4-Iodo-1-methyl-1H-imidazole Chemical Properties

Melting point:

51-54°C

Boiling point:

299.0±13.0 °C(Predicted)

Density 

2.07±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Dichlomethane (Slightly), Methanol (Slightly)

form 

Solid

pka

4.46±0.61(Predicted)

color 

Pale Beige

InChI

InChI=1S/C4H5IN2/c1-7-2-4(5)6-3-7/h2-3H,1H3

InChIKey

HUQSHNLGOKQVHA-UHFFFAOYSA-N

SMILES

C1N(C)C=C(I)N=1

CAS DataBase Reference

71759-87-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2933299090

4-Iodo-1-methyl-1H-imidazole Usage And Synthesis

Uses

4-Iodo-1-methylimidazole is a chemical reagent used in the synthesis of PET (positron emission tomography) tracers for imaging brain enzymes.

Synthesis

General procedure for the synthesis of 4-iodo-1-methyl-1H-imidazole from 4,5-diiodo-1-methyl-1H-imidazole: At room temperature, EtMgBr (3.0 M ether solution, 11.00 mL, 32.9 mmol) was slowly added dropwise to 4,5-diiodo-1-methyl-1H-imidazole (10.00 g, 29.9 mmol) in anhydrous CH2Cl2 ( 150 mL) solution for more than 15 minutes dropwise. The reaction mixture was then stirred for 20 minutes. After confirming complete consumption of the feedstock by TLC monitoring, the reaction was quenched by adding water (20 mL) to the reaction mixture. The organic and aqueous layers were separated and the aqueous layer was extracted with CH2Cl2 (3 x 50 mL). All organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to afford 4-iodo-1-methylimidazole (15) as a light brown oil (5.86 g, 94% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1608 - 1621
[2] Journal of Organometallic Chemistry, 2012, vol. 697, # 1, p. 33 - 40
[3] Heterocycles, 2003, vol. 60, # 1, p. 1 - 7
[4] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665
[5] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3741 - 3749

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