Cas no 1263187-14-9 (3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester)

3-Ethoxy-3-oxo-1-propene-1-boronic acid pinacol ester is a specialized boronic ester derivative used in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. Its α,β-unsaturated ester functionality enhances reactivity, enabling efficient carbon-carbon bond formation with aryl or vinyl halides. The pinacol ester group improves stability, facilitating handling and storage while maintaining compatibility with mild reaction conditions. This compound is valuable in constructing complex molecules, including pharmaceuticals and agrochemicals, due to its selectivity and functional group tolerance. Its structural features make it a versatile intermediate for synthesizing conjugated systems and other advanced frameworks. Proper handling under inert conditions is recommended to preserve reactivity.
3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester structure
1263187-14-9 structure
Product Name:3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester
CAS No:1263187-14-9
MF:C11H19BO4
MW:226.077163934708
MDL:MFCD09027313
CID:1027004
PubChem ID:23553751
Update Time:2025-05-26

3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester Chemical and Physical Properties

Names and Identifiers

    • (E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
    • Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
    • 2-Benzamino-benzoesaeure-aethylester
    • ethoxycarbonylvinylboronic acid pinacolester
    • N-benzoyl-anthranilic acid ethyl ester
    • N-Benzoylanthranilsaeureaethylester
    • J-000275
    • ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
    • 2-ETHOXYCARBONYLVINYLBORONICACIDPINACOLESTER
    • Z2315579780
    • ZXDDITJXZPTHFE-BQYQJAHWSA-N
    • (E)-2-Ethoxycarbonylvinylboronic acid pinacol ester
    • A897293
    • A889458
    • D73291
    • MFCD09027313
    • EN300-1654191
    • CS-12556
    • AKOS015843289
    • 2-Propenoic acid, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester, (2E)-
    • ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate
    • 1009307-13-4
    • Ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate
    • DS-14124
    • [(E)-2-(ETHOXYCARBONYL)VINYL]BORONIC ACID, PINACOL ESTER
    • (E)-Ethyl3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
    • 2-ETHOXYCARBONYLVINYLBORONIC ACID PINACOL ESTER
    • 2-Propenoic acid, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester
    • 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester
    • SCHEMBL1823662
    • CS-0063246
    • (E)-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
    • 1263187-14-9
    • 2-(ETHOXYCARBONYL)VINYLBORONIC ACID PINACOL ESTER
    • ethyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate
    • EN300-200129
    • ETHYL (2E)-3-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PROP-2-ENOATE
    • (E)-(3-ETHOXY-3-OXOPROP-1-EN-1-YL)BORONIC ACID PINACOL ESTER
    • ((E)-2-(Ethoxycarbonyl)vinyl)boronic acid pinacol ester
    • MDL: MFCD09027313
    • Inchi: 1S/C11H19BO4/c1-6-14-9(13)7-8-12-15-10(2,3)11(4,5)16-12/h7-8H,6H2,1-5H3/b8-7+
    • InChI Key: ZXDDITJXZPTHFE-BQYQJAHWSA-N
    • SMILES: O1B(/C=C/C(=O)OCC)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 226.13800
  • Monoisotopic Mass: 226.1376392g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 280
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 44.8?2

Experimental Properties

  • PSA: 44.76000
  • LogP: 1.73710

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Additional information on 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester

3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester (CAS No. 1263187-14-9): An Overview

3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester (CAS No. 1263187-14-9) is a versatile compound that has gained significant attention in the fields of organic synthesis and medicinal chemistry. This boronic ester derivative is particularly valuable due to its reactivity and stability, making it an essential reagent in various synthetic transformations and cross-coupling reactions.

The chemical structure of 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester features a boronic acid pinacol ester moiety attached to a propenone framework. The presence of the boronic acid pinacol ester group imparts unique reactivity and functional group compatibility, which are crucial for its applications in modern synthetic chemistry.

In recent years, the use of boronic esters in organic synthesis has been extensively explored, particularly in the context of Suzuki-Miyaura coupling reactions. These reactions are widely employed in the synthesis of biologically active compounds, pharmaceuticals, and materials science. The 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester is no exception, as it has demonstrated excellent performance in these coupling reactions, facilitating the formation of carbon-carbon bonds under mild conditions.

The stability of 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester under various reaction conditions is another key attribute that sets it apart from other boronic esters. This stability ensures that the compound remains reactive and does not decompose easily, which is crucial for maintaining high yields and selectivity in synthetic processes. Additionally, its solubility in common organic solvents such as dichloromethane, tetrahydrofuran, and dimethylformamide makes it easy to handle and integrate into existing synthetic protocols.

In the realm of medicinal chemistry, 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester has shown promise as a building block for the synthesis of novel drug candidates. Its ability to form stable intermediates and participate in multi-step syntheses makes it an attractive choice for researchers working on the development of new therapeutic agents. For instance, recent studies have demonstrated its utility in the synthesis of anti-cancer drugs and anti-inflammatory compounds.

The versatility of 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester extends beyond its use as a reagent in organic synthesis. It has also found applications in materials science, where it is used to modify surfaces and create functional coatings with enhanced properties. The ability to introduce boron-containing functionalities onto surfaces can lead to improved adhesion, corrosion resistance, and biocompatibility, which are highly desirable in various industrial and biomedical applications.

In conclusion, 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester (CAS No. 1263187-14-9) is a highly valuable compound with a wide range of applications in organic synthesis, medicinal chemistry, and materials science. Its unique chemical properties, including reactivity, stability, and functional group compatibility, make it an indispensable tool for researchers and chemists working in these fields. As research continues to advance, it is likely that new applications and uses for this compound will be discovered, further solidifying its importance in modern chemistry.

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