Description

2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 517874-21-4) is a high-purity boronic ester derivative with the molecular formula C₁₄H₁₉BO₄. This compound features a 1,4-benzodioxane core functionalized with a pinacol boronate ester group, making it a versatile intermediate in organic synthesis and cross-coupling reactions. Its stable dioxaborolane ring enhances reactivity in Suzuki-Miyaura couplings, while the benzodioxin moiety offers unique electronic properties for pharmaceutical and materials science applications. This product is supplied as a white to off-white crystalline solid with ≥95% purity (HPLC), ensuring optimal performance in research and industrial processes. Store under inert conditions to maintain stability.

Properties

• CAS Number: 517874-21-4
• Complexity: 328
• IUPAC Name: 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)10-5-6-11-12(9-10)17-8-7-16-11/h5-6,9H,7-8H2,1-4H3
• InChI Key: WIIBAHCYWOUFRM-UHFFFAOYSA-N
• Exact Mass: 262.1376392
• Molecular Formula: C14H19BO4
• Molecular Weight: 262.11
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)OCCO3
• Topological: 36.9
• Monoisotopic Mass: 262.1376392
• Synonyms: 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 674-915-4, 517874-21-4, 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 1,4-benzodioxane-6-boronic acid, pinacol ester, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzo-1,4-dioxoline, 1,4-Benzodioxane-6-boronic acid pinacol ester, MFCD05663890, SCHEMBL14212260, DTXSID60375246, WIIBAHCYWOUFRM-UHFFFAOYSA-N, SBB102511, (2,3-DIHYDROBENZO[B][1,4]DIOXIN-6-YL)BORONIC ACID PINACOL ESTER, AKOS015951058, AB22036, AS-2970, FT160590, CS-0094700, EN300-212568, Z1336745096, 1,4-Benzodioxane-6-boronic acid, pinacol ester, AldrichCPR, 2,3-Dihydro-1,4-benzodioxine-6-boronic acid, pinacol ester, 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzo[1,4]dioxine, 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzodioxine, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H,3H-benzo[e]1,4-dioxane

Application

This compound is widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl structures in medicinal chemistry. It serves as a precursor for functionalized 1,4-benzodioxane derivatives with potential applications in drug discovery and material science. The boronate ester group enables efficient carbon-carbon bond formation under mild conditions, making it valuable for constructing complex organic molecules.

Safety and Hazards

GHS Hazard Statements

• H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (75%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (75%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, 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 (75%)
• Acute Tox. 4 (50%)
• Skin Irrit. 2 (75%)
• Eye Irrit. 2A (75%)
• Acute Tox. 4 (50%)
• STOT SE 3 (75%)

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