2-CHLORO-4-FLUORONICOTINIC ACID Chemical Properties

Boiling point:

302.1±37.0 °C(Predicted)

Density 

1.576±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.46±0.25(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C6H3ClFNO2/c7-5-4(6(10)11)3(8)1-2-9-5/h1-2H,(H,10,11)

InChIKey

GXDFQGOVWALHAS-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(F)=C1C(O)=O

Safety Information

HS Code 

2933399990

2-CHLORO-4-FLUORONICOTINIC ACID Usage And Synthesis

Application

2-Chloro-4-fluoronicotinic acid is a carboxylic acid derivative that can be used to prepare glucocorticoid receptor ligands.

Synthesis

Step A: Synthesis of 2-chloro-4-iodopyridine-3-carboxylic acid (64-2) 1. In a dry reaction flask, LDA (97 mL, 1.8 M in heptane/THF/ethylbenzene, 175 mmol) was mixed with THF (304 mL) and the solution was cooled to -78°C. 2. 2-Chloro-4-fluoropyridine (20.0 g, 152 mmol) was dissolved in 2-chloro-4-iodopyridine-3-carboxylic acid (64-2). 2. 2-chloro-4-fluoropyridine (20.0 g, 152 mmol) was dissolved in THF (50 mL) and slowly added dropwise to the cooled LDA solution described above through a constant pressure dropping funnel over 20 minutes. 3. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -78°C for 1 hour. 4. the reaction mixture was slowly poured into a container with dry ice and allowed to sublimate completely. 5. Water was added to the residue and the pH was adjusted to alkaline with 1N NaOH solution. 6. Extract the mixture with ether (Et2O) and discard the organic layer. 7. The aqueous layer was acidified to pH < 7 with 1N HCl solution and extracted with ethyl acetate (EtOAc). 8. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to give the orange solid product 64-2 (19 g, 71.2% yield). MS (ESI): m/z = 176.0 ([M+H]+).

References

[1] Patent: WO2011/53574, 2011, A1. Location in patent: Page/Page column 44

2-CHLORO-4-FLUORONICOTINIC ACID(929022-76-4)Related Product Information

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