2-FLUORO-3-FORMYLPYRIDINE Chemical Properties

Boiling point:

50 °C/3 mmHg

Density 

1.250 g/mL at 25 °C

refractive index 

n20/D 1.520

Flash point:

164 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-2.23±0.10(Predicted)

form 

liquid

color 

Clear, dark yellow

InChIKey

OFBVGDCXXGXDKU-UHFFFAOYSA-N

CAS DataBase Reference

36404-90-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich

2-FLUORO-3-FORMYLPYRIDINE Usage And Synthesis

Uses

Attachment of isoxazolinones by displacement of fluoride provide naphthyridines on hydrogenolysis and cyclization.

Synthesis

GENERAL STEPS: Lithium (trimethylsilylmethyl) (22 mL, 13.8 wt% hexane solution) was added to a 100 mL three-necked round-bottomed flask and the reaction system cooled to -50 °C. A mixed solution containing 2-fluoropyridine (2.0 g), THF (25 mL), and diisopropylamine (0.13 mL) was slowly added over 1 min while keeping the temperature below -50 °C. After 3 hours of reaction, 1-formylpiperidine (2.4 g) was added over 1 min, also at below -50 °C. Subsequently, the reaction mixture was gradually warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction was quenched with acetic acid (3 mL) and water (7 mL). The aqueous layer was separated and washed with methyl tert-butyl ether (MTBE, 3 x 25 mL). All organic layers were combined, dried with anhydrous magnesium sulfate (MgSO?) and concentrated under reduced pressure to give 3.79 g of brown oil. Finally, the oily material was purified by silica gel column chromatography, using a hexane solution of 15% ethyl acetate as eluent, to give 2.24 g of 2-fluoro-3-pyridinecarboxaldehyde with a purity of 92.4% (90% yield, corrected for assay).

References

[1] Patent: WO2004/92125, 2004, A2. Location in patent: Page 7-8
[2] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56

2-FLUORO-3-FORMYLPYRIDINE(36404-90-7)Related Product Information

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