2-Chloro-3-methoxypyrazine

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2-Chloro-3-methoxypyrazine Basic information
Product Name:2-Chloro-3-methoxypyrazine
Synonyms:2-Chloro-3-methoxy-1,4-diazine;2-Chloro-3-Methoxy-pyrazin;2-CHLORO-3-METHOXY PYRAZINE,98+%;2-BROMOTHIAZOL-4-A...;Pyrazine, 2-chloro-3-methoxy-;2-Chloro-3-methoxypyrazine
CAS:40155-28-0
MF:C5H5ClN2O
MW:144.56
EINECS:
Product Categories:alkyl chloride
Mol File:40155-28-0.mol
2-Chloro-3-methoxypyrazine Structure
2-Chloro-3-methoxypyrazine Chemical Properties
Melting point 31-32 °C
Boiling point 180.3±35.0 °C(Predicted)
density 1.292±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-1.48±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
Hazard Codes Xn
Risk Statements 22
HS Code 2933998090
MSDS Information
2-Chloro-3-methoxypyrazine Usage And Synthesis
Synthesis
3-Methoxypyrazine 1-oxide

23902-69-4

2-CHLORO-6-METHOXYPYRAZINE

33332-30-8

2-CHLORO-3-METHOXYPYRAZINE

40155-28-0

General procedure for the synthesis of 2-chloro-6-methoxypiperazine and 2-chloro-3-methoxypyrazine from 2-methoxypyrazine-4-oxide (CAS: 23902-69-4): 0.98 g (0.0078 mol) of 2-methoxypyrazine-4-oxide (Example P6) was mixed with 4 mL of phosphoryl chloride and heated to reflux and stirred for 2 hours. Prior to the start of the reaction, 1.25 mL (0.0078 mol) of N,N-diethylaniline was slowly added via syringe. After completion of the reaction, the solution was cooled to 20 °C and slowly poured into ice water. After adjusting the pH of the mixture to 9 with 30% aqueous sodium hydroxide, it was extracted four times with 10 mL of chloroform. The organic phases were combined, washed sequentially with 3N hydrochloric acid and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Separation by silica gel column chromatography (eluent: ethyl acetate/isohexane, 1:8) afforded the target product 2-chloro-3-methoxypyrazine and its isomer 2-chloro-6-methoxypyrazine. 2-chloro-3-methoxypyrazine was obtained in a yield of 0.29 g (25% of the theoretical value) with 1H NMR (300 MHz, CDCl3) δ: 8.143 ppm (s, 1H), 8.131 ppm (s, 1H), 3.988 ppm (s, 3H). The yield of the isomer 2-chloro-6-methoxypyrazine was 0.38 g (33% of the theoretical value), 1H NMR (300 MHz, CDCl3) δ: 8.031 ppm (d, J = 2.7 Hz, 1H), 7.937 ppm (d, J = 2.7 Hz, 1H), 4.057 ppm (s, 3H).

References[1] Patent: WO2003/87067, 2003, A1. Location in patent: Page/Page column 39
2-Chloro-3-methoxypyrazine Preparation Products And Raw materials
Raw materials3-Methoxypyrazine 1-oxide
Preparation Products5-Methoxy-2-chloropyrazine-->2-Chloro-6-methoxypyrazine-->2-Methoxypyrazine
Tag:2-Chloro-3-methoxypyrazine(40155-28-0) Related Product Information
Methyl 3-amino-6-chloro-5-methoxypyrazine-2-carboxylate 2-Chloro-3-methoxypyrazine 2-Chloro-3-methoxyquinoxaline 5-Chloro-3-methoxypyrazine-2-carbaldehyde 3-Chloro-5-methoxypyrazine-2-carbaldehyde Methyl 6-chloro-3-methoxypyrazine-2-carboxylate 2-Chloro-6-methoxypyrazine Pyrazine 2-Chloro-5-methoxypyrazine 3-Chloro-5-(dichloromethyl)-2-methoxy-pyrazine