| Identification | Back Directory | [Name]
4-AMINO-3,5-DIBROMOPYRIDINE | [CAS]
84539-34-4 | [Synonyms]
AURORA 15013
IFLAB-BB F1371-0141
OTAVA-BB BB7110951384
3,5-DIBROMOPYRIDIN-4-AMINE
3,5-dibroMo-4-aMinopyridin
4-aMino-3,5-dibroMopyridin
3,5-Dibromo-4-pyridinamine
3,5-dibromo-4-aminopyridine
4-AMINO-3,5-DIBROMOPYRIDINE
4-Pyridinamine, 3,5-dibromo-
3,5-Dibromo-pyridin-4-ylamine
Dalfampridine Related Compound B
4-AMINO-3,5-DIBROMOPYRIDINE ISO 9001：2015 REACH
4-Amino-3,5-dibromopyridine
3,5-Dibromopyridin-4-amine | [Molecular Formula]
C5H4Br2N2 | [MDL Number]
MFCD00234048 | [MOL File]
84539-34-4.mol | [Molecular Weight]
251.91 |
| Chemical Properties | Back Directory | [Melting point ]
156-158℃ | [Boiling point ]
292.9±35.0 °C(Predicted) | [density ]
2.147 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
4.96±0.24(Predicted) | [color ]
Light yellow to Yellow to Orange |
| Hazard Information | Back Directory | [Chemical Properties]
white solid | [Uses]
4-Amino-3,5-dibromopyridine is an important synthetic intermediate of a natural product Desmopyradine, can be converted into another important pyridine intermediate such as 3, 5-dibromopyridine, 3, 5-dibromo-4-iodopyridine and the like, and has important synthetic value. | [Preparation]
A preparation method of 4-Amino-3,5-dibromopyridine is characterized by comprising the following steps: pyridine or pyridine salt is taken as raw material, ammonium salt and H are added into HBr solution2O2And reacting in one step to obtain the 4-Amino-3,5-dibromopyridine.
| [Synthesis]
General procedure for the synthesis of 4-amino-3,5-dibromopyridine from 4-aminopyridine: To a suspension of 4-aminopyridine (188.2 mg, 2.0 mmol, 1.0 eq.) in dichloromethane (10 mL) was added slowly over a period of 1 hour a dichloromethane (30 mL) solution of N-bromosuccinimide (818.7 mg, 4.6 mmol, 2.3 eq.). ) solution. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a mixture of succinimide and 4-amino-3,5-dibromopyridine. The mixture was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1/1) to afford the target product 4-amino-3,5-dibromopyridine (464.8 mg, 1.84 mmol, 92% yield) as a colorless solid. Thin layer chromatography (TLC) Rf value was 0.62 (unfolding agent: hexane/ethyl acetate = 1/1). The melting point is 163-167 °C. Infrared spectrum (KBr, cm^-1): 3535, 3429, 3266, 3100, 2667, 2536, 2329, 1872, 1825, 1785, 1626, 1566, 1522, 1485, 1408, 1323, 1262, 1154, 1138, 1081, 1051, 892, 855. 747, 726, 658, 589, 573, 517, 468, 431.NMR hydrogen spectrum (300 MHz, CDCl3) δ 8.31 (2H, s, H2/6), 5.06 (2H, s, NH). NMR carbon spectra (75 MHz, CDCl3) δ 149.9, 147.8, 106.2. electron bombardment mass spectra (EI-MS) m/z calculated value C5H4Br2N2 [M]+ 249.87, measured value 249.90. | [References]
[1] Synthesis, 2001, # 14, p. 2175 - 2179
[2] Chemistry - A European Journal, 2012, vol. 18, # 20, p. 6328 - 6334
[3] Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1557 - 1563
[4] Patent: CN106957259, 2017, A. Location in patent: Paragraph 0015; 0017; 0019
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4575 - 4578 |
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