2-bromo-4-chloronicotinaldehyde

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2-bromo-4-chloronicotinaldehyde Basic information
Product Name:2-bromo-4-chloronicotinaldehyde
Synonyms:2-bromo-4-chloronicotinaldehyde;2-Bromo-4-chloropyridine-3-carboxaldehyde;2-Bromo-4-chloropyridine-3-carboxaldehyde 97%;2-bromo-4-chloropyridine-3-carbaldehyde;3-Pyridinecarboxaldehyde, 2-bromo-4-chloro-;2-Bromo-4-chloropyridine-4-carboxaldehyde
CAS:1289197-78-9
MF:C6H3BrClNO
MW:220.45
EINECS:
Product Categories:
Mol File:1289197-78-9.mol
2-bromo-4-chloronicotinaldehyde Structure
2-bromo-4-chloronicotinaldehyde Chemical Properties
Melting point 83-87°C
Boiling point 283.2±35.0 °C(Predicted)
density 1.800±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
form solid
pka-1.17±0.10(Predicted)
AppearanceOff-white to yellow Solid
InChIInChI=1S/C6H3BrClNO/c7-6-4(3-10)5(8)1-2-9-6/h1-3H
InChIKeyKCOAVFRTHTWKDO-UHFFFAOYSA-N
SMILESC1(Br)=NC=CC(Cl)=C1C=O
Safety Information
Hazard Codes T,Xi
Risk Statements 25-36
Safety Statements 26-45
RIDADR UN 2811 6.1 / PGIII
WGK Germany 3
HS Code 2933399990
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
Eye Irrit. 2
MSDS Information
2-bromo-4-chloronicotinaldehyde Usage And Synthesis
Synthesis
2-Bromo-4-chloropyridine

22918-01-0

N,N-Dimethylformamide

68-12-2

2-bromo-4-chloronicotinaldehyde

1289197-78-9

GENERAL STEPS: To an anhydrous tetrahydrofuran (40 mL) solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) was slowly added lithium diisopropylammonium solution (5.0 mL, 10.0 mmol, 2.0 M) over 5 minutes at -70 °C and stirring was continued for 1 hour at -70 °C. Subsequently, anhydrous N,N-dimethylformamide (1.3 g) was added dropwise over 3 minutes and the reaction mixture was stirred at the same temperature for another 30 minutes. After completion of the reaction, the reaction was quenched with saturated ammonium chloride solution (30 mL) and extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (20:1) as eluent to afford 2-bromo-4-chloropyridine-3-carboxaldehyde (114a) as a yellow solid (900 mg, 48% yield).1H NMR (500 MHz, DMSO) δ 10.21 (s, 1H), 8.52 (d, J = 5.5 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H).

References[1] Patent: US2013/116262, 2013, A1. Location in patent: Paragraph 0307
[2] Patent: EP2773638, 2015, B1. Location in patent: Paragraph 0185
[3] Patent: US2013/116246, 2013, A1. Location in patent: Paragraph 0246
2-bromo-4-chloronicotinaldehyde Preparation Products And Raw materials
Raw materials2-Bromo-4-chloropyridine-->N,N-Dimethylformamide-->Lithium diisopropylamide-->Tetrahydrofuran
Tag:2-bromo-4-chloronicotinaldehyde(1289197-78-9) Related Product Information
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