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Classification | Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives |
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Name | Ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate |
Synonyms | Ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate; Ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate; Ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate |
Molecular Structure | ![]() |
Molecular Formula | C11H19BO4 |
Molecular Weight | 226.08 |
CAS Registry Number | 1009307-13-4 |
EC Number | 805-282-6 |
SMILES | B1(OC(C(O1)(C)C)(C)C)/C=C/C(=O)OCC |
Density | 1.0±0.1 g/cm3 Calc.* |
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Boiling point | 236.8±42.0 ºC 760 mmHg (Calc.)* |
Flash point | 97.0±27.9 ºC (Calc.)* |
Index of refraction | 1.446 (Calc.)* |
* | Calculated using Advanced Chemistry Development (ACD/Labs) Software. |
Hazard Symbols |
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Hazard Statements | H302-H312-H315-H319-H332-H335 Details | ||||||||||||||||||||||||||||||||||||
Precautionary Statements | P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501 Details | ||||||||||||||||||||||||||||||||||||
Hazard Classification | |||||||||||||||||||||||||||||||||||||
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Ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate, also known as ethyl trans-3-(pinacolboronate)-acrylate, is a boron-containing compound that plays an important role in the field of synthetic organic chemistry. This compound is categorized as a boronic ester and incorporates the pinacol boronic ester moiety, which is widely recognized for its utility in cross-coupling reactions, particularly the Suzuki–Miyaura coupling. The molecular structure includes an α,β-unsaturated ester system conjugated with the boronic ester group, giving it valuable properties for chemical transformations. The synthesis of this compound can be traced to the development of methods for the preparation of functionalized boronic esters in the late 20th century. Pinacolborane derivatives gained attention for their stability and reactivity, and among them, the combination of pinacolborane with activated olefins, such as α,β-unsaturated esters, enabled the production of versatile intermediates like ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate. The use of hydroboration techniques followed by esterification with ethyl acrylate or the direct borylation of ethyl cinnamate derivatives represents established methods for preparing this molecule. These reactions typically involve catalysts such as iridium or palladium complexes, enabling selective formation of the E-isomer of the desired product. In terms of chemical applications, this compound serves primarily as a building block for the formation of C–C bonds via palladium-catalyzed cross-coupling reactions. It participates efficiently in Suzuki–Miyaura reactions, which are a cornerstone of modern organic synthesis. These transformations enable the construction of substituted alkenes, aromatic rings, and heterocycles, which are foundational structures in medicinal chemistry, agrochemical development, and materials science. The ester functionality allows for additional functionalization or transformation post-coupling, making the molecule particularly useful in multi-step synthesis strategies. Another area of application includes its role as a precursor for synthesizing more complex boron-containing molecules. The boronic ester group in this compound is known for its stability under ambient conditions, but it can also undergo hydrolysis to yield the corresponding boronic acid, which is another key reagent in organic chemistry. Moreover, the compound has been used in the preparation of conjugated polymers and other extended π-systems where controlled introduction of electron-withdrawing ester groups and boron atoms is desirable for tuning electronic properties. This compound is also relevant in the context of enantioselective synthesis and organometallic chemistry. Some of its derivatives have been investigated for their role in asymmetric catalysis, where the geometry of the alkene and the steric hindrance from the pinacol group can influence the stereochemical outcome of subsequent reactions. The compound’s reactivity profile has made it a useful test substrate in the development of new catalytic systems, particularly those based on transition metals such as palladium, nickel, and copper. In addition, ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate has found use in the preparation of fluorinated and trifluoromethylated alkenes. These transformations are significant due to the prominence of fluorinated functional groups in pharmaceuticals and agrochemicals. The presence of both the boron and ester functionalities facilitates selective transformation under mild conditions, allowing for compatibility with sensitive substrates. Overall, the compound has become a staple in the chemist’s toolkit for C–C bond formation and has contributed to the development of efficient, selective, and modular synthetic methods. Its stability, ease of handling, and broad compatibility with diverse reaction conditions underscore its continued relevance in laboratory and industrial settings. References 2020. Synthesis of Parsaclisib. Synfacts, DOI: 10.1055/s-0039-1691435 2019. Miyaura Borylation of Aryl Halides in Water. Science of Synthesis, URL: https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0039-1691435 2017. Synthesis of an HIV-1 Protease Inhibitor. Synfacts, DOI: 10.1055/s-0036-1590680 |
Market Analysis Reports |
List of Reports Available for Ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate |