Production Method 1

25015-63-8

909391-56-6

878197-87-6

Reaction Conditions

1.1 Catalysts: (OC-6-21)-Bis[1,1′-(1,2-ethanediyl)bis[1,1-dimethylphosphine-κP]]dimethyliron ;  72 h, rt

Reference

Iron-Catalyzed C-H Borylation of Arenes

Dombray, Thomas; Werncke, C. Gunnar; Jiang, Shi; Grellier, Mary; Vendier, Laure; et al, Journal of the American Chemical Society, 2015, 137(12), 4062-4065

N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine Raw materials

• Pinacolborane

N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine Preparation Products

• N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (909391-56-6)
• N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (878197-87-6)

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

N,N-Dimethyl-1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (CAS No. 909391-56-6): A Comprehensive Overview

N,N-Dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (CAS No. 909391-56-6) is a versatile organic compound that has gained significant attention in the fields of medicinal chemistry and materials science. This compound, commonly referred to as DMABPin, is a boronic ester derivative that plays a crucial role in various synthetic transformations and biological applications. Its unique chemical structure and reactivity make it an essential building block in the development of novel pharmaceuticals and advanced materials.

The chemical structure of N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine consists of a phenyl ring substituted with a boronic ester group and a dimethylamino group. The boronic ester functionality is particularly noteworthy due to its ability to undergo Suzuki-Miyaura coupling reactions, which are widely used in the synthesis of complex organic molecules. This reaction allows for the efficient formation of carbon-carbon bonds between aryl or vinyl halides and boronic acids or esters, making DMABPin an invaluable reagent in organic synthesis.

In the context of medicinal chemistry, N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine has been explored for its potential therapeutic applications. Recent studies have shown that compounds containing boronic ester groups can exhibit anti-inflammatory and anti-cancer properties. For instance, a study published in the Journal of Medicinal Chemistry reported that DMABPin derivatives demonstrated significant inhibition of cancer cell proliferation by targeting specific signaling pathways involved in cell growth and survival.

The dimethylamino group in N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine also contributes to its biological activity. Amino groups are known to enhance the solubility and bioavailability of organic compounds, making them more suitable for pharmaceutical applications. Additionally, the presence of this functional group can influence the binding affinity and selectivity of the compound towards specific biological targets.

From a materials science perspective, N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine has been utilized in the development of functional polymers and coatings. The boronic ester functionality can be incorporated into polymer chains to create materials with tunable properties such as pH responsiveness and self-healing capabilities. These materials have potential applications in areas such as drug delivery systems and smart coatings for various industrial and biomedical uses.

The synthesis of N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine typically involves several steps. One common approach is to start with 3-bromobenzaldehyde and perform a reductive amination with dimethylamine to form the corresponding amine. Subsequently, the bromo group is converted into a boronic ester using bis(pinacolato)diboron (B₂(pin)₂) under palladium catalysis. This method provides high yields and good purity of the final product.

In terms of safety and handling, it is important to note that while N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine is not classified as a hazardous material under current regulations (such as those outlined by OSHA or GHS), proper precautions should still be taken when handling this compound. This includes wearing appropriate personal protective equipment (PPE) such as gloves and safety goggles to prevent skin contact and inhalation.

The versatility of N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine has led to its widespread use in both academic research and industrial applications. Researchers continue to explore new synthetic methods and applications for this compound to expand its utility in various fields. For example, recent advancements in organocatalysis have opened up new avenues for using DMABPin in asymmetric synthesis reactions to produce enantiomerically pure compounds.

In conclusion,N,N-dimethyl-1-[3-(4，4，5，5-tetramethyl-1，3，2-dioxaborolan - 2 - yl) phenyl] methanamine (CAS No. 909391 - 56 - 6) is a multifunctional compound with significant potential in medicinal chemistry and materials science. Its unique chemical structure and reactivity make it an essential reagent for synthetic transformations and biological applications. As research continues to advance in these areas,N,N - dimethyl - 1 - [3 - (4，4，5，5 - tetramethyl - 1，3，2 - dioxaborolan - 2 - yl) phenyl] methanamine is likely to play an increasingly important role in the development of novel drugs and advanced materials.

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