3-IODO-4-METHOXY-PYRIDINE

3-IODO-4-METHOXY-PYRIDINE Property

Melting point:

78 °C(Solv: ligroine (8032-32-4))

Boiling point:

271.2±25.0 °C(Predicted)

Density 

1.825±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

4.52±0.18(Predicted)

form 

solid

Appearance

White to yellow Solid

InChI

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

InChIKey

WZAPSURIRLYQEJ-UHFFFAOYSA-N

SMILES

C1=NC=CC(OC)=C1I

Safety

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-IODO-4-METHOXY-PYRIDINE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 3-iodo-4-methoxypyridine from 4-methoxypyridine was as follows: n-butyllithium (ca. 1.6 M hexane solution, 1.5 mmol) was sequentially added to a stirred solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in tetrahydrofuran (THF, 2-3 mL) at 0 °C. After 5 min, n-butyllithium (ca. 1.6 M hexane solution, 1.5 mmol) was added. ZnCl2TMEDA complex (0.13 g, 0.50 mmol). The reaction mixture was continued to be stirred at 0 °C for 15 min and then 4-methoxypyridine (1.0 mmol) was added at 0-10 °C. After the reaction mixture was stirred for 2 h at room temperature, a THF (4 mL) solution of iodine (I2, 0.38 g, 1.5 mmol) was added. After the mixture was stirred overnight, the reaction was quenched by the addition of saturated aqueous sodium thiosulfate (Na2S2O3) solution (4 mL) and extracted with ethyl acetate (AcOEt, 320 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. Finally, the target product, 3-iodo-4-methoxypyridine, was purified by silica gel column chromatography (eluent given in the product specification).

References

[1] Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205
[2] Tetrahedron, 1993, vol. 49, # 37, p. 8373 - 8380
[3] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[4] Chemical Communications, 2014, vol. 50, # 85, p. 12859 - 12862
[5] Chemistry - A European Journal, 2013, vol. 19, # 24, p. 7944 - 7960