5-Fluoro-2-forMylpyridine Chemical Properties

Boiling point:

174℃

Density 

1.269

Flash point:

59℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

1.30±0.10(Predicted)

form 

solid

color 

White to yellow

InChI

InChI=1S/C6H4FNO/c7-5-1-2-6(4-9)8-3-5/h1-4H

InChIKey

IACCXWQKIQUVFQ-UHFFFAOYSA-N

SMILES

C1(C=O)=NC=C(F)C=C1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant

HS Code 

2933399990

5-Fluoro-2-forMylpyridine Usage And Synthesis

Uses

5-Fluoropyridine-2-aldehyde is a pyridine derivative with diverse chemical reactivity. It can undergo aromatic nucleophilic substitution, condensation, addition and other chemical reactions, and is mainly used as an intermediate in organic synthesis and a raw material for pharmaceutical chemicals.

Application

5-Fluoropyridine-2-aldehyde exhibits high chemical reactivity and is mainly used as an intermediate in organic synthesis and a raw material in pharmaceutical chemistry. It has certain applications in the synthesis of pyridine-based functional organic molecules. For example, some literature reports that this substance can be used in the preparation of pyridine-based antimalarial compounds.

Synthesis

The general procedure for the synthesis of 5-fluoropyridine-2-carboxylic acid from ethyl 5-fluoropyridine-2-carboxylate is as follows: 5-fluoropyridine-2-carboxylic acid (200 mg, 1.13 mmol) was reacted with ethanol (6 mL) and a dioxane solution of 4M HCl (0.5 mL) for 20 hours at 90°C. After completion of the reaction, the mixture was concentrated and mixed with saturated sodium carbonate solution and dichloromethane. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give ethyl 5-fluoropyridine-2-carboxylate (94 mg, 49.3% yield). Subsequently, ethyl 5-fluoropyridine-2-carboxylate (94 mg, 0.556 mmol) was dissolved in dichloromethane (4.0 mL) at room temperature, and a toluene solution of 1M DIBAL (1.23 mL, 1.23 mmol) was slowly added. The reaction mixture was stirred for 30 min, then the reaction was quenched with 2 M sodium carbonate solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product 5-fluoropyridine-2-carboxaldehyde (39 mg, 54.7% yield), which could be used directly in the subsequent reaction without further purification.GC-MS analysis showed a molecular ion peak (M+) of 125.

References

[1] Patent: WO2004/14902, 2004, A2. Location in patent: Page 42
[2] Patent: WO2009/58298, 2009, A1. Location in patent: Page/Page column 139
[3] Patent: WO2009/58299, 2009, A1. Location in patent: Page/Page column 55-56
[4] Patent: WO2010/111058, 2010, A1. Location in patent: Page/Page column 65
[5] Patent: WO2010/111059, 2010, A1. Location in patent: Page/Page column 50

5-Fluoro-2-forMylpyridine(31181-88-1)Related Product Information

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• 3,5-DIFLUOROPYRIDINE-2-CARBOXAMIDE
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