1-BROMO-3-CHLORO-2-IODOBENZENE

1-BROMO-3-CHLORO-2-IODOBENZENE Property

Melting point:

75-76 °C(Solv: ethanol (64-17-5))

Boiling point:

285.9±20.0 °C(Predicted)

Density 

2.272±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

Appearance

Off-white to light brown Solid

Sensitive 

Light Sensitive

InChI

InChI=1S/C6H3BrClI/c7-4-2-1-3-5(8)6(4)9/h1-3H

InChIKey

GIMVCZMZRZGDTL-UHFFFAOYSA-N

SMILES

C1(Br)=CC=CC(Cl)=C1I

Safety

HS Code 

2903998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

1-BROMO-3-CHLORO-2-IODOBENZENE Chemical Properties,Usage,Production

Synthesis

Step 1. Synthesis of 1-bromo-3-chloro-2-iodobenzene: To an anhydrous THF (664 mL) solution containing diisopropylamine (76 mL, 0.4 mol) was slowly added dropwise a n-hexane (220 mL) solution of 2.5 M n-butyllithium (n-BuLi, 160 mL, 0.4 mol) at -78 °C for 1 h under nitrogen protection. The reaction temperature was maintained at -78 °C and stirring was continued for 1 h. A solution of 1-bromo-3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added slowly dropwise. After the dropwise addition, the reaction was kept at -78 °C for 1 h. Subsequently, a solution of anhydrous THF (400 mL) with iodine (101 g, 0.4 mol) was added slowly dropwise. The reaction system was gradually warmed to room temperature over 2 hours and stirring was continued at room temperature for 18 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to give the crude product (120 g). The crude product was purified by distillation under reduced pressure to give 1-bromo-3-chloro-2-iodobenzene (115 g, 91% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) and mass spectrometry (MS): 1H NMR δ 7.12-7.18 (t, 1H), 7.35-7.41 (dd, 1H), 7.49-7.54 (dd, 1H); MS (E/Z): 317 (M+H+).

References

[1] Patent: WO2008/124575, 2008, A1. Location in patent: Page/Page column 103
[2] Patent: US2010/317697, 2010, A1. Location in patent: Page/Page column 47
[3] Patent: WO2008/124582, 2008, A1. Location in patent: Page/Page column 86-87
[4] Patent: WO2007/117560, 2007, A2. Location in patent: Page/Page column 169
[5] Patent: WO2008/124577, 2008, A1. Location in patent: Page/Page column 69