Description

3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (CAS No. 719268-92-5) is a high-purity boronic ester derivative with the molecular formula C₁₁H₁₅BFNO₂. This compound features a pyridine ring substituted with a fluorine atom at the 3-position and a pinacol boronate ester at the 5-position, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions. Its stability under anhydrous conditions and compatibility with various organic solvents enhance its utility in synthetic organic chemistry. Ideal for pharmaceutical research, agrochemical development, and materials science, this reagent is rigorously tested for quality (≥95% purity by HPLC) and supplied in moisture-resistant packaging to ensure optimal performance.

Properties

• CAS Number: 719268-92-5
• Complexity: 257
• IUPAC Name: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• InChI: InChI=1S/C11H15BFNO2/c1-10(2)11(3,4)16-12(15-10)8-5-9(13)7-14-6-8/h5-7H,1-4H3
• InChI Key: VFMTUTYBMBTIGA-UHFFFAOYSA-N
• Exact Mass: 223.1179870
• Molecular Formula: C11H15BFNO2
• Molecular Weight: 223.05
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CN=C2)F
• Topological: 31.4
• Monoisotopic Mass: 223.1179870
• Synonyms: 3-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 805-081-3, 719268-92-5, 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 3-Fluoropyridine-5-boronic acid pinacol ester, 5-Fluoropyridine-3-boronic acid, pinacol ester, 5-Fluoropyridine-3-boronic acid pinacol ester, MFCD07780754, C11H15BFNO2, 3-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine, 3-Fluoropyridine-5-boronic acid, pinacol ester, (5-FLUOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER, 3-Fluoro-5-(4455-tetramethyl-132-dioxaborolan-2-yl)pyridine, 3-Fluoropyridine-5-boronic acid pinacol eater, SCHEMBL975905, SCHEMBL22319213, DTXSID50585993, VFMTUTYBMBTIGA-UHFFFAOYSA-N, SBB096425, AKOS015842141, AB42551, NCGC00662821-01, AC-33452, DS-14891, SY025633, DB-050588, CS-0109834, F1026, 5-Fluoro-3-pyridylboronic Acid Pinacol Ester, EN300-160485, Z1336745108, 2-(5-fluoro(3-pyridyl))-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(5-Fluoro-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 5-fluoropyridin-3-ylboronate, 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, AldrichCPR, 3-Fluoro-5-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)pyridine

Application

3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is widely used as a key building block in Suzuki-Miyaura cross-coupling reactions to introduce fluoropyridine motifs into complex molecules. It is particularly valuable in medicinal chemistry for the synthesis of bioactive compounds, including kinase inhibitors and CNS-targeting drugs. The fluorine substitution enhances metabolic stability and binding affinity in drug candidates. Researchers also employ this reagent in material science to develop fluorinated conjugated polymers for optoelectronic applications.

Safety and Hazards

GHS Hazard Statements

• H315 (75%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (75%): 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, 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 (75%)
• Eye Irrit. 2 (75%)
• STOT SE 3 (50%)

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