Description

4-Aminomethylphenylboronic acid pinacol ester (CAS No. 138500-88-6) is a highly versatile boronic acid derivative with the molecular formula C₁₃H₂₀BNO₂. This compound, also known as [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine, features a pinacol ester-protected boronic acid group, enhancing its stability and reactivity for Suzuki-Miyaura cross-coupling reactions. The aminomethyl moiety further expands its utility in bioconjugation, pharmaceutical synthesis, and materials science. With a purity grade suitable for research and industrial applications, this reagent is ideal for organic synthesis, medicinal chemistry, and catalyst development. Store under inert conditions to maintain optimal stability and performance.

Properties

• CAS Number: 138500-88-6
• Complexity: 257
• IUPAC Name: [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine
• InChI: InChI=1S/C13H20BNO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-8H,9,15H2,1-4H3
• InChI Key: FPUVAGQUKWMDKN-UHFFFAOYSA-N
• Exact Mass: 233.1587090
• Molecular Formula: C13H20BNO2
• Molecular Weight: 233.12
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)CN
• Topological: 44.5
• Monoisotopic Mass: 233.1587090
• Synonyms: 4-Aminomethylphenylboronic acid pinacol ester, 689-663-0, 138500-88-6, (4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine, 4-Aminomethylphenylboronic acid, pinacol ester, [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine, 4-(Aminomethyl)phenylboronic Acid Pinacol Ester, Benzenemethanamine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, MFCD06213229, 1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]METHANAMINE, (4-Aminomethylphenyl)boronic acid, pinacol ester, hydrochloride, SCHEMBL171778, FPUVAGQUKWMDKN-UHFFFAOYSA-N, [4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]METHANAMINE, AC1090, AKOS015999093, NCGC00662602-01, CS-11829, SY031071, DB-016031, CS-0130396, EN300-320247, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzylamine

Application

4-Aminomethylphenylboronic acid pinacol ester is widely used in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds in complex organic synthesis. Its bifunctional design enables conjugation with biomolecules, making it valuable for probe development and drug discovery. Researchers also employ it in the preparation of boron-containing polymers and advanced materials.

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 (100%): 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 (100%)

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