Production Method 1

943830-24-8

943831-11-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ;  rt → -60 °C; < -55 °C; 0.5 h, < -55 °C
1.2 Reagents: Trimethyl borate ;  < -55 °C; < -55 °C → rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0.5 h, rt

Reference

Preparation of 4-aminopicolic acid derivative herbicides

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(2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid Raw materials

• 1-Bromo-2-chloro-4-fluoro-3-methoxybenzene

(2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid Preparation Products

• (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid (943831-11-6)

• 1. Acenaphthenic hopanoids, a novel series of aromatised
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• 2. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
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• 3. An atom-economical protocol for direct conversion of Baylis–Hillman alcohols to β-chloro aldehydes in water?
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• 4. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
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• 5. An intermolecular C–C coupling reaction of iridium complexes?
  Kathrin Kutlescha,Rhett Kempe New J. Chem., 2010,34, 1954-1960

• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid (CAS No. 943831-11-6)

(2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid (CAS No. 943831-11-6) is a versatile and important compound in the field of organic synthesis and medicinal chemistry. This boronic acid derivative is characterized by its unique functional groups, including a chloro, fluoro, and methoxy substituent on the phenyl ring, which confer it with distinct chemical properties and reactivity. The compound has gained significant attention in recent years due to its potential applications in various synthetic transformations and its role in the development of novel pharmaceuticals.

The structure of (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid is particularly noteworthy for its ability to participate in Suzuki-Miyaura cross-coupling reactions, a widely used method for the formation of carbon-carbon bonds. This reaction is crucial in the synthesis of complex organic molecules, including those with biological activity. The presence of the boronic acid group allows for efficient coupling with aryl halides or vinyl halides, making it an essential building block in the synthesis of a wide range of compounds.

Recent research has highlighted the importance of (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid in the development of new drugs. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that this compound can be used as a key intermediate in the synthesis of novel antiviral agents. The unique combination of substituents on the phenyl ring provides a platform for fine-tuning the pharmacological properties of these agents, such as their potency and selectivity.

In addition to its use in drug discovery, (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid has also found applications in materials science. Its ability to undergo controlled polymerization reactions makes it a valuable monomer for the synthesis of functional polymers with tailored properties. These polymers have potential applications in areas such as drug delivery systems, sensors, and coatings.

The synthesis of (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid can be achieved through several methods, each with its own advantages and limitations. One common approach involves the boronation of 2-chloro-4-fluoro-3-methoxybenzene using borane reagents. This method typically yields high purity products and is scalable for industrial production. Another method involves the palladium-catalyzed borylation of 2-chloro-4-fluoro-3-methoxybenzene with boronic esters, which provides an alternative route with good functional group tolerance.

The physical and chemical properties of (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid have been extensively studied. It is a white solid that is soluble in polar solvents such as water and methanol. The compound exhibits good thermal stability and can be stored under standard laboratory conditions without significant degradation. Its reactivity is primarily driven by the boronic acid group, which can undergo various transformations under mild conditions.

In terms of safety and handling, (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid should be handled with care to avoid exposure to air and moisture, as these can lead to hydrolysis and loss of reactivity. Proper personal protective equipment (PPE) should be used when handling this compound to ensure safety.

The environmental impact of (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid has also been considered in recent studies. While it is generally considered safe for use in laboratory settings, proper disposal methods should be followed to minimize any potential environmental impact. Research into greener synthetic methods for producing this compound is ongoing, with a focus on reducing waste and improving sustainability.

In conclusion, (2-Chloro-4-fluoro-3-methoxyphenyl)boronic acid (CAS No. 943831-11-6) is a highly valuable compound with a wide range of applications in organic synthesis, medicinal chemistry, and materials science. Its unique structure and reactivity make it an essential building block for the development of new drugs and functional materials. Ongoing research continues to uncover new uses and improvements in its synthesis, further solidifying its importance in modern chemistry.

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