5-Bromo-2,2-difluorobenzodioxole Chemical Properties

Boiling point:

78-79°C 20mm

Density 

1,74 g/cm³

refractive index 

1.4967

Flash point:

>75°C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Miscible with hexane.

form 

clear liquid

color 

Colorless to Almost colorless

BRN 

1425209

InChI

InChI=1S/C7H3BrF2O2/c8-4-1-2-5-6(3-4)12-7(9,10)11-5/h1-3H

InChIKey

SZRHWHHXVXSGMT-UHFFFAOYSA-N

SMILES

O1C2=CC=C(Br)C=C2OC1(F)F

CAS DataBase Reference

33070-32-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-41

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

2934999090

MSDS

• Language:English Provider:ALFA

5-Bromo-2,2-difluorobenzodioxole Usage And Synthesis

Uses

5-Bromo-2,2-difluoro-1,3- benzodioxole is used as a precursor in organic synthesis. It is used to prepare 5-bromo-2,2-difluoro-1,3-benzodioxole-4-carboxylic acid. It serves as an intermediate in active pharmaceutical ingredients, agrochemicals and in dyestuff field.

Synthesis

General procedure for the synthesis of 2,2-difluoro-5-bromo-1,3-benzodioxole from 2,2-difluoro-1,3-benzodioxole: In a 1000 mL round-bottomed flask fitted with a mechanical stirrer, a reflux condenser, and a pressure-equilibrium charging funnel, 2,2-difluoro-1,3-benzodioxole (200 g, 1.27 mol) and water (456 g, 25.3 mol). Bromine (284 g, 1.77 mol) was added dropwise at 25 °C for 1 hour. The temperature of the reaction mixture was increased from 25 °C to 85 °C during the dropwise addition. The reaction mixture was kept at 85 °C for 8 h. The reaction process was monitored by liquid chromatography. After completion of the reaction, the reaction mixture was cooled to 25°C. The organic and aqueous layers were separated, and the organic layer was washed sequentially with sodium bisulfite solution and sodium bicarbonate solution to obtain the crude product of 2,2-difluoro-5-bromo-1,3-benzodioxole. The crude product was purified by vacuum distillation. Yield: 80%; purity: 99.8% (determined by liquid chromatography).

References

[1] Patent: WO2017/46816, 2017, A2. Location in patent: Page/Page column 9-10
[2] Patent: EP1595877, 2005, A1. Location in patent: Page/Page column 4
[3] European Journal of Organic Chemistry, 2004, # 1, p. 64 - 68
[4] Patent: WO2016/38627, 2016, A1. Location in patent: Page/Page column 4

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