3-CHLORO-6-METHOXYPYRIDAZINE Chemical Properties

Melting point:

84-85 °C(lit.)

Boiling point:

285℃

Density 

1.292

Flash point:

126℃

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

0.74±0.10(Predicted)

color 

White to Almost white

BRN 

118854

InChI

InChI=1S/C5H5ClN2O/c1-9-5-3-2-4(6)7-8-5/h2-3H,1H3

InChIKey

XBJLKXOOHLLTPG-UHFFFAOYSA-N

SMILES

C1(Cl)=NN=C(OC)C=C1

CAS DataBase Reference

1722-10-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-CHLORO-6-METHOXYPYRIDAZINE Usage And Synthesis

Uses

3-Chloro-6-methoxypyridazine was used in the preparation of number of α-aryl-α-(pyridazin-3-yl)-acetonitriles.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 1466, 1995 DOI: 10.1021/jo00110a059

General Description

3-Chloro-6-methoxypyridazine undergoes regioselective metallation using various lithium alkylamides, temperatures and solvents (THF and ether). It was lithiated using lithium 2,2,6,6-tetramethylpiperidide during the synthesis of minaprine.

Synthesis

A methanolic solution of 0.5 M sodium methanolate (NaOMe/MeOH, 7.4 mL, 3.69 mmol) was slowly added dropwise to a solution of anhydrous tetrahydrofuran (12 mL) containing 3,6-dichloropyridazine (500 mg, 3.36 mmol), and the reaction mixture was stirred for 1 h at room temperature. Subsequently, the reaction was quenched by the addition of water. The reaction mixture was extracted with ethyl acetate and the organic phases were combined. The organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 6-methoxy-3-chloropyridazine (436 mg, 90% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 4.12 (s, 3H), 6.98 (d, J = 9.2 Hz, 1H), 7.38 (d, J = 9.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 55.5 (d, J = 9.2 Hz, 1H). CDCl3) δ 55.2, 119.9, 130.6, 150.9, 164.2.

References

[1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 509 - 513
[2] Patent: US2010/261727, 2010, A1. Location in patent: Page/Page column 31
[3] ACS Chemical Neuroscience, 2017, vol. 8, # 11, p. 2374 - 2380
[4] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 5, p. 1165 - 1173
[5] Journal of the American Chemical Society, 1959, vol. 81, p. 6511,6512

3-CHLORO-6-METHOXYPYRIDAZINE(1722-10-7)Related Product Information

• 3-Chloro-6-methylpyridazine
• 6-chloro-N-(propan-2-yl)pyridazin-3-amine
• 3-chloro-6-(chloroMethyl)pyridazine hydrochloride
• 3-Chloro-6-trifluoromethyl-pyridazine
• 3-Chloro-6-chloromethylpyridazine
• 3-chloro-6-isopropylpyridazine
• 3-CHLORO-6-PROPYLOXYPYRIDAZINE
• 3-Chloro-6-hydrazinopyridazine
• 3-Chloro-6-(1H-pyrazol-1-yl)pyridazine
• 6-Chloro-N-ethylpyridazin-3-amine
• 3-Chloro-6-iodopyridazine
• 6-CHLOROPYRIDAZINE-3-THIOL
• 3-CHLORO-6-PHENYLPYRIDAZINE
• 3-(TERT-BUTOXY)-6-CHLOROPYRIDAZINE
• 3-CHLORO-6-PHENOXYPYRIDAZINE
• 3-CHLORO-6-ISOPROPOXYPYRIDAZINE
• 3-CHLORO-6-ETHOXYPYRIDAZINE
• 2-Chloro-10-methyl-3,4-diazaphenoxazine