Description

(3-Ethoxycarbonylphenyl)boronic acid (CAS No. 4334-87-6) is a high-purity boronic acid derivative with the molecular formula C₉H₁₁BO₄. This compound features an ethoxycarbonyl functional group at the meta-position of the phenyl ring, making it a versatile building block for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. With a molecular weight of 194.00 g/mol, it is supplied as a white to off-white crystalline powder, ensuring excellent solubility in common organic solvents such as THF, DMF, and DMSO. Ideal for pharmaceutical research, material science, and organic synthesis, this reagent is rigorously tested for purity (typically ≥95% by HPLC or NMR) and stability under recommended storage conditions (2-8°C, inert atmosphere). Suitable for use in high-throughput screening, medicinal chemistry, and as a key intermediate in the synthesis of complex molecules.

Properties

• CAS Number: 4334-87-6
• Complexity: 195
• IUPAC Name: (3-ethoxycarbonylphenyl)boronic acid
• InChI: InChI=1S/C9H11BO4/c1-2-14-9(11)7-4-3-5-8(6-7)10(12)13/h3-6,12-13H,2H2,1H3
• InChI Key: REHVCPNQQBDOJJ-UHFFFAOYSA-N
• Exact Mass: 194.0750390
• Molecular Formula: C9H11BO4
• Molecular Weight: 193.99
• SMILES: B(C1=CC(=CC=C1)C(=O)OCC)(O)O
• Topological: 66.8
• Monoisotopic Mass: 194.0750390
• Synonyms: (3-ethoxycarbonylphenyl)boronic Acid, 626-771-9, 3-Ethoxycarbonylphenylboronic acid, 4334-87-6, 3-(Ethoxycarbonyl)phenylboronic acid, (3-(ethoxycarbonyl)phenyl)boronic acid, MFCD02179444, m-ethoxycarbonylphenylboronic acid, 3-Ethoxycarbonylbenzeneboronic acid, BENZOIC ACID, 3-BORONO-, 1-ETHYL ESTER, [3-(ethoxycarbonyl)phenyl]boronic acid, 3-(ethoxycarbonyl)benzeneboronic acid, 3-carbethoxyphenylboronic acid, Ethyl 3-boronobenzoate, 3-Ethoxycarbonylphenylboronicacid, Ethyl 3-(Dihydroxyboranyl)Benzoate, 3-(ethoxycarbonyl)phenyl boronic acid, Phenylboronic Acid, 2, m-Carbethoxyphenylboronic acid, SCHEMBL361141, 3-carboethoxybenzeneboronic acid, CHEMBL488800, 3-(carbethoxy)phenylboronic acid, BDBM26123, DTXSID20390632, REHVCPNQQBDOJJ-UHFFFAOYSA-N, 63752S6NBJ, 3-ethoxycarbonyl-phenylboronic acid, 3-ethoxycarbonylphenyl boronic acid, 3-ethoxycarbonyl phenyl boronic acid, SBB052545, (3-ethoxycarbonylphenyl) boronic acid, 3-(ethoxycarbonyl)-phenylboronic acid, 3-(ethoxycarbonyl)phenyl-boronic acid, 3-CARBOETHOXYPHENYLBORONIC ACID, AKOS004116253, Benzoic acid, m-borono-, ethyl ester, AB11142, AC-6988, AS-3169, CS-W015758, HY-W015042, Benzoic acid, m-borono-, 1-ethyl ester, NCGC00249523-01, PD181022, SY014657, DB-010492, {3-[(ethyloxy)-carbonyl]phenyl}boronic acid, E0848, EN300-210125

Application

(3-Ethoxycarbonylphenyl)boronic acid is widely used as a coupling partner in Suzuki-Miyaura reactions to form biaryl compounds, a critical step in drug discovery and material science. Its boronic acid moiety enables efficient cross-coupling with aryl halides under palladium catalysis, facilitating the synthesis of complex organic frameworks. Researchers also employ it in the development of sensors and catalysts due to its ability to form reversible covalent bonds with diols and other Lewis bases.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

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

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.9%)

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