Description

2-Aminopyridine-4-boronic acid pinacol ester (CAS: 1195995-72-2) is a high-purity boronic ester derivative with the molecular formula C₁₁H₁₇BN₂O₂. This compound, also known by its IUPAC name 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, is a valuable building block in organic synthesis and pharmaceutical research. The pinacol ester group enhances stability and solubility, making it ideal for Suzuki-Miyaura cross-coupling reactions. Its structure features a reactive boronate moiety and an amino group, enabling diverse functionalization. Suitable for researchers in medicinal chemistry, this compound is rigorously tested for quality and supplied with detailed analytical data (NMR, HPLC, MS). Store under inert conditions to maintain integrity.

Properties

• CAS Number: 1195995-72-2
• Complexity: 255
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
• InChI: InChI=1S/C11H17BN2O2/c1-10(2)11(3,4)16-12(15-10)8-5-6-14-9(13)7-8/h5-7H,1-4H3,(H2,13,14)
• InChI Key: DCYKWKYBNWRLLZ-UHFFFAOYSA-N
• Exact Mass: 220.1383080
• Molecular Formula: C11H17BN2O2
• Molecular Weight: 220.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=NC=C2)N
• Topological: 57.4
• Monoisotopic Mass: 220.1383080
• Synonyms: 2-AMINOPYRIDINE-4-BORONIC ACID PINACOL ESTER, 689-089-0, 1195995-72-2, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, 2-Pyridinamine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, MFCD09607735, (2-AMINOPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER, 2-Aminopyridine-4-boronic acid, pinacol ester, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine, SCHEMBL614168, DTXSID00671294, DCYKWKYBNWRLLZ-UHFFFAOYSA-N, AKOS015947245, AB50841, AS-32703, SY028254, DB-061580, CS-0020016, 2-Amino-4-pyridineboronic acid, pinacol ester, EN300-53506, 2-Aminopyridine-4-boronic acid, pinacol ester, >=97%, 2-Aminopyridine-4-boronic acid, pinacol ester, AldrichCPR

Application

2-Aminopyridine-4-boronic acid pinacol ester is widely used in palladium-catalyzed cross-coupling reactions to synthesize biaryl compounds for drug discovery. It serves as a key intermediate in the development of kinase inhibitors and other heterocyclic pharmaceuticals. The amino group allows further derivatization, enabling tailored modifications for target-specific applications. Its stability under mild conditions makes it suitable for multi-step synthetic routes. Researchers also employ it in materials science for constructing boron-containing conjugated systems.

Safety and Hazards

GHS Hazard Statements

• H301 (33.3%): Toxic if swallowed [Danger Acute toxicity, oral]
• H302+H312+H332 (16.7%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (83.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (33.3%)
• Skin Irrit. 2 (50%)
• Eye Irrit. 2 (83.3%)
• STOT SE 3 (50%)

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