Identification | More | [Name]
2,2-Difluoro-1,3-benzodioxole | [CAS]
1583-59-1 | [Synonyms]
2,2-DIFLUORO-1,3-BENZODIOXOLE 2,2-DIFLUORO-BENZO[1,3]DIOXOLE 2,2-DIFLUOROBENZODIOXOLE LABOTEST-BB LT01148491 difluoromethylenedioxybenzene 1,2-[(Difluoromethylene)dioxy]benzene 2,2-Difluoro-1,3-benzodioxole 98% 2,2-Difluoro-1,3-benzodioxole98% 2,2-Difluoro-2H-1,3-benzodioxole | [EINECS(EC#)]
216-431-4 | [Molecular Formula]
C7H4F2O2 | [MDL Number]
MFCD00236217 | [Molecular Weight]
158.1 | [MOL File]
1583-59-1.mol |
Chemical Properties | Back Directory | [Boiling point ]
129-130°C | [density ]
1,308 g/cm3 | [refractive index ]
1.443 | [Fp ]
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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN1993 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
2932990090 |
Hazard Information | Back Directory | [Chemical Properties]
Colorless to pale yellow liquid | [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. |
Questions And Answer | Back Directory | [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.
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