| Identification | More | [Name]
4,5-Diiodo-1H-imidazole | [CAS]
15813-09-9 | [Synonyms]
4,5-DIIODO-1H-IMIDAZOLE
4,5-DIIODOIMIDAZOLE | [EINECS(EC#)]
202-303-5 | [Molecular Formula]
C3H2I2N2 | [MDL Number]
MFCD00963878 | [Molecular Weight]
319.87 | [MOL File]
15813-09-9.mol |
| Chemical Properties | Back Directory | [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 | [form ]
solid | [pka]
9.31±0.10(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HazardClass ]
IRRITANT | [HS Code ]
2933299090 |
| Hazard Information | Back Directory | [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 |
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