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2-Bromo-5-chloro-3-fluoropyridine

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2-Bromo-5-chloro-3-fluoropyridine manufacturers

2-Bromo-5-chloro-3-fluoropyridine Basic information
Product Name:2-Bromo-5-chloro-3-fluoropyridine
Synonyms:2-Bromo-5-chloro-3-fluoropyridine;2-Bromo-3-fluoro-5-chloropyridine;Pyridine, 2-bromo-5-chloro-3-fluoro-;2-Bromo-5-chloro-3-fluoropyridine ISO 9001:2015 REACH
CAS:514797-97-8
MF:C5H2BrClFN
MW:210.43
EINECS:
Product Categories:Halides;Heterocycles
Mol File:514797-97-8.mol
2-Bromo-5-chloro-3-fluoropyridine Structure
2-Bromo-5-chloro-3-fluoropyridine Chemical Properties
Boiling point 190.8±35.0 °C(Predicted)
density 1.829±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-3.92±0.20(Predicted)
form solid
color White to off-white
InChIInChI=1S/C5H2BrClFN/c6-5-4(8)1-3(7)2-9-5/h1-2H
InChIKeyPYDGFYYLQFJQBZ-UHFFFAOYSA-N
SMILESC1(Br)=NC=C(Cl)C=C1F
Safety Information
RIDADR UN2811
HS Code 2933399990
MSDS Information
2-Bromo-5-chloro-3-fluoropyridine Usage And Synthesis
Synthesis
2-Amino-5-chloro-3-fluoropyridine

246847-98-3

2-Bromo-5-chloro-3-fluoropyridine

514797-97-8

Step 1: 2-Amino-3-fluoro-5-chloropyridine (5.0 g, 34 mmol) was slowly added to 48% hydrobromic acid (HBr) solution (20 mL) at 0°C with stirring. Bromine (Br2, 5.24 mL, 102.3 mmol) was then added dropwise to the resulting mixture over 20 min at 0 °C. The reaction mixture was cooled to -10°C. A solution of sodium nitrite (NaNO2, 5.88 g, 85.3 mmol) in water (20 mL) was slowly added to the mixture over a period of 1.5 h and the mixture continued to be stirred for 30 min. Subsequently, a solution of sodium hydroxide (NaOH, 12 g, 306 mmol) in water (20 mL) was added over 30 minutes and the mixture was gradually warmed to room temperature. After completion of the reaction, the mixture was extracted with ether (3 x 100 mL). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound 2-bromo-5-chloro-3-fluoropyridine as a pale yellow solid (6.43 g, 90% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.23 (d, J = 2.1 Hz, 1H), 7.48 (dd, J = 7.1,2.1 Hz, 1H).

References[1] Patent: WO2015/187845, 2015, A1. Location in patent: Paragraph 0218
[2] Patent: WO2016/44323, 2016, A1. Location in patent: Paragraph 0323
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