888318-22-7 | 1-bromo-3,4-difluoro-2-methoxybenzene

CAS:888318-22-7 | 1-bromo-3,4-difluoro-2-methoxybenzene,Description

1-Bromo-3,4-difluoro-2-methoxybenzene is a chemical compound with the molecular formula C7H5BrF2O. It is a solid at room temperature.

Molecular Structure Analysis

The molecular structure of 1-Bromo-3,4-difluoro-2-methoxybenzene consists of a benzene ring substituted with bromo, difluoro, and methoxy groups. The InChI code for this compound is 1S/C7H5BrF2O/c1-11-7-4(8)2-3-5(9)6(7)10/h2-3H,1H3.

Physical And Chemical Properties Analysis

1-Bromo-3,4-difluoro-2-methoxybenzene has a molecular weight of 223.02. It is a solid at room temperature. The density is approximately 1.6±0.1 g/cm3. The boiling point is around 195.7±35.0 °C.

Scientific Research Applications

Arylation in Fragrance Synthesis

1-Bromo-3,4-difluoro-2-methoxybenzene is involved in arylation processes, specifically in fragrance synthesis. The use of Pd(OAc)2 in combination with P(t-Bu)3 catalyzes the coupling of β-methallyl alcohol with bromobenzenes, including 1-bromo-4-methoxybenzene, to produce floral fragrances. This method showcases high reaction rates and chemoselectivity, making it practically feasible for industrial applications (Scrivanti, Bertoldini, Beghetto, & Matteoli, 2008) .

Synthesis of Chiral Liquid Crystals

The compound finds application in the synthesis of chiral liquid crystals. It's used in reactions with Grignard reagents, which leads to β-C-aryl glycosides. These glycosides are then used as chiral precursor compounds in the synthesis of liquid crystals. The nature of the substituent on the phenyl ring in the molecule significantly influences the mesogenic properties of these compounds (Bertini, Perrin, Sinou, Thozet, & Vill, 2003).

Synthesis of Low-Coordinate Phosphorus Compounds

In the field of chemical synthesis, 1-Bromo-3,4-difluoro-2-methoxybenzene is used in the preparation of sterically protected diphosphene and fluorenylidenephosphine. These compounds contain low-coordinate phosphorus atoms and are influenced by electronic perturbation due to the presence of a p-methoxy group. This area of research contributes to the understanding of phosphorus chemistry and its potential applications (Toyota, Kawasaki, Nakamura, & Yoshifuji, 2003).

Role in Electrochemical Processes

The compound is also significant in electrochemical processes. For instance, it's involved in the controlled-potential reduction of certain bromoethers, catalyzed by nickel(I) tetramethylcyclam. This process leads to the synthesis of tetrahydrofuran derivatives, which have various applications in chemical synthesis (Esteves, Ferreira, & Medeiros, 2007).

Catalysis in Ring Opening Reactions

1-Bromo-3,4-difluoro-2-methoxybenzene is used as a catalyst in the ring-opening of epoxides. This process affords vicinal iodo alcohols and bromo alcohols in high yields, occurring regioselectively under neutral and mild conditions. This catalytic method is particularly useful when sensitive functional groups are present (Niknam & Nasehi, 2002).

Safety And Hazards

This compound is labeled with the signal word “Warning” and has hazard statements H302, H315, H319, and H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray and washing thoroughly after handling.

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