Description

4,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane (CAS No. 72824-04-5) is a highly versatile and reactive organoboron compound with the molecular formula C₉H₁₇BO₂. This pinacol boronic ester derivative is widely used in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, due to its stability and efficient transmetalation properties. The compound features a dioxaborolane ring with tetramethyl substitution, enhancing its steric and electronic properties for selective transformations. Its allyl group enables further functionalization, making it a valuable intermediate in pharmaceuticals, agrochemicals, and materials science. Supplied as a clear, colorless to pale yellow liquid, it is stored under inert conditions to maintain purity and reactivity. Ideal for researchers seeking high-precision boron reagents.

Properties

• CAS Number: 72824-04-5
• Complexity: 171
• IUPAC Name: 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3
• InChI Key: YMHIEPNFCBNQQU-UHFFFAOYSA-N
• Exact Mass: 168.1321599
• Molecular Formula: C9H17BO2
• Molecular Weight: 168.04
• SMILES: B1(OC(C(O1)(C)C)(C)C)CC=C
• Topological: 18.5
• Monoisotopic Mass: 168.1321599
• Synonyms: 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane, 672-877-3, Allylboronic acid pinacol ester, 72824-04-5, 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, Allylboronic acid, pinacol cyclic ester, 4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane, allyl boronic acid pinacol ester, PINACOLYL 2-PROPENYLBORONATE, 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (stabilized with Phenothiazine), MFCD00013347, Allylboronic acid, pinacol ester, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-propenyl)-, SCHEMBL838241, allyl-boronic acid pinacol ester, DTXSID70376784, YMHIEPNFCBNQQU-UHFFFAOYSA-N, AKOS000265360, Allylboronic acid pinacol ester, 97%, AB01126, CS-W000963, AS-11409, AS-81501, A2157, EN300-105979, A837633, 2-allyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane, Z1203162558, 4,4,5,5-tetramethyl-2-prop-2-en-1-yl-1,3,2-dioxaborolane

Application

4,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane is a key reagent in Suzuki-Miyaura cross-coupling reactions for constructing C-C bonds in complex organic molecules. It is widely employed in pharmaceutical research for synthesizing bioactive compounds and drug candidates. The allyl group allows for further modifications, such as hydroboration or polymerization, in materials science applications. Its stability and reactivity also make it suitable for catalytic cycles in asymmetric synthesis.

Safety and Hazards

GHS Hazard Statements

• H226 (98.3%): Flammable liquid and vapor [Warning Flammable liquids]
• H315 (81%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (81%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (79.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (98.3%)
• Skin Irrit. 2 (81%)
• Eye Irrit. 2 (81%)
• STOT SE 3 (79.3%)

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