| Identification | Back Directory | [Name]
2-Amino-3-bromo-5-cyanopyridine | [CAS]
477871-32-2 | [Synonyms]
2-Amino-3-bromo-5-cyanopyridine
3-Pyridinecarbonitrile, 6-amino-5-bromo-
2-Amino-3-bromo-5-cyanopyridine ISO 9001：2015 REACH | [Molecular Formula]
C6H4BrN3 | [MDL Number]
MFCD02102412 | [MOL File]
477871-32-2.mol | [Molecular Weight]
198.02 |
| Chemical Properties | Back Directory | [Melting point ]
194-195° | [Boiling point ]
294.4±40.0 °C(Predicted) | [density ]
1.80±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
solid | [pka]
0.72±0.49(Predicted) | [color ]
Beige | [InChI]
InChI=1S/C6H4BrN3/c7-5-1-4(2-8)3-10-6(5)9/h1,3H,(H2,9,10) | [InChIKey]
CKUQTHSGTPGGFK-UHFFFAOYSA-N | [SMILES]
C1=NC(N)=C(Br)C=C1C#N |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 6-amino-5-bromonicotinonitrile from 2-amino-5-cyanopyridine is as follows:
Step 1: To a solution of 6-aminonicotinonitrile (102 mg, 0.86 mmol) in acetic acid (2 mL) was added a solution of bromine in acetic acid (0.86 mmol). The mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by rapid chromatography on silica gel (eluent: hexane/ethyl acetate, 3:1, v/v) to afford the title compound 6-amino-5-bromonicotinonitrile (110 mg, 65% yield).
The product characterization data are as follows:
1H-NMR (DMSO, 300 MHz): δ 8.26 (d, 1H, J = 2.0 Hz), 8.10 (d, 1H, J = 2.0 Hz), 7.24 (bs, 2H).
MS (APCI Neg): m/z 196, 198. | [References]
[1] Patent: WO2005/90337, 2005, A1. Location in patent: Page/Page column 42-43
[2] Patent: WO2008/60907, 2008, A2. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 9, p. 2073 - 2078
[4] Patent: US2015/266872, 2015, A1. Location in patent: Paragraph 0783; 0784
[5] Patent: EP3372601, 2018, A1. Location in patent: Paragraph 0743; 0744 |
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