4,5-Diiodo-1H-imidazole Chemical Properties

Melting point:

197-198°C

Boiling point:

436.9±30.0 °C(Predicted)

Density 

3.042±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.31±0.10(Predicted)

form 

solid

color 

Off-white

InChI

InChI=1S/C3H2I2N2/c4-2-3(5)7-1-6-2/h1H,(H,6,7)

InChIKey

XMWPTVMTXKJONE-UHFFFAOYSA-N

SMILES

C1NC(I)=C(I)N=1

CAS DataBase Reference

15813-09-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933299090

4,5-Diiodo-1H-imidazole Usage And Synthesis

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 4,5-diiodoimidazole from imidazole was as follows: a mixture of potassium iodide (KI, 29.3 g, 176.0 mmol) and iodine (I2, 22.4 g, 88.0 mmol) in water (60 mL) was added to a solution of 1H-imidazole (3.0 g, 44.1 mmol) dissolved in 2M sodium hydroxide (NaOH, 10.6 g, 264.5 mmol) solution. The reaction mixture was stirred at 20 °C for 3 h and subsequently neutralized by adjusting the pH to 7 with 6 M hydrochloric acid (HCl). The resulting solid product was collected by filtration and purified by recrystallization with ethanol to give the final 4,5-diiodoimidazole as an anhydrous solid (14.0 g, 99.0% yield). The melting point was 166-168 °C. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 12.75 (broad peak, 1H), 7.8 (broad peak, 1H). Mass spectrum (EI) m/z: 320.8 [MH]+.

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 293 - 304
[2] Patent: CN107501272, 2017, A. Location in patent: Paragraph 0085; 0086; 0087; 0088
[3] Synlett, 2004, # 7, p. 1306 - 1308
[4] Advanced Synthesis and Catalysis, 2013, vol. 355, # 2-3, p. 499 - 507
[5] Advanced Synthesis and Catalysis, 2013, vol. 355, # 16, p. 3231 - 3243

4,5-Diiodo-1H-imidazole(15813-09-9)Related Product Information

• Levamisole hydrochloride
• Levamisole
• Mizolastine
• Mebendazole
• 1,1'-Carbonyldiimidazole
• Imidazole
• Midazolam
• 2,4,5-Triiodoimidazole
• 1-Methyl-4,5-diiodo-1h-imidazole
• N,N-Dimethyl 4,5-Diiodo-1H-imidazole-1-sulphonamide,N,N-DIMETHYL 4,5-DIIODO-1H-IMIDAZOLE-1-SULFONAMIDE
• 4,5-Diiodo-2-methyl-1H-imidazole
• 4,5-Dibromo-1H-imidazole
• 2,4-DIIODO-1H-IMIDAZOLE
• 4,5-Diiodo-1H-imidazole
• 1-[(benzyloxy)methyl]-4,5-diiodo-1H-imidazole
• 2,5-DIIODO-1H-IMIDAZOLE
• 2-CYCLOHEXYL-4,5-DIIODO-1H-IMIDAZOLE
• 1-(3-FLUOROBENZYL)-4,5-DIIODO-2-METHYL-1H-IMIDAZOLE