| Identification | More | [Name]
2-Bromo-3-methyl-5-nitropyridine | [CAS]
23132-21-0 | [Synonyms]
2-BROMO-3-METHYL-5-NITROPYRIDINE
2-BROMO-5-NITRO-3-PICOLINE
2-Hydorxy-5-Nitro-3-Picoline
2-HYDROXY-5-NITRO-3-PICOLINE (2-HYDROXY-3-METHYL-5-NITROPYRIDINE) | [EINECS(EC#)]
677-832-1 | [Molecular Formula]
C6H5BrN2O2 | [MDL Number]
MFCD03095065 | [Molecular Weight]
217.02 | [MOL File]
23132-21-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
57-58°C | [Boiling point ]
305.1±37.0 °C(Predicted) | [density ]
1.709±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [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 |
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