Cas no 17136-80-0 (METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE)

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. Its key advantages include high stability under ambient conditions, facilitating handling and storage. The presence of the pinacol boronate group enhances reactivity with aryl halides, enabling efficient C-C bond formation in synthetic organic chemistry. The methyl ester moiety provides additional versatility for further functionalization. This compound is particularly valuable in pharmaceutical and materials science research, where precise boronation is required. Its crystalline solid form ensures consistent purity, making it a reliable reagent for complex synthetic pathways.
METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE structure
17136-80-0 structure
Product Name:METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
CAS No:17136-80-0
MF:C14H19BO4
MW:262.109264612198
CID:94897
PubChem ID:2773500
Update Time:2025-06-12

METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE Chemical and Physical Properties

Names and Identifiers

    • METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
    • 2-(4-CARBOMETHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
    • 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)BENZOIC ACID METHYL ESTER
    • 4-METHOXYCARBONYLPHENYLBORONIC ACID PINACOLATE
    • (4-Methoxycarbonylphenyl)boronic acid
    • 4-Methoxycarbonylphenylboronic acid pinacol ester
    • Methyl 4-((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)Methyl)benzoate
    • CS-W000882
    • 2-(4-Methoxycarbonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • (4-methoxycarbonylphenyl)boronic acid, pinacol ester
    • 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID METHYL ESTER
    • (4-(METHOXYCARBONYL)PHENYL)BORONIC ACID PINACOL ESTER
    • Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -yl)benzoate
    • 10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N.1
    • SCHEMBL105161
    • 4-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-benzoic acid methyl ester
    • methyl?4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • A811322
    • 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester
    • EN300-336124
    • 171364-80-0
    • 4-Methoxycarbonylbenzeneboronic acid pinacol ester
    • AB11131
    • M3057
    • MFCD02179438
    • SY003286
    • methyl4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzoate
    • AKOS000283812
    • 4-Methoxycarbonylphenylboronic acid pinacol ester, 97%
    • DTXSID10378500
    • 4-(methoxycarbonyl)benzeneboronic acid pinacol ester
    • doi:10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N
    • AS-2266
    • 4-(methoxycarbonyl)phenylboronic acid pinacol ester
    • Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzoate (4-Methoxycarbonylphenylboronic acid pinacol ester)
    • J-522081
    • FT-0643640
    • 17136-80-0
    • J-010720
    • AM62748
    • 4-Methoxycarbonylphenylboronic acid, pinacol ester
    • J-522239
    • methyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • 10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N
    • Benzoic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester
    • 4-Carbomethoxyphenylboronic acid pinacol ester
    • Methyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • REIZEQZILPXYKS-UHFFFAOYSA-N
    • doi:10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N.1
    • DB-016166
    • Inchi： 1S/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)11-8-6-10(7-9-11)12(16)17-5/h6-9H,1-5H3
    • InChI Key： REIZEQZILPXYKS-UHFFFAOYSA-N
    • SMILES： O1B(C2C=CC(C(=O)OC)=CC=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 261.14127
  • Monoisotopic Mass: 262.1376392g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 3
  • Complexity: 329
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 44.8?2

Experimental Properties

  • Density: 1.08
  • Melting Point: 77-81?°C(lit.)
  • Boiling Point: 355.6°Cat760mmHg
  • Flash Point: 168.8°C
  • PSA: 44.76
  • LogP: 1.77240

METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE Security Information

  • WGK Germany：3

METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE Pricemore >>

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METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE Related Literature

Additional information on METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE

Comprehensive Overview of METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE (CAS No. 17136-80-0)

METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE (CAS No. 17136-80-0) is a highly versatile boronic ester derivative widely utilized in organic synthesis, pharmaceutical research, and material science. This compound, often referred to as a pinacol boronic ester, is a critical intermediate in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern drug discovery and agrochemical development. Its unique structure, featuring a benzoate moiety and a dioxaborolane ring, enables efficient C-C bond formation, making it indispensable for constructing complex biaryl compounds.

The growing demand for METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE is driven by its applications in targeted drug delivery systems and bioconjugation. Researchers are increasingly exploring its role in proteolysis-targeting chimeras (PROTACs), a revolutionary approach in cancer therapy. Additionally, its stability under mild conditions and compatibility with green chemistry principles align with the global push for sustainable synthesis methods. This compound’s relevance in OLED materials and organic electronics further underscores its multidisciplinary importance.

From a synthetic perspective, METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE offers exceptional functional group tolerance, allowing chemists to design highly selective reactions. Its boronate group acts as a transient protecting group, enabling sequential modifications of aromatic systems. Recent studies highlight its utility in late-stage diversification of pharmaceuticals, addressing challenges in personalized medicine. The compound’s crystalline stability and ease of purification also make it a preferred choice for industrial-scale production.

In the context of AI-driven drug discovery, METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE is frequently cited in cheminformatics databases due to its predictable reactivity patterns. Its SMILES notation and molecular descriptors are integral to machine learning models predicting reaction outcomes. Furthermore, its compatibility with flow chemistry setups resonates with the trend toward automated synthesis platforms, reducing waste and improving reproducibility.

Environmental and regulatory considerations are paramount for METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE. Its low ecotoxicity profile and compliance with REACH guidelines position it favorably for large-scale applications. As industries prioritize circular economy principles, this compound’s potential for catalytic recycling is under active investigation. Innovations in biodegradable boron reagents may further enhance its sustainability footprint.

For researchers seeking high-purity METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE, advanced analytical techniques such as HPLC and NMR spectroscopy ensure batch consistency. Storage recommendations typically emphasize anhydrous conditions to prevent hydrolysis of the boronate ester. Suppliers often provide custom synthesis services to meet specific research needs, reflecting the compound’s adaptability to diverse chemical space exploration.

In summary, METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE (CAS No. 17136-80-0) exemplifies the intersection of innovation and practical utility in modern chemistry. Its role in advancing precision medicine, smart materials, and sustainable processes ensures its enduring relevance. As scientific frontiers expand, this compound will undoubtedly remain a keystone in the toolkit of 21st-century chemists.

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