Identification | Back Directory | [Name]
4-AMINO-5-BROMO-3-METHYLPYRIDINE | [CAS]
97944-43-9 | [Synonyms]
4-AMINO-5-BROMO-3-PICOLINE 3-Bromo-5-methylpyridin-4-amine 3-Bromo-5-methyl-4-pyridinamine 4-AMINO-5-BROMO-3-METHYLPYRIDINE 4-Pyridinamine, 3-bromo-5-methyl- 3-Bromo-5-methyl-pyridin-4-ylamine 4-Amino-5-bromo-3-methylpyridine 95+% 4-AMINO-5-BROMO-3-METHYLPYRIDINE ISO 9001:2015 REACH | [Molecular Formula]
C6H7BrN2 | [MDL Number]
MFCD07437841 | [MOL File]
97944-43-9.mol | [Molecular Weight]
187.04 |
Chemical Properties | Back Directory | [Melting point ]
115.0 °C | [Boiling point ]
290.0±35.0 °C(Predicted) | [density ]
1.593±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
7.34±0.24(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C6H7BrN2/c1-4-2-9-3-5(7)6(4)8/h2-3H,1H3,(H2,8,9) | [InChIKey]
GUAFGBUKLIFASX-UHFFFAOYSA-N | [SMILES]
C1=NC=C(C)C(N)=C1Br |
Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 3-methyl-4-amino-5-bromopyridine from 3-methyl-4-aminopyridine is as follows:
Step 1: To a solution of 4-amino-3-methylpyridine (97, 10 g, 0.092 mol) and hydrobromic acid (HBr, 50 mL) heated to 70 °C was slowly added 15% hydrogen peroxide (H2O2, 16 mL) over a period of 1 hour. The reaction mixture was continued to be stirred at 70 °C for 1 h. The reaction was subsequently quenched by pouring into ice (100 g). The pH of the reaction mixture was adjusted to about 5 with 50% sodium hydroxide (NaOH) solution and the resulting red precipitate was collected by filtration. Subsequently, the pH of the filtrate was adjusted to about 9 and the resulting white precipitate was collected by filtration to afford 3-methyl-4-amino-5-bromopyridine (98, 13.5 g, 78% yield). | [References]
[1] Patent: WO2005/16892, 2005, A1. Location in patent: Page/Page column 104 [2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374 [3] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374 [4] Patent: US2013/5705, 2013, A1 |
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