Description

3,5-Dimethylisoxazole-4-boronic acid pinacol ester (CAS No. 832114-00-8) is a high-purity boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. With the molecular formula C₁₁H₁₈BNO₃, this compound features a stable pinacol boronate group attached to a 3,5-dimethylisoxazole scaffold, making it an excellent electrophile for C-C bond formation. Its IUPAC name is 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole. This reagent is supplied as a crystalline solid with exceptional batch-to-batch consistency, ensuring reliable performance in synthetic organic chemistry, medicinal chemistry, and materials science research. Store under inert conditions to maintain stability.

Properties

• CAS Number: 832114-00-8
• Complexity: 266
• IUPAC Name: 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole
• InChI: InChI=1S/C11H18BNO3/c1-7-9(8(2)14-13-7)12-15-10(3,4)11(5,6)16-12/h1-6H3
• InChI Key: CVLHETBAROWASE-UHFFFAOYSA-N
• Exact Mass: 223.1379736
• Molecular Formula: C11H18BNO3
• Molecular Weight: 223.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(ON=C2C)C
• Topological: 44.5
• Monoisotopic Mass: 223.1379736
• Synonyms: 3,5-Dimethylisoxazole-4-boronic acid pinacol ester, 3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole, 675-095-0, 832114-00-8, 3,5-Dimethylisoxazole-4-boronic acid, pinacol ester, 3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)isoxazole, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole, 3,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole, MFCD05863910, SCHEMBL174783, C11H18BNO3, DTXSID80374433, CVLHETBAROWASE-UHFFFAOYSA-N, (3,5-DIMETHYLISOXAZOL-4-YL)BORONIC ACID PINACOL ESTER, CS-D1108, BBL102968, SBB071324, STL556777, AKOS015907286, PB15817, SB10007, NCGC00662841-01, AC-24012, DS-13702, HY-78197, PD199939, SY031776, DB-010519, D3772, EN300-155894, 3,5-dimethylisoxazole-4-boronic acid pinacolester, 3,5-Dimethyl-4-isoxazoleboronic Acid Pinacol Ester, Z1695772846, 3,5-Dimethylisoxazole-4-boronic acid pinacol ester, 97%, (3,5-Dimethyl-4-isoxazolyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(3,5-dimethylisoxazol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoxazole, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)isoxazole, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)isoxazole, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-isoxazole, ISOXAZOLE, 3,5-DIMETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-

Application

3,5-Dimethylisoxazole-4-boronic acid pinacol ester is primarily employed in palladium-catalyzed cross-coupling reactions to introduce the 3,5-dimethylisoxazole moiety into complex molecules. It serves as a key building block for pharmaceutical intermediates, agrochemicals, and functional materials. The compound’s stability and reactivity make it ideal for synthesizing heterocyclic compounds in drug discovery programs. Researchers also utilize it in the development of boron-containing probes for chemical biology studies.

Safety and Hazards

GHS Hazard Statements

• H302 (37.5%): 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]

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 (37.5%)
• Acute Tox. 4 (25%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• Acute Tox. 4 (25%)
• STOT SE 3 (100%)

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