6-Chloro-4-pyrimidinecarboxylic acid Chemical Properties

Boiling point:

343.7±22.0 °C(Predicted)

Density 

1.579±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

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

pka

2.44±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C5H3ClN2O2/c6-4-1-3(5(9)10)7-2-8-4/h1-2H,(H,9,10)

InChIKey

RWSPRTBXAXZIOS-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC(C(O)=O)=N1

Safety Information

HS Code 

29335990

6-Chloro-4-pyrimidinecarboxylic acid Usage And Synthesis

Synthesis

General procedure for the synthesis of 6-chloropyrimidine-4-carboxylic acid from 6-hydroxy-4-pyrimidinecarboxylic acid: 2 g of 6-hydroxy-4-pyrimidinecarboxylic acid was dissolved in 30 mL of ethyl acetate, and oxalyl chloride (3.75 mL, 3 eq., 0.043 mol) was slowly added, followed by the addition of a few drops of N,N-dimethylformamide (gas was observed to escape). The reaction mixture was heated to reflux at 75 °C for 3 h, subsequently cooled to room temperature and allowed to stand overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a black solid product in quantitative yield. The resulting solid was to be stored under nitrogen protection at 4 °C.1H NMR analysis showed the product to be a mixture of 6-chloropyrimidine-4-carboxylic acid and its corresponding chloride derivatives (unstable at room temperature).1H NMR (d6-DMSO) data were as follows: 9.28 (s, 1H), 8.18 (s, 1H) for 6-chloropyrimidine-4-carboxylic acid; 8.45 (s, 1H), 8.45 (s, 1H), 8.93 (s, 1H), 8.45 (s, 1H), 8.45 (s, 1H), 8.45 (s, 1H), 6.93 (s, 1H) and 8.45 (s, 1H). 6.93 (s, 1H) for the signals of the chloride derivatives.

References

[1] Patent: WO2010/20432, 2010, A2. Location in patent: Page/Page column 91-92