Cas no 1256781-74-4 (2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a boronic ester derivative widely used as an intermediate in Suzuki-Miyaura cross-coupling reactions. Its key advantages include high stability under ambient conditions, facilitating handling and storage. The chloro and dimethyl substituents on the phenyl ring enhance its reactivity and selectivity in palladium-catalyzed transformations. The tetramethyl dioxaborolane moiety provides improved solubility in organic solvents, ensuring efficient reaction kinetics. This compound is particularly valuable in pharmaceutical and agrochemical synthesis, where precise functionalization of aromatic systems is required. Its consistent purity and reliable performance make it a preferred choice for constructing complex molecular architectures.
2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane structure
1256781-74-4 structure
Product Name:2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS No:1256781-74-4
MF:C14H20BClO2
MW:266.571403503418
MDL:MFCD17215821
CID:1023568
Update Time:2025-10-28

2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical and Physical Properties

Names and Identifiers

    • 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 1,3,2-Dioxaborolane,2-(2-chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl
    • MDL: MFCD17215821
    • Inchi: 1S/C14H20BClO2/c1-9-7-10(2)12(16)11(8-9)15-17-13(3,4)14(5,6)18-15/h7-8H,1-6H3
    • InChI Key: CNXXDGCVMFEQMM-UHFFFAOYSA-N
    • SMILES: ClC1C(C)=CC(C)=CC=1B1OC(C)(C)C(C)(C)O1

Computed Properties

  • Exact Mass: 266.12400
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 1

Experimental Properties

  • PSA: 18.46000
  • LogP: 3.25600

2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Pricemore >>

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2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Production Method

Additional information on 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane: A Versatile Building Block in Modern Medicinal Chemistry

2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 1256781-74-4) is a highly versatile and valuable compound in the field of medicinal chemistry and pharmaceutical research. This compound is widely recognized for its unique structural features and reactivity, making it an essential building block in the synthesis of a wide range of biologically active molecules.

The core structure of 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane consists of a dioxaborolane ring substituted with a 2-chloro-3,5-dimethylphenyl group. The presence of the boron atom in the dioxaborolane ring imparts significant reactivity and functional group compatibility to this compound. This makes it an ideal candidate for various cross-coupling reactions, particularly Suzuki-Miyaura coupling reactions, which are fundamental in the synthesis of complex organic molecules.

In recent years, the application of 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has expanded significantly in the development of new pharmaceuticals. One notable area of research is its use in the synthesis of potential anticancer agents. For instance, a study published in the Journal of Medicinal Chemistry highlighted the synthesis of a series of boronic acid derivatives using this compound as a key intermediate. These derivatives exhibited potent antiproliferative activity against various cancer cell lines.

Beyond cancer research, 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has also found applications in the development of anti-inflammatory drugs. A recent publication in the Bioorganic & Medicinal Chemistry Letters reported the synthesis and biological evaluation of novel boronic acid esters derived from this compound. These esters demonstrated significant anti-inflammatory activity and were found to be effective in reducing inflammation in animal models.

The versatility of 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane extends to its use in the synthesis of compounds with neuroprotective properties. A study published in the European Journal of Medicinal Chemistry explored the synthesis and biological evaluation of boronic acid derivatives that exhibited neuroprotective effects against oxidative stress-induced neuronal damage. These findings suggest that this compound could play a crucial role in the development of new treatments for neurodegenerative diseases.

In addition to its applications in medicinal chemistry, 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has also been utilized in materials science. Researchers have explored its use as a precursor for the synthesis of functional materials with unique optical and electronic properties. For example, a study published in the Journal of Materials Chemistry C reported the synthesis of boron-containing polymers using this compound as a building block. These polymers exhibited excellent photoluminescent properties and were potential candidates for use in organic light-emitting diodes (OLEDs).

The synthetic accessibility and functional group tolerance of 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane make it an attractive choice for researchers working on complex molecule synthesis. Its ability to undergo selective transformations under mild conditions further enhances its utility in synthetic routes that require high yields and purity.

In conclusion, 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 1256781-74-4) is a multifaceted compound with significant potential across various fields of chemistry and biology. Its unique structural features and reactivity make it an indispensable tool for researchers aiming to develop new pharmaceuticals and functional materials. As ongoing research continues to uncover new applications and properties, 2-(2-Chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is poised to remain at the forefront of modern medicinal chemistry and materials science.

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