3-Iodo-2-methoxypyridine Chemical Properties

Melting point:

66 °C(Solv: hexane (110-54-3))

Boiling point:

131-133 °C (43 mmHg)

Density 

1.831 g/mL at 25 °C

refractive index 

1.617-1.619

Flash point:

>110℃

storage temp. 

2-8°C

pka

1.38±0.10(Predicted)

form 

clear liquid

color 

Light yellow to Brown

Sensitive 

Light Sensitive

InChI

InChI=1S/C6H6INO/c1-9-6-5(7)3-2-4-8-6/h2-4H,1H3

InChIKey

BXCHJERCAUZLOE-UHFFFAOYSA-N

SMILES

C1(OC)=NC=CC=C1I

CAS DataBase Reference

112197-15-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22-41-37/38-22-36/37/39

Safety Statements 

36/37/39-26-37

RIDADR 

UN 3334

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Iodo-2-methoxypyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Synthesis

The general procedure for the synthesis of 3-iodo-2-methoxypyridine using 2-methoxypyridine as starting material was as follows: firstly, [Li(TMP)Zn(tBu)2] was prepared in 0.4 mmol scale THF solution according to the literature method. To this solution, 2-methoxypyridine (0.042 mL, 0.4 mmol) was added and the reaction mixture was stirred at room temperature for 2 h to obtain a light orange solution. Subsequently, the solution was cooled to 0°C and the reaction was quenched with I2 (508 mg, dissolved in 1 mL THF) and stirring was continued for 1 hour. Upon completion of the reaction, 10% Na2S2O3 solution was added until the solution was bleached and the product was extracted with DCM (3 x 1 mL). The organic phases were combined, dried with MgSO4 and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using heptane:DCM (20:80→40:60) as eluent to afford 3-iodo-2-methoxypyridine (2a) as a colorless oil (87.1 mg, 92% yield).1H NMR (400 MHz, CDCl3) δ ppm 4.00 (s, 3H), 6.65 (dd, J = 7.61, 4.88 Hz, 1H), 8.03 (dd, J = 7.61, 1.76 Hz, 1H), 8.13 (dd, J = 4.88, 1.76 Hz, 1H). The data obtained are in agreement with literature reports.

References

[1] Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205
[2] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[3] Journal of the American Chemical Society, 2004, vol. 126, # 34, p. 10526 - 10527
[4] Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1921 - 1930
[5] Chemical Communications, 2014, vol. 50, # 85, p. 12859 - 12862

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