5-CHLORO-PYRAZINE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

150-151℃

Boiling point:

330.9±37.0 °C(Predicted)

Density 

1.579±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.68±0.10(Predicted)

color 

White to Light yellow

InChI

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

InChIKey

FXJOTWLLDJYKAG-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=C(Cl)N=C1

CAS DataBase Reference

36070-80-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2933998090

5-CHLORO-PYRAZINE-2-CARBOXYLIC ACID Usage And Synthesis

Uses

5-Chloropyrazine-2-carboxylic acid

Synthesis

Example 29: Synthesis of 5-[2(R)-(3-chloro-4-methylsulfonyl-phenyl)-3-cyclopentylpropylamino]-pyrazine-2-carboxylic acid hydroxylamides [000197] General steps: 1. dissolve methyl 5-chloropyrazine-2-carboxylate (30.00 g, 0.17 mol) in tetrahydrofuran (87 mL). 2. a solution of potassium carbonate (72.08 g, 0.52 mol) in water (261 mL) was added to the above solution. 3. The reaction mixture was stirred at 25 °C for 42 h. 4. 4. Upon completion of the reaction, the reaction mixture was acidified to a pH of about 2 with concentrated hydrochloric acid. 5. The reaction mixture was diluted with saturated aqueous sodium chloride solution (300 mL). 6. Extracted successively with ethyl acetate (4 L total) until no product was detected in the aqueous layer. 7. The organic layers were combined, dried over sodium sulfate and filtered. 8. The filtrate was concentrated in vacuum to give 5-chloropyrazine-2-carboxylic acid (26.54 g, 96% yield) as an off-white solid. Physical properties: melting point 150-151°C; EH-HRMS m/e calculated value C5H3ClN2O2 (M+) 157.9883, measured value 157.9877.

References

[1] Patent: WO2004/52869, 2004, A1. Location in patent: Page 115 - 116
[2] Patent: WO2006/66173, 2006, A2. Location in patent: Page/Page column 71-72
[3] Patent: US2010/210621, 2010, A1
[4] Patent: US2010/210841, 2010, A1. Location in patent: Page/Page column 18
[5] Organic Process Research and Development, 2017, vol. 21, # 3, p. 346 - 356

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