2-Chloro-6-methoxypyridine Chemical Properties

Boiling point:

185-186 °C (lit.)

Density 

1.207 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.528(lit.)

Flash point:

169 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

0.40±0.10(Predicted)

color 

Colorless to Almost colorless

BRN 

1364500

InChI

InChI=1S/C6H6ClNO/c1-9-6-4-2-3-5(7)8-6/h2-4H,1H3

InChIKey

VAVGOGHLNAJECD-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(OC)=CC=C1

CAS DataBase Reference

17228-64-7(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 2-chloro-6-methoxy-(17228-64-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

RIDADR 

2810

WGK Germany 

3

Hazard Note 

Irritant

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:2-Chloro-6-methoxypyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-6-methoxypyridine Usage And Synthesis

Chemical Properties

Clear colorless to light yellow liquid

Uses

2-Chloro-6-methoxy-pyridine is a reagent used to synthesize imidazo[1,2-a]pyrimidines as functionally selective GABAA ligands. It can also be used to synthesize oxazolidinedione-arylpyridinones as EP3 receptor antagonists.

General Description

The FT-Raman and Fourier transform infrared (FTIR) spectra of 2-Chloro-6-methoxypyridine has been studied.

Synthesis

To a stirred solution of 2,6-dichloropyridine (68.9 g, 466 mmol) in methanol (500 mL) was slowly added sodium methanolate (100 g, 1.86 mol) at room temperature. The reaction mixture was stirred continuously at 60°C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, the reaction was quenched with 2 M aqueous hydrochloric acid and extracted with dichloromethane (CH2Cl2). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford 2-chloro-6-methoxypyridine (66.9 g, quantitative yield) as a colorless oil. The product characterization data were as follows: IR (thin film method, cm?1 ): 1599, 1585, 1560, 1468, 1410, 1302, 1265, 1152, 1024, 876, 789; 1H-NMR (CDCl3, 500 MHz) δ: 7.51 (t, J = 7.37 Hz, 1H), 6.90 (d, J = 7.37 Hz, 1H), 6.65 (d, J = 7.37 Hz, 1H), 3.94 (s, 3H); 13C-NMR (CDCl3, 125 MHz) δ: 163.9, 148.4, 140.5, 116.2, 109.1, 54.0; HR-MS (ESI-TOF): the calculated C6H7ClNO [(M + H)+] value was 144.0211 and the measured value was 144.0211.

References

[1] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732
[2] Patent: CN107935922, 2018, A. Location in patent: Paragraph 0036-0038; 0039-0040; 0045-0048; 0059-0061
[3] Patent: CN106905229, 2017, A. Location in patent: Paragraph 0022; 0023
[4] Chemical & Pharmaceutical Bulletin, 1986, vol. 34, # 9, p. 3658 - 3671
[5] Patent: CN107954928, 2018, A. Location in patent: Paragraph 0017; 0018; 0019; 0020; 0021

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