Description

(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acid (CAS No. 164014-95-3) is a high-purity boronic acid derivative with the molecular formula C₈H₉BO₄. This compound features a 2,3-dihydro-1,4-benzodioxin scaffold, making it a valuable building block in organic synthesis, particularly for Suzuki-Miyaura cross-coupling reactions. Its boronic acid functional group enables efficient formation of carbon-carbon bonds with aryl or vinyl halides, catalyzed by palladium complexes. The product is supplied as a white to off-white crystalline powder, rigorously tested for purity (typically ≥95% by HPLC or NMR), and is ideal for pharmaceutical, agrochemical, and materials science research. Store under inert conditions at 2-8°C to ensure stability.

Properties

• CAS Number: 164014-95-3
• Complexity: 176
• IUPAC Name: 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid
• InChI: InChI=1S/C8H9BO4/c10-9(11)6-1-2-7-8(5-6)13-4-3-12-7/h1-2,5,10-11H,3-4H2
• InChI Key: SQDUGGGBJXULJR-UHFFFAOYSA-N
• Exact Mass: 180.0593889
• Molecular Formula: C8H9BO4
• Molecular Weight: 179.97
• SMILES: B(C1=CC2=C(C=C1)OCCO2)(O)O
• Topological: 58.9
• Monoisotopic Mass: 180.0593889
• Synonyms: (2,3-dihydro-1,4-benzodioxin-6-yl)boronic acid, 625-755-9, 1,4-Benzodioxane-6-boronic acid, 164014-95-3, 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid, (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)boronic acid, MFCD01009696, Boronic acid, B-(2,3-dihydro-1,4-benzodioxin-6-yl)-, BORONIC ACID, (2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)-, 1,4-Benzodioxan-6-boronic acid, 3,4-(ethylenedioxy)benzeneboronic acid, 1,4-Benzodioxane-6-boronicacid, 2,3-dihydro-1,4-(benzodioxin-6-yl)boronic acid, SCHEMBL121851, DTXSID00379869, SQDUGGGBJXULJR-UHFFFAOYSA-N, 3,4-ethylenedioxyphenylboronic acid, ALBB-012243, BCP23246, CS-D1714, SBB018828, AKOS002659294, AB07964, 1,4-Benzodioxane-6-boronic acid, 96%, 3H-benzo[e]1,4-dioxin-6-boronic acid, NCGC00249476-01, AS-15068, BP-10782, HY-34511, SY021600, 2H,3H-benzo[e]1,4-dioxin-6-boronic acid, DB-010278, 2h,3h-benzo[e] 1,4-dioxin-6-boronic acid, B4181, EN300-212569, 2,3-Dihydro-1,4-benzodioxin-6-yl boronic acid, 2,3-dihydrobenzo[b][1,4]dioxin-6-ylboronic acid, 2,3-DIHYDRO-1,4-BENZODIOXINE-6-BORONIC ACID, Z381541022, 1,4-Benzodioxane-6-boronic acid (contains varying amounts of Anhydride)

Application

(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acid is widely used in palladium-catalyzed cross-coupling reactions to synthesize complex organic molecules, including pharmaceuticals and functional materials. Its benzodioxin core is a privileged structure in drug discovery, often found in compounds with CNS activity. Researchers also employ it to modify polymers or surfaces via boronic acid-mediated conjugation. The compound’s stability and reactivity make it suitable for high-throughput screening and combinatorial chemistry.

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 (97.9%): 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 (97.9%)

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