2357-52-0 | 4-Bromo-2-fluoroanisole

CAS:2357-52-0 | 4-Bromo-2-fluoroanisole,Description

Synthesis Analysis

The synthesis of 4-Bromo-2-fluoroanisole involves several chemical reactions, including bromination and hydrolysis processes. A practical method for its synthesis has been developed, utilizing diazotization of 2-fluoro-4-bromoaniline with sodium nitrite and an organic or inorganic acid to generate the diazonium salt for coupling with benzene, despite challenges such as the formation of dark decomposition products which lower yield and complicate product isolation (Qiu et al., 2009). Another synthesis approach involves a one-pot method, optimizing reaction conditions for improved yield (Li Yong-qiang, 2012).

Molecular Structure Analysis

The molecular structure and conformational properties of 2-fluoroanisole, a related compound, have been studied through gas electron diffraction and quantum chemical methods, revealing the existence of planar and nonplanar forms and providing insights into the stereochemical peculiarities of ortho derivatives of anisole (Novikov et al., 2003).

Chemical Reactions and Properties

The chemical reactions of 4-Bromo-2-fluoroanisole involve its utility as an intermediate in the synthesis of biologically active compounds. One notable reaction is its participation in the synthesis of 1-(4-Bromo-2-fluorophenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one, highlighting its importance in medicinal chemistry (Wang et al., 2016).

Physical Properties Analysis

Research on related compounds, such as 2-fluoroanisole, has provided insights into the conformational properties and preferred conformations, which are relevant for understanding the physical properties of 4-Bromo-2-fluoroanisole. The structural parameters and conformational compositions have been explored through studies on molecular structures and gas-phase analyses (Novikov et al., 2003).

Chemical Properties Analysis

The chemical properties of 4-Bromo-2-fluoroanisole include its reactivity and role as an intermediate in organic syntheses, particularly in the pharmaceutical industry. The compound's utility in synthesizing complex molecules with biological activity underscores its chemical versatility and significance (Qiu et al., 2009); (Wang et al., 2016).

Scientific Research Applications

Application 1: Synthesis of 1,4-bis[(3′-fluoro-4′-n alkoxyphenyl)ethynyl]benzenes

• Summary of the Application: 4-Bromo-2-fluoroanisole is used as a starting material in the synthesis of 1,4-bis[(3′-fluoro-4′-n alkoxyphenyl)ethynyl]benzenes.
• Results or Outcomes: The outcome of this synthesis is a series of compounds with varying lengths of alkoxy chains (n=1-12). These compounds could potentially be used in further research or applications.

Application 2: Synthesis of 7-fluoro-6-methoxy-1-methyl-2-naphthaldehyde

• Summary of the Application: 4-Bromo-2-fluoroanisole is used as a starting material in the synthesis of 7-fluoro-6-methoxy-1-methyl-2-naphthaldehyde.
• Results or Outcomes: The outcome of this synthesis is 7-fluoro-6-methoxy-1-methyl-2-naphthaldehyde, a compound that could potentially be used in further research or applications.

Application 3: Synthesis of 5,7-difluoro-6-methoxy-1-methyl-2-naphthaldehyde

• Summary of the Application: 4-Bromo-2-fluoroanisole is used as a starting material in the synthesis of 5,7-difluoro-6-methoxy-1-methyl-2-naphthaldehyde.
• Results or Outcomes: The outcome of this synthesis is 5,7-difluoro-6-methoxy-1-methyl-2-naphthaldehyde, a compound that could potentially be used in further research or applications.

Application 4: Synthesis of liquid crystals with terminal difluoromethoxy group and backbone of phenylbicyclohexane

• Summary of the Application: 4-Bromo-2-fluoroanisole is used as a starting material in the synthesis of liquid crystals with terminal difluoromethoxy group and backbone of phenylbicyclohexane.
• Results or Outcomes: The outcome of this synthesis is a series of liquid crystals with terminal difluoromethoxy group and backbone of phenylbicyclohexane. These compounds could potentially be used in further research or applications.

Application 5: Synthesis of (5-fluoro-2-methoxyphenyl)methanol

• Summary of the Application: 4-Bromo-2-fluoroanisole is used as a starting material in the synthesis of (5-fluoro-2-methoxyphenyl)methanol.
• Results or Outcomes: The outcome of this synthesis is (5-fluoro-2-methoxyphenyl)methanol, a compound that could potentially be used in further research or applications.

Safety And Hazards

4-Bromo-2-fluoroanisole is considered hazardous. It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray, and use only outdoors or in a well-ventilated area. Protective measures such as wearing protective gloves, clothing, and eye/face protection are advised.

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