Production Method 1

1076-43-3

25015-63-8

245043-33-8

82954-89-0

Reaction Conditions

1.1 Catalysts: Stereoisomer of bis[2,6-bis[[bis(1-methylethyl)phosphino-κP]oxy]-3,5-bis(1,1-dim… ;  14 h, 80 °C

Reference

High-Turnover Aromatic C-H Borylation Catalyzed by POCOP-Type Pincer Complexes of Iridium

Press, Loren P.; et al, Journal of the American Chemical Society, 2016, 138(30), 9487-9497

4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane Raw materials

• Benzene-d6, 99.5%
• Pinacolborane

4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane Preparation Products

• 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane (245043-33-8)
• 2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (82954-89-0)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives

Comprehensive Analysis of 4,4,5,5-Tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane (CAS No. 245043-33-8)

4,4,5,5-Tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane (CAS No. 245043-33-8) is a deuterated boronic ester compound widely used in organic synthesis, pharmaceutical research, and material science. Its unique structure, featuring a pentadeuteriophenyl group and a dioxaborolane ring, makes it a valuable tool for isotopic labeling and Suzuki-Miyaura cross-coupling reactions. This article explores its properties, applications, and relevance in modern scientific research.

The growing demand for deuterated compounds in drug development has placed 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane at the forefront of innovation. Researchers are increasingly leveraging its stability and isotopic purity to study metabolic pathways, improve NMR spectroscopy, and enhance the pharmacokinetic profiles of therapeutic agents. Its CAS No. 245043-33-8 is frequently cited in patents and academic papers, reflecting its importance in cutting-edge chemistry.

One of the most searched questions about this compound is: "How does deuterium labeling affect reaction kinetics?" Studies show that the pentadeuteriophenyl moiety in 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane can significantly alter reaction rates due to the kinetic isotope effect (KIE). This property is exploited in mechanistic studies and the design of deuterated drugs, a trending topic in medicinal chemistry.

Another hot topic is the role of boronic esters in sustainable chemistry. The dioxaborolane ring in this compound enables efficient cross-coupling reactions with minimal waste, aligning with green chemistry principles. Researchers are exploring its use in catalytic systems and polymer synthesis, addressing the demand for eco-friendly industrial processes.

From a technical perspective, the synthesis of CAS No. 245043-33-8 involves precise deuterium incorporation techniques, often using palladium-catalyzed pathways. Its high isotopic purity (>98% D) ensures reliability in applications such as mass spectrometry and isotopic tracing. The compound’s stability under ambient conditions further enhances its practicality in laboratory settings.

In the pharmaceutical industry, 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane is pivotal for developing deuterated analogs of existing drugs. This approach, known as "deuterium switching," can improve drug half-life and reduce side effects. Recent FDA approvals of deuterated drugs have spurred interest in this field, making CAS No. 245043-33-8 a key building block for next-generation therapeutics.

For researchers seeking alternatives to traditional reagents, this compound offers advantages such as compatibility with air-sensitive reactions and functional group tolerance. Its tetramethyl-substituted dioxaborolane core provides steric protection, minimizing unwanted side reactions. These attributes are frequently highlighted in forums discussing "optimizing boron-based reagents for complex syntheses."

Looking ahead, advancements in deuteration techniques and boron chemistry are expected to expand the applications of 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentadeuteriophenyl)-1,3,2-dioxaborolane. Its integration into automated synthesis platforms and high-throughput screening aligns with the industry’s shift toward precision and efficiency. As the scientific community continues to explore its potential, CAS No. 245043-33-8 remains a cornerstone of innovative research.

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