Description

4-Chloropyridine-3-boronic acid, pinacol ester (CAS No. 452972-15-5) is a high-purity boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. This compound, with the molecular formula C₁₁H₁₅BClNO₂, is a stable and versatile building block for synthesizing complex heterocyclic compounds in pharmaceutical and agrochemical research. Its IUPAC name, 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, reflects its pinacol-protected boronic acid functionality, which enhances shelf stability and handling convenience. Ideal for researchers seeking reliable intermediates for C-C bond formation, this product is rigorously tested for quality, ensuring optimal performance in catalytic applications. Available in various quantities, it is packaged under inert conditions to maintain integrity.

Properties

• CAS Number: 452972-15-5
• Complexity: 257
• IUPAC Name: 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• InChI: InChI=1S/C11H15BClNO2/c1-10(2)11(3,4)16-12(15-10)8-7-14-6-5-9(8)13/h5-7H,1-4H3
• InChI Key: KTLJNRVZMVZXMR-UHFFFAOYSA-N
• Exact Mass: 239.0884366
• Molecular Formula: C11H15BClNO2
• Molecular Weight: 239.51
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CN=C2)Cl
• Topological: 31.4
• Monoisotopic Mass: 239.0884366
• Synonyms: 4-Chloropyridine-3-boronic acid, pinacol ester, 670-325-6, 452972-15-5, 4-Chloropyridine-3-boronic acid pinacol ester, 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, MFCD06798247, 4-Chloropyridin-3-ylboronic acid, pinacol ester, 4-chloro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 4-Chloropyridine-3-boronicAcidPinacolEster, Pyridine, 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, SCHEMBL166233, (4-CHLOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER, DTXSID00476867, KTLJNRVZMVZXMR-UHFFFAOYSA-N, BBL103164, STL556974, AKOS015949908, AB29854, GS-6280, SY023186, CS-0054405, A25354, EN300-191084, Z3234953204, 4-CHLOROPYRIDIN-3-YLBORONIC ACID, PINACOL ESTER 98, 4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-pyridine, 4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine

Application

4-Chloropyridine-3-boronic acid, pinacol ester is a key reagent in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl and heteroaryl structures. It is particularly valuable in medicinal chemistry for constructing pyridine-based scaffolds in drug discovery. The compound’s stability and reactivity make it suitable for iterative coupling strategies in complex molecule synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (13.3%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (13.3%): 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 (13.3%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (13.3%)

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