5-Amino-2-chloro-3-picoline Chemical Properties

Melting point:

90.0 to 94.0 °C

Boiling point:

304.7±37.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystalline

pka

2.06±0.10(Predicted)

color 

White to Brown

InChI

InChI=1S/C6H7ClN2/c1-4-2-5(8)3-9-6(4)7/h2-3H,8H2,1H3

InChIKey

VSBISZPNLZFTPG-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C(C)C=C1N

CAS DataBase Reference

38186-82-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41-36/37/38-20/21/22

Safety Statements 

26-39-36/37/39

RIDADR 

2811

WGK Germany 

3

HS Code 

29333990

5-Amino-2-chloro-3-picoline Usage And Synthesis

Chemical Properties

Light yellow solid

Synthesis

The general procedure for the synthesis of 2-chloro-3-methyl-5-nitropyridine from 2-chloro-3-methyl-5-nitropyridine was as follows: over a period of 2 h, iron powder (9.75 g, 0.174 mol, Sigma-Aldrich) was added in batches to a stirred 2-chloro-3-methyl-5-nitropyridine (10 g, 0.058 mol, Combi) acetic acid/ water (29 mL:88 mL) solution. After 3 hours of reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. After separation of the organic layer, the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed sequentially with aqueous sodium bicarbonate and brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 6-chloro-5-methylpyridin-3-amine as a brown solid (8.0 g, 97% yield). Mass spectrum (MS) m/z = 142.03 [M + H]+. 1H-NMR (300 MHz, DMSO-d6) δ: 7.54 (d, J = 30 Hz, 1H), 6.91-6.90 (dd, J = 0.6 Hz and 2.7 Hz, 1H), 5.39 (s, 2H), 2.17 (s, 3H).

References

[1] Patent: WO2014/138484, 2014, A1. Location in patent: Page/Page column 156
[2] Patent: WO2016/22724, 2016, A1. Location in patent: Page/Page column 296
[3] Journal of Organic Chemistry, 2011, vol. 76, # 23, p. 9841 - 9844
[4] Synthetic Communications, 2006, vol. 36, # 9, p. 1235 - 1245
[5] Organic Letters, 2016, vol. 18, # 11, p. 2774 - 2776

5-Amino-2-chloro-3-picoline(38186-82-2)Related Product Information

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