190903-71-0 | 2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid

CAS:190903-71-0 | 2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid,Description

2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid is a useful difluoromethylated building block for the synthesis of various benzodioxole-containing pharmaceutical active compounds. It has the molecular formula C7H5BF2O4.

Synthesis Analysis

The synthesis of 2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid involves the use of raw materials like 5-Bromo-2,2-difluorobenzodioxole and Triisopropyl borate.

Molecular Structure Analysis

The molecular structure of 2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid can be represented by the SMILES string OB(O)c1ccc2OC(F)(F)Oc2c1.

Scientific Research Applications

While specific applications of “2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid” are not readily available, boronic acids, including this compound, are often used in Suzuki–Miyaura coupling reactions . This is a type of cross-coupling reaction used to form carbon-carbon bonds, which is a key process in organic synthesis.

In these reactions, boronic acids are used as nucleophilic organic groups. They are transferred from boron to a palladium catalyst, which has undergone oxidative addition with an electrophilic organic group. This process allows for the formation of a new carbon-carbon bond.

It’s also worth noting that certain boronic acids, when in the solid state, have been found to be more resistant to protodeboronation, especially for 2-heteroaryl substrates. This could potentially make “2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid” a useful reagent in Suzuki–Miyaura couplings and other reactions where protodeboronation can be a problem.

In addition, certain boronic acids, when in the solid state, have been found to be more resistant to protodeboronation, especially for 2-heteroaryl substrates. This could potentially make “2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid” a useful reagent in Suzuki–Miyaura couplings and other reactions where protodeboronation can be a problem.

Safety And Hazards

2,2-Difluoro-benzo[1,3]dioxole-5-boronic acid is classified as an eye irritant (Eye Irrit. 2) according to the Globally Harmonized System of Classification and Labelling of Chemicals (GHS). The safety precautions include wearing protective gloves, clothing, and eye/face protection. In case of contact with eyes, rinse cautiously with water for several minutes.

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