Description

1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester (CAS No. 454482-11-2) is a high-purity boronic ester derivative with the molecular formula C₁₂H₂₂BNO₂. This compound features a pinacol-protected boronate group attached to a 1-methyl-1,2,3,6-tetrahydropyridine scaffold, making it a valuable intermediate in organic synthesis and pharmaceutical research. Its IUPAC name is 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine. The pinacol ester group enhances stability and solubility, facilitating its use in Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed processes. This reagent is ideal for researchers developing novel heterocyclic compounds, drug candidates, or functional materials. Store under inert conditions to maintain reactivity and purity.

Properties

• CAS Number: 454482-11-2
• Complexity: 296
• IUPAC Name: 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine
• InChI: InChI=1S/C12H22BNO2/c1-11(2)12(3,4)16-13(15-11)10-6-8-14(5)9-7-10/h6H,7-9H2,1-5H3
• InChI Key: SQMVRFXDBRYXFQ-UHFFFAOYSA-N
• Exact Mass: 223.1743591
• Molecular Formula: C12H22BNO2
• Molecular Weight: 223.12
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCN(CC2)C
• Topological: 21.7
• Monoisotopic Mass: 223.1743591
• Synonyms: 1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester, 689-067-0, 454482-11-2, 1-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,2,3,6-TETRAHYDROPYRIDINE, 1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine, MFCD11506069, 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine, C12H22BNO2, SCHEMBL426356, DTXSID00609734, SQMVRFXDBRYXFQ-UHFFFAOYSA-N, BCP27927, 1-Methyl-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester, CS1509, (1-METHYL-1,2,3,6-TETRAHYDROPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER, AKOS015960288, AB64124, CS-W008881, DS-4338, AC-30051, SY059847, EN300-105806, Z1389476293, 1-methyl-1,2,3,6 tetrahydropyridine-4-boronic acid pinacol ester, 1-methyl-1,2,3,6-tetrahydropyridine-4 boronic acid pinacolester, 1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 97%, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine, 4,4,5,5-tetramethyl-2-(1-methyl(4-1,2,5,6-tetrahydropyridyl))-1,3,2-dioxaborolane

Application

This boronic ester is widely used in Suzuki-Miyaura cross-coupling reactions to form C-C bonds in medicinal chemistry and material science. It serves as a key intermediate in synthesizing pharmaceuticals, agrochemicals, and functionalized piperidine derivatives. Researchers also employ it in the development of boron-containing probes for biochemical studies.

Safety and Hazards

GHS Hazard Statements

• H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (25%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (25%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
• H413 (25%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P273, P280, 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. 4 (25%)
• Acute Tox. 4 (25%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (25%)
• STOT SE 3 (100%)
• Aquatic Chronic 4 (25%)

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