| Identification | Back Directory | [Name]
4-AMINO-3-BROMO-2-CHLOROPYRIDINE | [CAS]
215364-85-5 | [Synonyms]
SA037434
3-Bromo-2-chloro-4-pyridinamine
3-broMo-2-chloropyridin-4-aMine
4-AMINO-3-BROMO-2-CHLOROPYRIDINE
4-PyridinaMine,3-broMo-2-chloro-
3-BroMo-2-chloro-pyridin-4-ylaMine
4-AMino-3-broMo-2-chloropyridine, 97+%
4-AMINO-3-BROMO-2-CHLOROPYRIDINE ISO 9001：2015 REACH | [EINECS(EC#)]
694-576-6 | [Molecular Formula]
C5H4BrClN2 | [MDL Number]
MFCD09263478 | [MOL File]
215364-85-5.mol | [Molecular Weight]
207.456 |
| Chemical Properties | Back Directory | [Melting point ]
150-151° | [Boiling point ]
329.0±37.0 °C(Predicted) | [density ]
1.834±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
2.73±0.42(Predicted) | [Appearance]
White to off-white Solid | [Sensitive ]
Air Sensitive | [InChI]
InChI=1S/C5H4BrClN2/c6-4-3(8)1-2-9-5(4)7/h1-2H,(H2,8,9) | [InChIKey]
KTWAUKYSQFZIET-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC(N)=C1Br |
| Hazard Information | Back Directory | [Uses]
4-Amino-3-bromo-2-chloropyridine is an organic compound, which is often used as a synthetic intermediate for certain drugs, including peptide drugs, hormone drugs, anti-tumor drugs, etc. It is also used in the synthesis of dyes. | [Synthesis]
General procedure for the synthesis of 3-bromo-2-chloropyridin-4-amine from 2-chloro-4-aminopyridine: N-bromosuccinimide (NBS, 2.77 g, 15.56 mmol) was added batchwise to a stirred solution of 2-chloropyridin-4-amine (17A, 2 g, 15.56 mmol) in acetic acid (20 mL) at 0 °C and under nitrogen protection. The reaction mixture was then stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and azeotropic distillation with ethanol was performed to further remove the residual solvent. The crude product was purified by silica gel column chromatography (using a 40 g RediSep column with a gradient elution using a petroleum ether solution of 10-20% ethyl acetate as eluent) to afford the target compound, 3-bromo-2-chloropyridin-4-amine (15B, 2 g, 9.64 mmol, 62.0% yield), as a white solid.LCMS analysis: m/z = 209.0 [M + H]+; retention time 0.84 min; condition B. | [References]
[1] Patent: WO2016/133838, 2016, A1. Location in patent: Paragraph 0315
[2] Patent: US2016/16951, 2016, A1. Location in patent: Paragraph 0878; 0879
[3] Patent: WO2008/8539, 2008, A2. Location in patent: Page/Page column 133
[4] Patent: US2014/336182, 2014, A1. Location in patent: Paragraph 0306-0307
[5] Patent: WO2008/124083, 2008, A2. Location in patent: Page/Page column 47 |
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