Description

(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (CAS: 1009307-13-4) is a high-purity boronic ester derivative widely utilized in organic synthesis and pharmaceutical research. This compound, with the molecular formula C₁₁H₁₉BO₄, features a reactive vinylboronate group protected by a pinacol ester, making it an excellent intermediate for Suzuki-Miyaura cross-coupling reactions. Its (E)-configuration ensures stereochemical stability, while the ethyl acrylate moiety enhances solubility and reactivity in diverse solvents. Ideal for constructing complex organic frameworks, this reagent is rigorously tested for quality (≥95% purity by HPLC) and supplied in moisture-resistant packaging to ensure optimal performance. Researchers value its compatibility with palladium catalysts and its role in synthesizing conjugated systems for materials science and drug discovery.

Properties

• CAS Number: 1009307-13-4
• Complexity: 280
• IUPAC Name: ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate
• InChI: 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
• Exact Mass: 226.1376392
• Molecular Formula: C11H19BO4
• Molecular Weight: 226.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C(=O)OCC
• Topological: 44.8
• Monoisotopic Mass: 226.1376392
• Synonyms: 1009307-13-4, (E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate, 1263187-14-9, ethyl (2Z)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate, 805-282-6, 960-357-1, Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate, 3-Ethoxy-3-oxo-1-propene-1-boronic Acid Pinacol Ester, 2-(ETHOXYCARBONYL)VINYLBORONIC ACID PINACOL ESTER, 2-Propenoic acid, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester, (2E)-, (E)-2-Ethoxycarbonylvinylboronic acid pinacol ester, ethyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate, [(E)-2-(ETHOXYCARBONYL)VINYL]BORONIC ACID, PINACOL ESTER, ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate, MFCD09027313, 2-Propenoic acid, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester, ZXDDITJXZPTHFE-BQYQJAHWSA-N, SCHEMBL1823662, (E)-(3-ETHOXY-3-OXOPROP-1-EN-1-YL)BORONIC ACID PINACOL ESTER, AKOS015843289, CS-12556, DS-14124, CS-0063246, D73291, EN300-200129, EN300-1654191, 2-ETHOXYCARBONYLVINYLBORONICACIDPINACOLESTER, ((E)-2-(Ethoxycarbonyl)vinyl)boronic acid pinacol ester, Z2315579780, (E)-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate, (E)-Ethyl3-(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-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PROP-2-ENOATE, Ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate

This compound is primarily employed in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds, enabling the synthesis of biaryl and styrene derivatives. It serves as a key building block in pharmaceutical intermediates and agrochemicals. The pinacol boronate group offers enhanced stability and reactivity under mild conditions. Applications extend to materials science for creating π-conjugated polymers. Suitable for use in anhydrous environments with palladium catalysts like Pd(PPh₃)₄.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (66.7%)
• Acute Tox. 4 (33.3%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• Acute Tox. 4 (66.7%)
• STOT SE 3 (100%)

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