Description

Cyclohexylboronic acid, pinacol ester (CAS: 87100-15-0) is a highly versatile organoboron compound with the molecular formula C₁₂H₂₃BO₂. This crystalline solid is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry, due to its stability and reactivity. Its pinacol ester structure enhances shelf-life and handling convenience, making it a preferred choice for researchers. With a purity typically exceeding 97%, this reagent is ideal for pharmaceutical intermediates, agrochemical synthesis, and material science applications. Stored under inert conditions, it ensures consistent performance in palladium-catalyzed transformations.

Properties

• CAS Number: 87100-15-0
• Complexity: 216
• IUPAC Name: 2-cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C12H23BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h10H,5-9H2,1-4H3
• InChI Key: OUEVCDGYTKLNMJ-UHFFFAOYSA-N
• Exact Mass: 210.1791101
• Molecular Formula: C12H23BO2
• Molecular Weight: 210.12
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2CCCCC2
• Topological: 18.5
• Monoisotopic Mass: 210.1791101
• Synonyms: Cyclohexylboronic acid, pinacol ester, 814-148-6, 87100-15-0, 2-cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, CYCLOHEXYLBORONIC ACID PINACOL ESTER, MFCD04038749, 1,3,2-Dioxaborolane, 2-cyclohexyl-4,4,5,5-tetramethyl-, SCHEMBL5683205, DTXSID80394853, (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane, AKOS015907186, AB17172, DS-17414, SY033735, DB-016118, C3101, CS-0029524, EN300-1706276, 2-Cyclohexyl-4,4,5,5-tetramethyl -1,3,2-dioxaborolane, 2-Cyclohexyl-4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolane

Cyclohexylboronic acid pinacol ester is a key reagent in Suzuki-Miyaura cross-coupling reactions, enabling the formation of C-C bonds in complex organic syntheses. It is particularly valuable in pharmaceutical research for constructing cyclohexyl-containing scaffolds. The compound’s stability under aerobic conditions simplifies laboratory handling compared to boronic acids. Its applications extend to polymer chemistry and the development of liquid crystals.

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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