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4-Chloropicolinaldehyde

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4-Chloropicolinaldehyde Basic information
Product Name:4-Chloropicolinaldehyde
Synonyms:4-CHLOROPYRIDINE-2-CARBOXALDEHYDE;4-chloro-2-pyridinecarbaldehyde;4-Chloropyridin-2-ylcarboxaldehyde;2-Pyridinecarboxaldehyde,4-chloro-;Picolinaldehyde, 4-chloro-;4-chloropyridine-2-carbaldehyde;oropyridine-2-carbaL;4-CHLOROPICOLINALDEHYDE ISO 9001:2015 REACH
CAS:63071-13-6
MF:C6H4ClNO
MW:141.56
EINECS:
Product Categories:Pyridines
Mol File:63071-13-6.mol
4-Chloropicolinaldehyde Structure
4-Chloropicolinaldehyde Chemical Properties
Melting point 32-34°
Boiling point 206℃
density 1.332
Fp 79℃
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility Chloroform (Slightly), Methanol (Slightly)
pka1.78±0.10(Predicted)
form Solid
color Off-White to Pale Yellow
Stability:Air Sensitive
Safety Information
Risk Statements 43
Safety Statements 36/37
HazardClass IRRITANT
HS Code 2933399990
MSDS Information
4-Chloropicolinaldehyde Usage And Synthesis
Uses4-Chloro-2-pyridinecarboxaldehyde is a useful synthetic intermediate. It is used in the synthesis of 2,2''-bipyridines, (chloropyridyl)(pyridyl)ethylamine and aryl and heteroaryl fluoromethyl ketones.
Synthesis
Methyl 4-chloropicolinate

24484-93-3

4-CHLOROPICOLINALDEHYDE

63071-13-6

General procedure for the synthesis of 4-chloro-2-pyridinecarboxaldehyde from methyl 4-chloropyridinecarboxylate: to a solution of methyl 4-chloropyridinecarboxylate (2.5 g, 14.6 mmol) in anhydrous THF (100 mL) was added slowly and dropwise diisobutylaluminum hydride (1.0 M solution in THF, 29.1 mmol) at -78 °C and the reaction was stirred in an argon atmosphere at that temperature mixture for 2 hours. Upon completion of the reaction, the reaction was quenched with methanol (MeOH) at -78 °C, followed by the addition of potassium sodium tartrate solution (1.0 M, 180 mL), and the mixture was stirred and gradually warmed to room temperature over a period of 1 hour. The reaction mixture was diluted with ethyl acetate (EtOAc, 60 mL) and the organic layer was separated, washed with saturated saline and dried with anhydrous sodium sulfate. The solvent was removed by mild decompression distillation at room temperature to afford the target product 4-chloro-2-pyridinecarboxaldehyde (1.87 g, 91% yield), which solidified to light yellow crystals after standing at room temperature.

References[1] Patent: US2004/186114, 2004, A1. Location in patent: Page/Page column 69; 70
[2] Patent: EP1897880, 2008, A1. Location in patent: Page/Page column 16
[3] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[4] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
4-Chloropicolinaldehyde Preparation Products And Raw materials
Raw materialsMethyl 4-chloropicolinate-->(4-Chloro-pyridin-2-yl)-methanol-->Diisobutylaluminium hydride-->Tetrahydrofuran-->Methanol-->Potassium sodium tartrate
Tag:4-Chloropicolinaldehyde(63071-13-6) Related Product Information
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