1,3,5-Trifluoro-2,4,6-triiodobenzene Chemical Properties

Melting point:

152℃

Boiling point:

352.4±37.0 °C(Predicted)

Density 

3.029±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

Solid

Appearance

Off-white to light brown Solid

Water Solubility 

Slightly soluble in water.

Sensitive 

Light Sensitive

InChI

InChI=1S/C6F3I3/c7-1-4(10)2(8)6(12)3(9)5(1)11

InChIKey

NTAZOPPTLZSXQH-UHFFFAOYSA-N

SMILES

C1(F)=C(I)C(F)=C(I)C(F)=C1I

CAS DataBase Reference

84322-56-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2903998090

1,3,5-Trifluoro-2,4,6-triiodobenzene Usage And Synthesis

Uses

1,3,5-Trifluoro-2,4,6-triiodobenzene is useful for biological applications. Further, it is used as an intermediate in organic synthesis.

Synthesis

The general procedure for the synthesis of 1,3,5-trifluoro-2,4,6-triiodobenzene from 1,3,5-trifluorobenzene was as follows: potassium iodide (KI, 7.14 g, 43.56 mmol) was slowly added to a stirring mixture of periodate (3.30 g, 14.50 mmol) and concentrated sulfuric acid (20 mL) at 0 °C. The resulting dark-colored mixture was cooled in an ice bath while 1,3,5-trifluorobenzene (1.0 mL, 9.68 mmol) was added dropwise over 25 min. Subsequently, the reaction mixture was heated to 70 °C and maintained at this temperature for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and poured into ice water. Extraction was carried out with ether (3 x 50 mL) and the organic phases were combined. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3), aqueous sodium thiosulfate (Na2S2O3) and distilled water, and then dried with anhydrous sodium sulfate (Na2SO4). After evaporation to remove the solvent, the pure white powdery product 1,3,5-trifluoro-2,4,6-triiodobenzene was obtained in 80% yield. The product was characterized as follows: 19F NMR (CDCl3, 235MHz): δ-69.90ppm; melting point: 158-159°C; FT-IR (KBr pressed sheet, cm-1): 1561, 1401, 1325, 1048, 704, 652.

References

[1] Chemistry - A European Journal, 2018, vol. 24, # 56, p. 15003 - 15012
[2] European Journal of Organic Chemistry, 2002, # 23, p. 3927 - 3935
[3] Chemical Communications, 2008, # 14, p. 1635 - 1637
[4] Chemical Communications, 2017, vol. 53, # 69, p. 9590 - 9593
[5] Molecules, 2017, vol. 22, # 12,

1,3,5-Trifluoro-2,4,6-triiodobenzene(84322-56-5)Related Product Information

• 1-Bromo-4-iodobenzene
• 4-Iodoanisole
• Trifluoroacetic acid
• (Trifluoromethoxy)benzene
• (Diacetoxyiodo)benzene
• Benzotrifluoride
• Trifluoromethanesulfonic acid
• Trifluoroacetic anhydride
• Chromium(VI) oxide
• 2,4,6-TRIFLUOROIODOBENZENE
• 1-Fluoro-2-iodobenzene
• 2,4-Difluoroiodobenzene
• 2,6-Difluoroiodobenzene
• 1,3,5-Trifluoro-2,4,6-triiodobenzene