2,2-Difluoro-1,3-benzodioxole Chemical Properties

Boiling point:

129-130°C

Density 

1,308 g/cm³

refractive index 

1.443

Flash point:

129-130°C

storage temp. 

2-8°C

solubility 

Chloroform, Methanol

form 

Oil

color 

Clear Colourless

BRN 

1307648

InChI

InChI=1S/C7H4F2O2/c8-7(9)10-5-3-1-2-4-6(5)11-7/h1-4H

InChIKey

DGCOGZQDAXUUBY-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2OC1(F)F

LogP

2.96

CAS DataBase Reference

1583-59-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43

Safety Statements 

26-36/37/39-36/37

RIDADR 

UN1993

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

2932990090

MSDS

• Language:English Provider:ALFA

2,2-Difluoro-1,3-benzodioxole Usage And Synthesis

Uses

2,2-Difluoro-1,3-benzodioxole is an intermediate compound which is used especially for the preparation of products for agricultural chemistry and for the synthesis of pharmaceutical products.
2,2-difluoro-1,3-benzodioxole is a useful difluoromethylated building block for the synthesis of various benzodioxole-containing pharmaceutical active compounds.
2-,3-,and 4-(Trifluoromethoxy)phenyllithiums: Versatile intermediates offering access to a variety of new organofluorine compounds.
Selective aliphatic fluorination by halogen exchange in mild conditions.

Preparation

2,2-Difluoro-1,3-benzodioxole is prepared by reaction of 2,2-dichloro-1,3-benzodioxole with potassium fluoride in the presence of an effective quantity of a catalyst selected from potassium hydrogen fluoride, sodium hydrogen fluoride, cesium hydrogen fluoride, rubidium hydrogen fluoride, and quaternary ammonium hydrogen fluoride.
https://patents.google.com/patent/US5432290A/en

References

[1] E.Castagnetti, et al, Eur. J. Org. Chem., 2001, 2001(4), pp 691-695.
[2] L.Saint-Jalmes, J. F. Chem., 2006, 127(1), pp 85-90.

Chemical Properties

Colorless to pale yellow liquid

Uses

2,2-Difluoro-1,3-benzodioxole is used in the synthesis of Kv3 inhibitors as well as in the preparation of renin inhibitors.

Synthesis

The general procedure for synthesizing 2,2-difluoro-1,3-benzodioxole from piperylene ring was as follows: first, 100 g of benzodioxole and 900 g of acetonitrile were accurately weighed and mixed to prepare a solution of benzodioxole acetonitrile with a mass fraction of 10%. Subsequently, 1 g of trifluoroacetic acid was added to this solution and mixed thoroughly. Next, a fluorine gas-nitrogen mixture with a mass fraction of 10% was prepared by adjusting the flow rate of fluorine gas and nitrogen gas. The reaction process shown in FIG. 1 was employed, using a microchannel reactor made of silicon carbide. The liquid volume of each module was set to 1 ml and the reaction temperature was controlled at -20 °C. The reaction residence time was controlled by adjusting the pumping rate to 20 s. In module A, a 10% mass fraction benzodioxole acetonitrile solution containing 1% trifluoroacetic acid was continuously pumped for pre-cooling. At the same time, a 10% mass fraction fluorine gas mixture was continuously and uniformly passed into the B module, in which the molar amount of fluorine gas was 2.2 times that of benzodioxole. After the reactants were mixed and reacted in the CDEF module, they entered a gas-liquid separator for separation. The separated gas was treated and discharged, while the liquid was washed and distilled, resulting in 1,3-benzodioxole-2,2-difluorine product with 90% yield and 99% content.

References

[1] Patent: CN108383825, 2018, A. Location in patent: Paragraph 0020-0039; 0044-0047

2,2-Difluoro-1,3-benzodioxole(1583-59-1)Related Product Information

• hexafluorobenzene
• (Trifluoromethoxy)benzene
• Benzotrifluoride
• m-Phenylenediamine
• Florfenicol
• 1-Fluoro-2-nitrobenzene
• 4-Fluoroacetophenone
• Transfluthrin
• Phthalic acid
• 3-(Trifluoromethyl)benzaldehyde
• 1,3-Difluorobenzene
• Phenylmethylsulfonyl fluoride
• 1,3-Benzodioxole
• 4-Fluorobenzoyl chloride
• 2,2-DIFLUORO-1,3-BENZODIOXOLE-4-CARBOXALDEHYDE
• 5-AMINO-2,2-DIFLUORO-1,3-BENZODIOXOLE,5-Amino-2,2-difluoro-1,3-benzodioxole, 97+%
• 5-Bromo-2,2-difluorobenzodioxole
• 2,2,5-Trifluoro-1,3-benzodioxole