Cas no 1256355-23-3 (3-Dimethylaminophenylboronic acid, hydrochloride)

3-Dimethylaminophenylboronic acid hydrochloride is a specific boronic acid derivative featuring a para-linked dimethylamino group substituent on the phenyl ring. Its key advantage lies in the combination of the versatile boronic acid group, which facilitates reactions like Suzuki couplings and Diels-Alder reactions, with the electron-donating dimethylamino group. The hydrochloride salt formation significantly enhances its aqueous solubility compared to the free acid, making it more suitable for handling in aqueous media or biological contexts where solubility is critical. This compound represents a valuable reagent for various synthetic transformations requiring both boron-based functionality and improved water-soluble characteristics.
3-Dimethylaminophenylboronic acid, hydrochloride structure
1256355-23-3 structure
Product Name:3-Dimethylaminophenylboronic acid, hydrochloride
CAS No:1256355-23-3
MF:C8H13BClNO2
MW:201.458321332932
MDL:MFCD04112542
CID:828129
PubChem ID:44754897
Update Time:2025-06-16

3-Dimethylaminophenylboronic acid, hydrochloride Chemical and Physical Properties

Names and Identifiers

    • 3-(N,N-Dimethylamino)phenylboronic acid hydrochloride
    • 3-(Dimethylamino)phenylboronic Acid Hydrochloride (contains varying amounts of Anhydride)
    • 3-(Dimethylamino)phenylboronic acid hydrochloride
    • (3-(Dimethylamino)phenyl)boronic acid hydrochloride
    • 3-Dimethylaminophenylboronic acid, HCl
    • [3-(dimethylamino)phenyl]boronic acid,hydrochloride
    • 3-(Dimethylamino)benzeneboronic Acid Hydrochloride
    • 3-(Dimethylamino)benzeneboronic Acid Hydrochloride (contains varying amounts of Anhydride)
    • 3-Dimethylaminophenylboronic acid, hydrochloride
    • MDL: MFCD04112542
    • Inchi: 1S/C8H12BNO2.ClH/c1-10(2)8-5-3-4-7(6-8)9(11)12;/h3-6,11-12H,1-2H3;1H
    • InChI Key: QDYZZIRCCVRLBI-UHFFFAOYSA-N
    • SMILES: Cl.OB(C1=CC=CC(=C1)N(C)C)O

Computed Properties

  • Exact Mass: 201.07300
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2

Experimental Properties

  • PSA: 43.70000
  • LogP: 0.23440

3-Dimethylaminophenylboronic acid, hydrochloride Security Information

3-Dimethylaminophenylboronic acid, hydrochloride Customs Data

  • HS CODE:2931900090
  • Customs Data:

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

3-Dimethylaminophenylboronic acid, hydrochloride Pricemore >>

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Additional information on 3-Dimethylaminophenylboronic acid, hydrochloride

Introduction to 3-Dimethylaminophenylboronic Acid, Hydrochloride (CAS No: 1256355-23-3)

3-Dimethylaminophenylboronic acid, hydrochloride, identified by the Chemical Abstracts Service Number (CAS No) 1256355-23-3, is a specialized organoboron compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound, featuring a boronic acid functional group attached to a dimethylamino-substituted phenyl ring, exhibits unique chemical properties that make it a valuable intermediate in synthetic applications and a promising candidate for various biomedical research endeavors.

The structure of 3-Dimethylaminophenylboronic acid, hydrochloride consists of a phenyl ring substituted with two methyl groups on the nitrogen atom and a boronic acid moiety at the para position relative to the dimethylamino group. This particular arrangement imparts distinct reactivity and solubility characteristics, which are exploited in multiple industrial and research applications. The hydrochloride salt form enhances its solubility in aqueous systems, making it more amenable for use in solution-based reactions and formulations.

In recent years, boronic acids have emerged as pivotal compounds in medicinal chemistry due to their ability to form stable complexes with diols and other polyhydroxy compounds. This property is particularly relevant in the context of glycosylation reactions, where 3-Dimethylaminophenylboronic acid, hydrochloride serves as an effective catalyst or intermediate. The dimethylamino group further influences the electronic environment of the boronic acid, potentially enhancing its affinity for specific biological targets.

One of the most notable applications of 3-Dimethylaminophenylboronic acid, hydrochloride is in the development of targeted drug delivery systems. Boron-containing compounds have been extensively studied for their potential use in boron neutron capture therapy (BNCT), a novel approach to cancer treatment that leverages the selective accumulation of boron compounds in tumor tissues. The unique structural features of this compound make it an attractive candidate for such therapeutic strategies, as it can be engineered to exhibit high selectivity and low toxicity.

Recent advancements in synthetic methodologies have enabled the efficient preparation of 3-Dimethylaminophenylboronic acid, hydrochloride, facilitating its integration into diverse chemical processes. Researchers have demonstrated its utility in cross-coupling reactions, where it acts as a ligand or intermediate to facilitate the formation of carbon-carbon bonds. These reactions are fundamental to the synthesis of complex organic molecules, including pharmaceuticals and fine chemicals.

The pharmacological potential of 3-Dimethylaminophenylboronic acid, hydrochloride has also been explored in the context of enzyme inhibition and receptor binding studies. Its ability to interact with biological molecules makes it a valuable tool for investigating mechanisms of action and developing new therapeutic agents. For instance, studies have shown that derivatives of this compound can modulate the activity of enzymes involved in metabolic pathways relevant to diseases such as diabetes and cancer.

In addition to its pharmaceutical applications, 3-Dimethylaminophenylboronic acid, hydrochloride finds utility in materials science, particularly in the development of organic electronic materials. Boron-containing aromatic compounds often exhibit enhanced stability and electronic properties, making them suitable for use in semiconductors, conductive polymers, and other advanced materials. The dimethylamino group can further tune these properties by influencing electron delocalization and charge transport characteristics.

The synthesis of 3-Dimethylaminophenylboronic acid, hydrochloride typically involves multi-step organic transformations starting from readily available precursors. Advances in catalytic techniques have streamlined these processes, reducing reaction times and improving yields. Such improvements are crucial for scaling up production and making this compound more accessible for industrial applications.

From a regulatory perspective, 3-Dimethylaminophenylboronic acid, hydrochloride is subject to standard chemical safety protocols due to its reactivity and potential health effects. Proper handling procedures must be followed to ensure worker safety and environmental compliance. However, its classification does not place it under stringent regulatory controls related to hazardous substances or controlled drugs.

The future prospects for 3-Dimethylaminophenylboronic acid, hydrochloride are promising, with ongoing research exploring new applications and refining existing ones. As our understanding of molecular interactions deepens, this compound is expected to play an increasingly important role in drug discovery and material innovation. Collaborative efforts between academia and industry will be essential to fully realize its potential across multiple disciplines.

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