2-Bromo-3-methyl-5-nitropyridine

2-Bromo-3-methyl-5-nitropyridine Property

Melting point:

57-58°C

Boiling point:

305.1±37.0 °C(Predicted)

Density 

1.709±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

pka

-2.95±0.20(Predicted)

Appearance

Light yellow to yellow Solid

BRN 

1565441

InChI

InChI=1S/C6H5BrN2O2/c1-4-2-5(9(10)11)3-8-6(4)7/h2-3H,1H3

InChIKey

FZIQHPKXSLHGBZ-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C([N+]([O-])=O)C=C1C

CAS DataBase Reference

23132-21-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-21/22

Safety Statements 

26-36-36/37

HazardClass 

IRRITANT

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Bromo-3-methyl-5-nitropyridine Chemical Properties,Usage,Production

Chemical Properties

off-white solid

Synthesis

General procedure for the synthesis of 2-bromo-5-nitro-3-methylpyridine from 3-methyl-5-nitropyridin-2(1H)-one: Synthesis of common intermediates of Scheme 4 Step 1: Synthesis of 2-bromo-3-(bromomethyl)-5-nitropyridine (Scheme 4, compound 27) A sample of 3-methyl-5-nitropyridin-2-ol (1.44 g, 9.34 mmol) was placed in a 35 mL pressure vessel and dissolved in a solvent mixture of toluene/DMF (10:1 v/v; 15 mL). The container was sealed with a septum, and after argon replacement, phosphorus tribromide (1.32 mL, 14.0 mmol) was added via syringe. The septum was replaced with a polytetrafluoroethylene cap and the mixture was stirred at 120°C for 20 minutes. Upon completion of the reaction, the mixture was cooled to room temperature, neutralized with 3M NaOH solution, and extracted with toluene (3 x 15 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated in vacuum to give 2.00 g of the target product 2-bromo-3-methyl-5-nitropyridine as an orange solid in 99% yield. 1H NMR (400MHz, CDCl3) δ 9.04 (d, J = 2.7Hz, 1H), 8.29 (d, J = 2.5Hz, 1H), 2.54 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 150.65, 142.47, 136.76, 132.75, 22.20.

References

[1] Patent: WO2011/147038, 2011, A1. Location in patent: Page/Page column 57