up to 70°C to complete the decomposition of the diazonium salt. The reaction mixture was cooled, diluted with water (750 ml), passed through air for 30 min, and the pH was subsequently adjusted by the addition of 0.88 ammonia to about 9. The blue mixture was mixed with ether (600 ml) and shaken, and the insoluble solids were removed by filtration. The organic layer was washed sequentially with 5% ammonia, water, and brine and dried with anhydrous sodium sulfate. After filtration, the solution was pre-adsorbed onto silica and purified by fast chromatography using a gradient elution of isohexane with 5% to 20% ethyl acetate to afford 5-bromo-2-chloro-3-nitropyridine as a light yellow solid (13.1 g, 55% yield) and to recover the starting material (6.4 g). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.36 (1H, d, J=1Hz, H-6), 8.69 (1H, d, J=1Hz, H-4).

References

[1] Patent: WO2007/129044, 2007, A1. Location in patent: Page/Page column 77
[2] Patent: EP1214319, 2003, B1. Location in patent: Page/Page column 13
[3] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 2, p. 261 - 268
[4] Journal of the Chemical Society, 1952, p. 2042,2044
[5] Journal of the Chemical Society, 1952, p. 2042,2044

5-Bromo-2-chloro-3-nitropyridine(67443-38-3)Related Product Information

• 1-Hexadecylpyridinium bromide
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• 2-Chloro-3-nitropyridine
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• 2,3,5,6-Tetrachloropyridine
• 4-Chloro-3-nitropyridine
• 4-Nitrophenyl chloroformate
• 2-Chloro-3-fluoropyridine
• 3-AMINO-2-CHLORO-5-PICOLINE
• 2-Chloro-5-fluoronicotinonitrile
• 2-Chloro-3-pyridinamine
• 4-Bromo-2-chloro-3-iodopyridine
• 3-Amino-2-chloro-4-methylpyridine
• 5-Amino-2-chloro-3-picoline
• 2-CHLORO-3-FLUORO-4-IODOPYRIDINE
• 6-Bromo-2-chloro-3-iodopyridine
• 2-Chloro-3-methyl-5-nitropyridine
• 2-Chloro-3-methyl-5-bromopyridine