Description

(3-Acetamidophenyl)boronic acid (CAS No. 78887-39-5) is a high-purity boronic acid derivative with the molecular formula C₈H₁₀BNO₃. This compound features an acetamido group at the meta position of the phenyl ring, enhancing its utility in organic synthesis and pharmaceutical research. With a molecular weight of 178.98 g/mol, it is a white to off-white crystalline powder that is soluble in common organic solvents such as DMSO, methanol, and ethanol. (3-Acetamidophenyl)boronic acid is widely employed as a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex molecule synthesis. Its stability and reactivity make it a valuable reagent for researchers in medicinal chemistry, material science, and catalysis. Store in a cool, dry place under inert conditions to ensure long-term stability.

Properties

• CAS Number: 78887-39-5
• Complexity: 186
• IUPAC Name: (3-acetamidophenyl)boronic acid
• InChI: InChI=1S/C8H10BNO3/c1-6(11)10-8-4-2-3-7(5-8)9(12)13/h2-5,12-13H,1H3,(H,10,11)
• InChI Key: IBTSWKLSEOGJGJ-UHFFFAOYSA-N
• Exact Mass: 179.0753733
• Molecular Formula: C8H10BNO3
• Molecular Weight: 178.98
• SMILES: B(C1=CC(=CC=C1)NC(=O)C)(O)O
• Topological: 69.6
• Monoisotopic Mass: 179.0753733
• Synonyms: (3-acetamidophenyl)boronic acid, 671-843-5, 3-Acetamidophenylboronic acid, 78887-39-5, 3-Acetylaminophenylboronic acid, 3-Acetamidobenzeneboronic acid, MFCD00236013, (3-acetylaminophenyl)boronic acid, 3-(acetylamino)phenylboronic acid, Boronic acid, (3-(acetylamino)phenyl)-, Boronic acid, [3-(acetylamino)phenyl]-, Boronic acid, B-[3-(acetylamino)phenyl]-, (3-(acetylamino)phenyl)boronic acid, [3-(acetylamino)phenyl]boronic acid, 3-Acetamidophenylboronicacid, 3-acetylaminophenyl boronic acid, SCHEMBL8930, 3-acet-amidophenylboronic acid, 3-acetamidophenyl boronic acid, 3-acetamidophenyl-boronic acid, 3-acetaminophenyl boronic acid, 3-(acetamido)phenylboronic acid, 3-acetamido phenyl boronic acid, 3-acetamido-phenyl boronic acid, 3-acetamidophenyl- boronic acid, 3-acetamino-phenyl boronic acid, 3-acetylamino-phenylboronic acid, DTXSID1074678, SCHEMBL11349846, (3-acetamidophenyl) boronic acid, IBTSWKLSEOGJGJ-UHFFFAOYSA-N, 3-(acetylamino) phenylboronic acid, BCP03527, CS-D0989, STR07962, 3-(N-acetylamino)phenylboronic acid, SBB000203, AKOS006223915, 3-ACETAMIDOBENZENE BORONIC ACID, AB05328, BP-20139, SY023416, DB-010521, A2453, EN300-316448, Z1203161678, 3-Acetamidophenylboronic Acid (contains varying amounts of Anhydride)

Application

(3-Acetamidophenyl)boronic acid is primarily used as a versatile building block in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl compounds. It serves as a critical intermediate in pharmaceutical research, particularly in the development of kinase inhibitors and other bioactive molecules. Additionally, this compound finds applications in material science for the preparation of functionalized polymers and advanced organic frameworks. Its boronic acid moiety also enables its use in sensor development for detecting diols and saccharides.

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 (88.9%): 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. 2A (100%)
• STOT SE 3 (88.9%)

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