4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]thiomorpholine 1,1-dioxide
[CAS# 1092563-25-1]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: 4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]thiomorpholine 1,1-dioxide
• Molecular Formula: C₁₇H₂₆BNO₄S
• Molecular Weight: 351.27
• CAS Registry Number: 1092563-25-1
• EC Number: 892-588-8
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)CN3CCS(=O)(=O)CC3

Properties

• Density: 1.19±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.549, Calc.^*
• Boiling Point: 509.0±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 261.7±30.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]thiomorpholine 1,1-dioxide is a chemical compound primarily recognized for its role in organic synthesis, particularly in the field of Suzuki-Miyaura cross-coupling reactions. This compound features a boronic ester group, known for its reactivity in palladium-catalyzed cross-coupling, enabling the formation of carbon-carbon bonds, which are crucial for constructing complex organic molecules. The discovery and utilization of boronic acid derivatives such as this one have significantly advanced organic chemistry, particularly in the development of pharmaceuticals and materials science.

This compound’s core structure includes a tetramethyl dioxaborolane moiety attached to a benzyl group, which itself is linked to a thiomorpholine 1,1-dioxide ring. The boronic ester group is essential for its reactivity in cross-coupling reactions, while the thiomorpholine sulfone structure adds a level of chemical diversity, making the compound useful in the synthesis of sulfur-containing molecules or those requiring specific electronic and steric properties.

In organic synthesis, 4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]thiomorpholine 1,1-dioxide is typically used as a boron-containing reagent in Suzuki-Miyaura reactions. This reaction is a powerful tool for forming carbon-carbon bonds, and it is widely used in pharmaceutical chemistry to create complex molecules with medicinal properties. For example, it can be employed in the synthesis of drug candidates by coupling aryl halides with boronic esters to create biaryl structures, which are common motifs in many biologically active compounds. The tetramethyl dioxaborolane group offers stability and ease of handling, which is advantageous for these applications.

Additionally, this compound is valuable in material science, where Suzuki-Miyaura coupling reactions are used to create polymers and other advanced materials. The ability to form strong carbon-carbon bonds between different organic building blocks allows for the precise design and synthesis of materials with desirable mechanical, thermal, or electronic properties. This makes boronic ester derivatives like this compound an essential part of modern polymer and material synthesis.

The thiomorpholine 1,1-dioxide portion of the molecule introduces potential utility in medicinal chemistry due to the presence of sulfur and oxygen, which can modulate the compound’s interaction with biological systems. Such structural features are often explored for their potential bioactivity, making compounds like this one of interest in drug discovery efforts aimed at targeting specific enzymes or receptors.

In summary, 4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]thiomorpholine 1,1-dioxide serves as a versatile intermediate in organic synthesis, enabling the formation of important carbon-carbon bonds through Suzuki-Miyaura cross-coupling. Its applications span pharmaceutical development, material science, and the broader field of organic chemistry, where the synthesis of complex, functional molecules is essential.

References

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