1,3-DIBROMO-5-IODOBENZENE Chemical Properties

Melting point:

124.4-124.7℃

Boiling point:

302.7±32.0 °C(Predicted)

Density 

2.514±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

Light yellow to Brown

InChI

InChI=1S/C6H3Br2I/c7-4-1-5(8)3-6(9)2-4/h1-3H

InChIKey

KARUMYWDGQTPFL-UHFFFAOYSA-N

SMILES

C1(Br)=CC(I)=CC(Br)=C1

Safety Information

HS Code 

2903998090

1,3-DIBROMO-5-IODOBENZENE Usage And Synthesis

Uses

1,3-Dibromo-5-iodobenzene is an important organic intermediate widely used in the fields of dyes, pigments, pharmaceuticals and pesticides.

Chemical Properties

Reddish brown powder

Synthesis

The general procedure for the synthesis of 1,3-dibromo-5-iodobenzene from 2,6-dibromo-4-iodoaniline is as follows: 1. Preparation of 3,5-dibromoiodobenzene: 188.4 g of 2,6-dibromo-4-iodoaniline and 600 g of hypophosphorous acid were added to the reaction vessel at room temperature and stirred well. Subsequently, a solution formed by dissolving 34.5 g of sodium nitrite in 60 ml of water was added dropwise. The reaction is violently exothermic and the reaction temperature needs to be controlled at 20-25°C by means of a water bath. After the dropwise addition was completed, the reaction was continued for about 3 hours until a large white solid precipitate was observed. The reaction was continued at this temperature for 1 hour. The progress of the reaction was monitored by HPLC and stopped when the raw material 2,6-dibromo-4-iodoaniline completely disappeared. The crude product was collected by filtration. 2. Purification of the crude product: the crude product was dispersed in three 1000 ml flasks, 700 ml of anhydrous ethanol was added to each flask, and the product was heated to reflux (ca. 80 °C) to completely dissolve the product. Subsequently, it was cooled to 20-25 °C, the crystals were collected by filtration and dried under reduced pressure at 60 °C to obtain white needle-like crystals of 136 g. The purity of the product, 3,5-dibromo-2-iodobenzene, was 99.72% by HPLC analysis and the reaction yield was 75.2%.

References

[1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
[3] Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8661 - 8666
[4] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 882 - 896
[5] Patent: CN105523884, 2016, A. Location in patent: Paragraph 0014; 0016; 0017

1,3-DIBROMO-5-IODOBENZENE(19752-57-9)Related Product Information

• 3-BROMO-4-FLUOROANISOLE
• 1,3-Dibromo-2,5-difluorobenzene
• 2,6-Dichloro-4-fluoroiodobenzene
• 2-Bromo-5-chloro-1,3-difluorobenzene
• 1,3-DICHLORO-2,5-DIFLUOROBENZENE
• Benzene, 2-chloro-1,3-difluoro-5-iodo-
• 1-Bromo-5-chloro-2,3-difluorobenzene
• 1-Bromo-2,3-dichloro-5-fluorobenzene
• 1,3-dibroMo-2-iodobenzene
• 3,4-DIBROMOANILINE
• 3,5-Dibromoaniline
• 2,4-Dibromoaniline
• 1,3-DIBROMO-4-IODOBENZENE
• 1,2-DIBROMO-4-IODOBENZENE
• 2,6-Dibromoaniline
• 2,5-Dibromobenzenamine
• 1,4-DIBROMO-2-IODOBENZENE
• 1,3-DIBROMO-5-IODOBENZENE